Information on EC 3.1.6.2 - steryl-sulfatase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
3.1.6.2
-
RECOMMENDED NAME
GeneOntology No.
steryl-sulfatase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O = 3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of sulfuric ester
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Steroid hormone biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
steryl-sulfate sulfohydrolase
Also acts on some related steryl sulfates.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3-beta-hydroxysteroid sulfate sulfatase
-
-
-
-
arylsulfatase C
-
-
-
-
ASC
-
-
-
-
dehydroepiandrosterone sulfatase
-
-
-
-
dehydroepiandrosterone sulfate sulfatase
-
-
-
-
phenolic steroid sulfatase
-
-
-
-
pregnenolone sulfatase
-
-
-
-
steroid 3-sulfatase
-
-
-
-
steroid sulfatase
-
-
-
-
steroid sulfate sulfohydrolase
-
-
-
-
sterol sulfatase
-
-
-
-
Steryl-sulfate sulfohydrolase
-
-
-
-
sulfatase, sterol
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
9025-62-1
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
2-2.5 years old females
-
-
Manually annotated by BRENDA team
Haliotis sp.
abalone entrails
-
-
Manually annotated by BRENDA team
snail
-
-
Manually annotated by BRENDA team
2 forms of arylsulfatase C: slow form, fast form, only slow form is associated with sterol sulfatase activity; fast form in patients with X-linked ichthyosis
-
-
Manually annotated by BRENDA team
colon carcinoma cells
-
-
Manually annotated by BRENDA team
enzyme does not copurify with oestrone sulfate sulfohydrolase
-
-
Manually annotated by BRENDA team
expression in COS-1 cell
-
-
Manually annotated by BRENDA team
native enzyme and recombinant enzyme from CHO cells
-
-
Manually annotated by BRENDA team
patients with endometrial carcinoma
-
-
Manually annotated by BRENDA team
patients with endometriosis
-
-
Manually annotated by BRENDA team
patients with estrogen-receptor positive metastatic breast cancer
-
-
Manually annotated by BRENDA team
recombinant enzyme
-
-
Manually annotated by BRENDA team
women
-
-
Manually annotated by BRENDA team
athymic female MF-1 nude mice
-
-
Manually annotated by BRENDA team
hydrophobic form appears to be identical to steroid sulfatase, hydrophilic form: no steroid sulfatase activity
-
-
Manually annotated by BRENDA team
intact, athymic, female MF-1 nude mice (in vivo tumor growth model), ovariectomized, athymic, female MF-1 nude mice (hormone-dependent in vivo tumor growth model)
-
-
Manually annotated by BRENDA team
keyhole limpet
-
-
Manually annotated by BRENDA team
mollusc
-
-
Manually annotated by BRENDA team
adult Wistar female ovariectomized rats
-
-
Manually annotated by BRENDA team
female adult Wistar rats
-
-
Manually annotated by BRENDA team
female Wistar rats
-
-
Manually annotated by BRENDA team
immature female Sprague-Dawley rats
-
-
Manually annotated by BRENDA team
immature female Wistar rats
-
-
Manually annotated by BRENDA team
ovarectomised animal
-
-
Manually annotated by BRENDA team
ovariectomised female Wistar rats
-
-
Manually annotated by BRENDA team
Sus scrofa steroid sulfatase (StS) mRNA, partial cds from boar testis; 5 age groups 50, 100, 150, 250 days old boars, remarkably high testicular estrogen output
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
deletion of the STS gene is associated with atypical X-linked ichthyosis
malfunction
-
STS deficiency is an X-linked recessive, generally mild chronic disorder that presents clinically in the first year of life as scaly skin (ichthyosis)
malfunction
-
hormone-dependent breast cancer might be effectively treated by dual inhibition of aromatase and steroid sulfatase
malfunction
-
steroid sulfatase/estrogen sulfotransferase status is associated with intratumoral estrogen level in the colon carcinoma, and steroid sulfatase-negative/estrogen sulfotransferase-positive colon carcinoma patients have longer survival. STS mRNA expression is higher in breast carcinoma tissues than that in normal breast tissues, and it is significantly associated with the breast carcinoma progression and poor clinical outcome of the patients
metabolism
-
conversion of estrone sulfate to estrone is a non-aromatase-based route to estrone and estradiol in postmenopausal women
physiological function
-
activation of steroid sulfatase pathway due to increment in steroid sulfatase and/or decrement in estrogen sulfotransferase expressions plays important role in their estrogen-dependent growth
physiological function
-
steroid sulfatase controls the levels of 3-hydroxysteroids available from circulating steroid sulfates in several normal and malignant tissues
metabolism
-
relevance and interplay between aromatase, steroid sulfatase, organic anion transporting polypeptide B, and 17beta-hydroxysteroid dehydrogenase type 1 to facilitate local synthesis of estrogenic steroids within breast and other tissues, pathways of local synthesis of estrogenic steroids in neoplastic breast tissue, overview
additional information
-
active site residues are D35, D36, FGS75, R79, K134, H136, H290, D342, Q343, and K368
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
16alpha-hydroxydehydroepiandrosterone 3-sulfate + H2O
16alpha-hydroxydehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
17beta-estradiol sulfate + H2O
17beta-estradiol + sulfate
show the reaction diagram
-
-
-
-
?
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O
3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
-
-
-
-
-
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O
3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
-
-
-
-
?
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O
3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
-
-
-
-
-
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O
3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
-
-
-
-
-
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
-
both s-form and f-form
-
-
-
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferol + sulfate
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl-6-O-sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl sulfate + H2O
4-nitrophenol + sulfate
show the reaction diagram
-
-
-
-
?
7-dehydroepiandrosterone sulfate + H2O
7-dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
androstenediol sulfate + H2O
androstenediol + sulfate
show the reaction diagram
-
-
-
-
?
androstenediol-3-sulfate + H2O
androstenediol + sulfate
show the reaction diagram
-
-
-
-
?
arylsulfates + H2O
? + sulfate
show the reaction diagram
-
e.g. 3alpha sulfates of: 5alpha-androstane-17-one, 5beta-androstane-17-one, 3beta sulfates of: 5alpha-androstane-17-one, DELTA5-androstene 17-one, 5alpha-pregnane-20-one, DELTA5-pregnene-20-one
-
-
?
arzoxifene sulfate + H2O
arzoxifene + sulfate
show the reaction diagram
-
product of sulfotransferase reaction on arzoxifene used in hormone replacement therapy
-
-
?
beta-estradiol-3-sulfate + H2O
estradiol + sulfate
show the reaction diagram
-
-
-
-
?
cholesterol 3-sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
-
-
-
?
cholesterol 3-sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
-
-
-
?
cholesterol 3-sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
only s-form
-
-
-
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
-
-
-
?
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
cholesterol sulfate metabolism, steroid sulfohydrolase pathway, highly specific for cholesterol sulfate
-
-
?
cortisone 21-sulfate + H2O
cortisone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroandrosterone 3-sulfate + H2O
dehydroandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroandrosterone 3-sulfate + H2O
dehydroandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
P08842
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
only s-form
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
P08842
in adipose tissue, further concersion to bioactive androgens and estrogens
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
conversion to androstenediol by 17beta-hydroxysteroid dehydrogenase type 1, androstenediol supports mammary tumor growth in rodents, or conversion to androstenedione, main substrate for aromatase in postmenopausal women
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to andgrogen testosterone or androstenediol, androgens stimulate growth of prostate cancer cells
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to androst-5-ene-3beta,17beta-diol (Adiol), an androgen with estrogenic properties, and thus a mitogen for the growth and development of hormome-dependent breast cancer
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to androst-5-ene-3beta,17beta-diol, an androgen with estrogenic properties, stimulating breast cancer growth
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol with 3beta-hydroxysteroid dehydrogenase, aromatase and 17beta-hydroxysteroid dehydrogenase
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to testosterone or aromatisation to estrone
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to testosterone
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
androgen metabolism, dehydroepiandrosterone sulfate may play a part in the pathogenesis of androgenic alopecia
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
hydrolyzes dehydroepiandrosterone sulfate to its active, unsulfated form
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
oestrogen biosynthesis
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
1.5% of the activity with cholesterol sulfate
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
dehydroepiandrosterone is reduced to a diol by 17beta-HSD1, apart from estrone, the steroid sulfatase pathway is also responsible for the production of another steroid with estrogenic properties, namely androstenediol
-
-
?
dehydroisoandrosterone 3-sulfate + H2O
dehydroisoandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
epiandrosterone 3-sulfate + H2O
epiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
-
hydrolyzes estrone 3-sulfate to its active, unsulfated form
-
-
?
estrone sulfate
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
-
-
-
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
Q45FD5
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
conversion to estradiol by 17beta-hydroxysteroid dehydrogenase type 1
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
estrogen estrone formed from androstenedione by cytochrome P450 enzyme aromatase, estrogen is a mitogen for growth and development of hormone-dependent breast cancer
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
in breast cancer tissue 10 times more estrone originates from estrone sulfate than from androstenedione
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to biologically active estrogen estradiol, increased activity and expression of STS in hormone-dependent cancer cells, estradiol prerequisite for Ishikawa cell tumorgenesis in ovariectomized mouse model, estrogens are suggested as growth stimulators in prostate cancer cells as well
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol with 17beta-hydroxysteroid dehydrogenase
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
natural substrate
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
only s-form
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
STS converts the major circulating plasma estrogen estrone sulfate into the biologically active estrogene estrone, STS plays an important role in the in situ estrogen actions of various sex steroid-dependent tumors, peripheral STS plays a very important role in peripheral estrogen metabolism and actions in the human fetus
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
STS plays an important role in the in situ estrogen actions of estrogen-dependent human tissues and various sex steroid-dependent tumors, STS may be associated with the degree of atherosclerotic changes in the female aorta, transformation of the biologically inactive form of plasma estrogen in its active form
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
0.6% of the activity with cholesterol sulfate
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
Q45FD5
STS within the Leydig cells of Sus scrofa is involved in modulation of testicular estrogen bioavailability
-
-
?
p-acetylphenyl sulfate + H2O
p-acetylphenol + sulfate
show the reaction diagram
-
-
-
-
?
p-nitrocatechol sulfate + H2O
nitrocatechol + sulfate
show the reaction diagram
-
-
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
-
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
-
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
-
-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
-
-
?
phenolphthalein disulfate + H2O
phenolphthalein monosulfate + sulfate
show the reaction diagram
-
-
-
-
?
pregnenolone 3-sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
-
-
-
-
?
pregnenolone sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
-
-
-
-
-
pregnenolone sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
-
-
-
-
?
pregnenolone sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
-
8.7% of the activity with cholesterol sulfate
-
-
?
raloxifene sulfate + H2O
raloxifene + sulfate
show the reaction diagram
-
product of sulfotransferase reaction on raloxifene used in hormone replacement therapy, the benzothiophene sulfate is substrate, the 4'-phenolic sulfate is no substrate for enzyme
-
-
?
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
-
-
-
-
?
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
-
steroid sulfatase converts all steroid sulfates into their free steroid forms
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
testosterone 3-sulfate + H2O
testosterone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
estrone is locally produced from circulating inactive estrone sulfate by steroid sulfatase
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
not: dichlorophenoxyethyl sulfate
-
-
?
additional information
?
-
-
not: 17-sulfate ester of beta-estradiol or delta4-androstene-3-one-17alpha-ol
-
-
?
additional information
?
-
-
not: androsterone 3-sulfate, higher activity for 16-unsubstituted than for 16alpha-hydroxylated substrates
-
-
?
additional information
?
-
-
biosynthesis of estrogens in breast tumor tissues of post-menopausal breast cancer patients, STS stimulates the growth and survival of estrogen-dependent breast tumors
-
-
-
additional information
?
-
-
ES is a component of the three-enzyme system that has been implicated in intracrine biosynthesis of estradiol, hence, proliferation of hormone-dependent breast tumors
-
-
-
additional information
?
-
-
in vivo the activity of STS in the mammary myoepithelial cells may influence the availability of active, unsulfated hormones to the adjacent epithelial cells within mammary tissue and may have a role in the regulation of mammary growth and development
-
-
-
additional information
?
-
-
NSS likely plays a key role in the regulation of the GABA-A receptor
-
-
-
additional information
?
-
-
ovarian estrogen synthesis, the relative contribution of STS activity to ovarian steroidogenesis is unclear but may have important physiological and pathophysiological implications
-
-
-
additional information
?
-
-
steroid sulfatase in the fallopian tube may be involved in controlling the local steroid environment, which appears to regulate aspects of the physiological reproductive function of the fallopian tube
-
-
-
additional information
?
-
-
STS may play an important role within the CNS
-
-
-
additional information
?
-
-
STS stimulates steroid production and increases steroidogenic acute regulatory protein expression
-
-
-
additional information
?
-
-
the action of STS makes a major contribution to the in situ estrogen production in breast tumors
-
-
-
additional information
?
-
-
desulfates a number of 3beta-hydroxysteroid sulfates
-
-
-
additional information
?
-
-
enzyme is responsible for the removal of the sulfamoyl group from oestrogen sulfamates
-
-
-
additional information
?
-
-
enzyme may be involved in the quality of eggs in patients with endometriosis
-
-
-
additional information
?
-
-
no substrate: tibolone 17-sulfate
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
cholesterol sulfate metabolism, steroid sulfohydrolase pathway
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
P08842
in adipose tissue, further concersion to bioactive androgens and estrogens
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
conversion to androstenediol by 17beta-hydroxysteroid dehydrogenase type 1, androstenediol supports mammary tumor growth in rodents, or conversion to androstenedione, main substrate for aromatase in postmenopausal women
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to andgrogen testosterone or androstenediol, androgens stimulate growth of prostate cancer cells
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to androst-5-ene-3beta,17beta-diol (Adiol), an androgen with estrogenic properties, and thus a mitogen for the growth and development of hormome-dependent breast cancer
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to androst-5-ene-3beta,17beta-diol, an androgen with estrogenic properties, stimulating breast cancer growth
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol with 3beta-hydroxysteroid dehydrogenase, aromatase and 17beta-hydroxysteroid dehydrogenase
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
subsequent conversion to testosterone or aromatisation to estrone
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
androgen metabolism, dehydroepiandrosterone sulfate may play a part in the pathogenesis of androgenic alopecia
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
hydrolyzes dehydroepiandrosterone sulfate to its active, unsulfated form
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
oestrogen biosynthesis
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
-
dehydroepiandrosterone is reduced to a diol by 17beta-HSD1, apart from estrone, the steroid sulfatase pathway is also responsible for the production of another steroid with estrogenic properties, namely androstenediol
-
-
?
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
-
hydrolyzes estrone 3-sulfate to its active, unsulfated form
-
-
?
estrone sulfate
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
conversion to estradiol by 17beta-hydroxysteroid dehydrogenase type 1
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
estrogen estrone formed from androstenedione by cytochrome P450 enzyme aromatase, estrogen is a mitogen for growth and development of hormone-dependent breast cancer
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
in breast cancer tissue 10 times more estrone originates from estrone sulfate than from androstenedione
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to biologically active estrogen estradiol, increased activity and expression of STS in hormone-dependent cancer cells, estradiol prerequisite for Ishikawa cell tumorgenesis in ovariectomized mouse model, estrogens are suggested as growth stimulators in prostate cancer cells as well
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
-
subsequent conversion to estradiol with 17beta-hydroxysteroid dehydrogenase
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
natural substrate
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
STS converts the major circulating plasma estrogen estrone sulfate into the biologically active estrogene estrone, STS plays an important role in the in situ estrogen actions of various sex steroid-dependent tumors, peripheral STS plays a very important role in peripheral estrogen metabolism and actions in the human fetus
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
STS plays an important role in the in situ estrogen actions of estrogen-dependent human tissues and various sex steroid-dependent tumors, STS may be associated with the degree of atherosclerotic changes in the female aorta, transformation of the biologically inactive form of plasma estrogen in its active form
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
Q45FD5
STS within the Leydig cells of Sus scrofa is involved in modulation of testicular estrogen bioavailability
-
-
?
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
-
-
-
-
?
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
-
steroid sulfatase converts all steroid sulfates into their free steroid forms
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
-
estrone is locally produced from circulating inactive estrone sulfate by steroid sulfatase
-
-
?
additional information
?
-
-
biosynthesis of estrogens in breast tumor tissues of post-menopausal breast cancer patients, STS stimulates the growth and survival of estrogen-dependent breast tumors
-
-
-
additional information
?
-
-
ES is a component of the three-enzyme system that has been implicated in intracrine biosynthesis of estradiol, hence, proliferation of hormone-dependent breast tumors
-
-
-
additional information
?
-
-
in vivo the activity of STS in the mammary myoepithelial cells may influence the availability of active, unsulfated hormones to the adjacent epithelial cells within mammary tissue and may have a role in the regulation of mammary growth and development
-
-
-
additional information
?
-
-
NSS likely plays a key role in the regulation of the GABA-A receptor
-
-
-
additional information
?
-
-
ovarian estrogen synthesis, the relative contribution of STS activity to ovarian steroidogenesis is unclear but may have important physiological and pathophysiological implications
-
-
-
additional information
?
-
-
steroid sulfatase in the fallopian tube may be involved in controlling the local steroid environment, which appears to regulate aspects of the physiological reproductive function of the fallopian tube
-
-
-
additional information
?
-
-
STS may play an important role within the CNS
-
-
-
additional information
?
-
-
STS stimulates steroid production and increases steroidogenic acute regulatory protein expression
-
-
-
additional information
?
-
-
the action of STS makes a major contribution to the in situ estrogen production in breast tumors
-
-
-
additional information
?
-
-
enzyme is responsible for the removal of the sulfamoyl group from oestrogen sulfamates
-
-
-
additional information
?
-
-
enzyme may be involved in the quality of eggs in patients with endometriosis
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(12aS)-N,N-dihydroxy-12a-methyl-1,3-dioxo-2-propyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinoline-8-sulfinamide
-
-
(17beta)-17-(2,3,4,5,6-pentafluorobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(2-furylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3,5-dibromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-benzyloxybenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-methyl-2-thienyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-tert-butylbenzyl)estra-1(10),2,4-triene-3,17-diol
-
estradiol phenolic reversible inhibitor as reference, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 39% inhibition, at 1 microM 62% inhibition
(17beta)-17-(4-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(cyclohexylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(cyclopropylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(pyridin-3-ylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-benzyl-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-benzylestra-1(10),2,4-triene-3,17-diol
-
estradiol phenolic reversible inhibitor as reference, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 15% inhibition, at 1 microM 48% inhibition
(17beta)-17-[3,5-bis(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3,5-bis(tert-butyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3,5-bis(trifluoromethyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3-(dibenzylamino)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[4-(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-{[2-(2-bromoethyl)cyclopropyl]methyl}estra-1(10),2,4-triene-3,17-diol
-
-
(17beta,17'beta)-17,17'-(2E)-but-2-ene-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
-
reversible non-competitive or mixed inhibition, estradiol dimer with C17-C17 bond, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 42% inhibition, at 1 microM 56% inhibition
(17beta,17'beta)-17,17'-butane-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
-
reversible non-competitive or mixed inhibition, estradiol dimer with C17-C17 bond, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 30% inhibition, at 1 microM 54% inhibition
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)(oxo)acetic acid
-
-
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)acetic acid
-
-
(NH4)2SO4
-
slight
(p-O-sulfamoyl)-N-tetradecanoyl tyramine
-
DU-14, in vivo, increase in hippocampal acetylcholine
(p-O-sulfamoyl)-N-tetradecanoyl tyramine
-
non-estrogenic STS inhibitor, IC50: 56 nM/l, anti-cancer activity
(R)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
pure R(+)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
(S)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
pure S(-)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-indanone 4-O-sulfamate
-
-
1-indanone 5-O-sulfamate
-
-
1-indanone 6-O-sulfamate
-
-
1-tetralone 6-O-sulfamate
-
-
1-tetralone 7-O-sulfamate
-
-
1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
bromo derivative of 1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole does improve aromatase inhibitory activity
1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
meta-chloro derivative of 1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole does increase aromatase inhibition activity
1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
increase of aromatase inhibitory activity due to presence of a para-cyanophenyl moiety
1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
best dual inhibition
1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole
-
methoxy groups reduce inhibition of aromatase compared to 1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
sulfamate in meta-position increases aromatase inhibition strength compared to para-position
1-[bis-(4-sulfamoyloxy-3-methoxyphenyl)methyl]-1H-[1,2,4]triazole
-
exchange in positions of methoxy and sulfamate group compared to 1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole fails to improve aromatase inhibitory activity
16alpha-hydroxydehydroepiandrosterone
-
competitive to dihydroepiandrosterone
17-oxoestra-1,3,5(10)-trien-3-yl sulfamate
-
-
17alpha-benzyl-17beta-hydroxyestra-1,3,5-(10)-triene-3-boronic acid
-
-
17alpha-benzyl-3,17beta-dihydroxyestra-1,3,5-(10)-triene
-
-
17beta estradiol
-
exposure to 17beta estradiol causes 70% reduction of estrone 3-sulfate sulfatase activity in MCF-7 cells after 6 days, but 9% increase in mammary myoepithelial cells
19,19-difluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
-
-
19-fluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
-
-
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
-
-
2-(1-adamantyl)-4-oxo-4H-chromen-6-yl sulfamate
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carbaldehyde
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxamide
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylic acid
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromen-6-yl sulfamate
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carbonitrile
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carboxylic acid
-
-
2-(1-adamantyl)-6-(hydroxymethyl)-4H-chromen-4-one
-
-
2-(1-adamantyl)-6-glycoloyl-4H-chromen-4-one
-
-
2-(difluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
-
-
2-(fluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
-
-
2-bromo-4-[(R)-(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]-N,N-dihydroxybenzenesulfinamide
-
-
2-formyl-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
time- and concentration-dependent inhibitor, shows more or less pseudo-first order behavior at all concentrations
2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
-
2-methoxyestrone-3-O-sulfamate
-
potent active site-directed inhibitor, no effect on STS mRNA expression in fibroblasts
2-phenylindole sulfamate
-
2-phenylindole sulfamates with lipophilic side chains in 1- or 5-position of the indole with IC50-values between 2 nM and 0.001 mM, irreversibly inhibits hydrolysis of estrone sulfate in MDA-MB 231 cells, inhibits gene activation in estrogen receptor-positive MCF-7 breast cancer cells in submicromolar concentrations and reduces cell proliferation with IC50 of 0.001 mM
2-t-butyl-4H-1-benzopyran-4-one-6-boronic acid
-
-
2-tert-butyl-6-hydroxy-4H-chromen-4-one
-
-
2-[3-[[(4-[[(aminooxy)sulfinyl]oxy]phenyl)sulfanyl]methyl]-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
-
-
2H1-benzpyran 7-O-disulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
-
68.2% inhibition at 0.01 mM
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
-
-
3'-chloro-5-(1H-1,2,4-triazol-1-ylmethyl)biphenyl-2-carbonitrile
-
-
3,4,8-trimethylcoumarin 7-O-sulfamate
-
-
-
3,4-dihydro-4-methylcoumarin 7-O-sulfamate
-
-
3,4-dihydrocoumarin 7-O-sulfamate
-
-
3,4-dimethylcoumarin 7-O-sulfate
-
12-fold more potent than COUMATE
3-nitrophenyl sulfamate
-
-
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
-
-
3-sulfamoyloxy-N-(1''-pyridin-3''-ylmethyl)-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
-
highly potent, long-acting, nonestrogenic steroid sulfatase inhibitor with inhibitory properties to human carbonic anhydrase II, thus enabling transport by erythorcytes, no estrogenic effects observed in uterine weight gain study with ovariectomized Wistar rats, 24 h after last dose of 4 days of oral administration of 10 mg/kg/d, in vivo: single dose of 0.1 mg/kg 48% inhibition of liver steroid sulfatase activity, 0.5 and 1 mg/kg total inhibition, activity measured 24 h after dose administration, recovery of steroid sulfatase acitivity after single oral dose of 10 mg/kg: complete inhibition till day 5, day 17: 50% recovery, day 28: complete recovery
3-sulfamoyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
4-(trifluoromethyl)coumarin 7-O-sulfamate
-
-
4-fluoro-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
linear mixed-type inhibition, compound is capable of binding at sites both within and outside the active site
4-methylcoumarin 6,7-O,O-disulfamate
-
-
4-methylcoumarin 7-O-sulfamate
-
COUMATE, also in vivo
4-methylcoumarin-7-O-sulfamate
-
-
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
-
-
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
-
665 COUMATE, placental IC50: 200 nM
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-(N,N-dimethyl)sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-(N-methyl)sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-sulfamate
-
-
5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
5-((1H-1,2,4-triazol-1-yl)methyl)-3'-chloro-4'-hydroxybiphenyl-2-carbonitrile
-
-
5-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile
-
-
5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
5-pregnen-3beta,21-diol
-
most potent inhibitor of C21 steroids
5-pregnen-3beta,21-diol-20-one
-
most potent inhibitor of C21 steroids
5alpha-androstane-3alpha-17beta-diol
-
most potent inhibitor of C19 steroids
6-(3-phenylpropoxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-(pentyloxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-methoxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-methoxycoumarin 7-O-sulfamate
-
-
6-oxo-5-(3-phenylpropyl)-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-5-pentyl-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
-
6612 COUMATE, placental IC50: 60 nM
6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
-
6610 COUMATE, placental IC50: 1 nM
6-oxo-7,8,9,10,11,12-hexahydro-6H-cycloocta[c]chromen-3-yl sulfamate
-
i.e. STW64, treatment of postmenopausal women with estrogen receptor-positive metastatic breast cancer. Inhibitor almost completely blocks enzyme activty in peripheral blood lymphocytes and tumor tissues, inhibition is associated with significant reductions in serum concentrations of androstenediol and estrogens. Serum androstenedione concentration also decreases by up to 86%
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
-
668 COUMATE, placental IC50: 30 nM
6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
-
666 COUMATE, placental IC50: 70 nM
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
-
6613 COUMATE, placental IC50: 75 nM
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
-
6611 COUMATE, placental IC50: 13 nM
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
-
669 COUMATE, placental IC50: 2.4 nM
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
667 COUMATE, placental IC50: 8 nM
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
6,6,7-COUMATE, IC50: 5.1 nM in JEG-3 cells, 0.43 nM in MCF-7 cells
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
6,6,7-COUMATE, potent inhibitor, in vivo inhibition study, more inhibitory than TX-1299
6-oxo-8,9,10,11-tetrahydro-7H-cylohepta-[c][1]benzopyran-boronic acid
-
-
667 COUMATE
-
i.e. 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta(c)chromen-3-yl sulfamate, coadministation of oestrone sulfamate and 667 COUMATE completely blocks enzyme activity and completely abrogates the ability of oestrone sulfamate to stimulate uterine growth
667-coumate
-
-
7,8-dihydronaphthalene 2-O-sulfamate
-
-
7-hydroxy-4-methylcoumarin 6-O-sulfamate
-
-
AgNO3
-
slight
AgNO3
-
5 mM, 65% inhibition
Ammonium molybdate
-
10 mM, 20% residual activity
anastrozole
-
-
breast cyst fluid
-
-
-
CaCl2
-
slight
calcium chloride
-
5 mM, 36% residual activity
cholesterol
-
1 mM, 57% inhibition
Cl-
-
slight
coumarin 7-O-sulfamate
-
-
cysteine
-
10 mM, 15% inhibition
daidzein-4'-O-sulfate
-
at 0.005 mM
daidzein-7,4'-di-O-sulfate
-
at 0.001 mM
dehydroepiandrosterone
-
competitive to 16alpha-hydroxydehydroepiandrosterone
dehydroepiandrosterone
-
-
dithiothreitol
-
5 mM, 45% residual activity
EDTA
-
10% inhibition at 1 mM
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
competitive
estrone 3-O-sulfamate
-
-
Estrone 3-sulfate
-
competitive inhibitor
Estrone 3-sulfate
-
-
estrone-3-O-(N,N-dimethyl)sulfamate
-
-
estrone-3-O-(N-methyl)sulfamate
-
-
estrone-3-O-methylthiophosphonate
-
-
estrone-3-O-sulfamate
-
EMATE, most potent, irreversible
estrone-3-O-sulfamate
-
active site-directed inhibitor; EMATE, most potent, irreversible
estrone-3-O-sulfamate
-
active site-directed inhibitor; also in vivo; EMATE, most potent, irreversible
estrone-3-O-sulfamate
-
potent inhibitor, dose-dependent, maximum inhibition between 100 and 1000 nM
estrone-3-O-sulfamate
-
specific inhibitor, concentration-dependent, complete inhibition at 0.1 mM, 100 nM and 10 nM, 89% inhibition at 1 nM
estrone-3-O-sulfamate
-
highly potent, specific STS inhibitor, complete inhibition at 0.001 mM
estrone-3-O-sulfamate
-
-
estrone-3-O-sulfamate
-
-
estrone-3-sulfamate
-
best inhibitor, IC50: 3.2 nM in JEG-3 cells, 0.08 nM in MCF-7 cells
estrone-3-sulfamate
-
potent estrone sulfatase inhibitor that causes irreversible inactivation of the enzyme
glucose
-
slight
glutathione
-
reduced form, 5 mM, 23.5% residual activity
H2PO4-
-
-
human pituitary luteinizing hormone
-
human pituitary LH, reduces activity to 85% of baseline at 5 ng/ml, dose-dependent
-
Interleukin-1beta
-
marked inhibition of mRNA expression and STS activity
-
irosustat
-
i.e. STX64, BN83495, structure-activity relationship study. The inhibitor is used in clinical trials for patients with advanced hormone-dependent cancer
irosustat
-
i.e. BN83495
KBr
-
slight
KCl
-
slight
KCN
-
slight
KH2PO4
-
5 mM, 25% inhibition
KW-2581
-
active site-directed irreversible steroidal inhibitor
letrozole
-
-
LiCl
-
slight
Metabisulfite
-
-
methyl 2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylate
-
-
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
-
N,N-dimethoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
-
N-acetylated estrone 3-O-sulfamate
-
inhibits the enzyme irreversibly, albeit much less potently than estrone 3-O-sulfamate
Na-metaborate
-
-
Na-tetraborate
-
-
Na-tetraborate
-
-
Na2SO3
-
slight
Na2SO3
-
5 mM, 43% inhibition
Na2SO4
-
slight
Na2SO4
-
5 mM, 18% inhibition
NaCl
-
slight
NaF
-
slight
NaHSO3
-
slight
p-Nitrophenyl sulfate
-
noncompetitive inhibitor, dehydroepiandrosterone 3-sulfate as substrate
phosphate
-
-
phosphate
Haliotis sp.
-
abalone sulfatases is inhibited by phosphate buffer: 15% activity in 5 mM K2HPO4/KH2PO4, pH 7
phosphate
-
limpet sulfatase is inhibited by phosphate buffer: 4% activity in 5 mM K2HPO4/KH2PO4, pH 7
pregnenolone
-
1 mM, 10% inhibition
pregnenolone 3-sulfate
-
competitive inhibitor, dehydroepiandrosterone 3-sulfate as substrate
Rose bengal
-
histidine modification
Sodium arsenite
-
slight
Sodium deoxycholate
-
-
sodium taurocholate
-
-
Steroids
-
overview, e.g. estrone, estradiol, C21 steroids, C19 steroids
Steroids
-
overview, e.g. estrone, estradiol, C21 steroids, C19 steroids
STX213
-
phenol sulfamate pharmacophore, irreversible total inhibition from 10-1000 nM in Ishikawa cells, in vivo: upon administration of 1 mg/kg body mass/day reduced tumor growth over 28-day period in transplanted Ishikawa cells in MF-1 nude ovariectomized mice in the presence of estradiol sulfate (prerequisite for tumor cell development in ovariectomized mice), abolished liver STS activity, and reduced plasma estradiol levels
STX213
-
highly potent, long-acting, nonestrogenic steroid sulfatase inhibitor with inhibitory properties to human carbonic anhydrase II, thus enabling transport by erythorcytes, no estrogenic effects observed in uterine weight gain study with ovariectomized Wistar rats, 24 h after last dose of 4 days of oral administration of 10 mg/kg/d, in vivo: single dose of 0.1 mg/kg 25% inhibition of liver steroid sulfatase activity, 0.5 and 1 mg/kg total inhibition, activity measured 24 h after dose administration, recovery of steroid sulfatase acitivity after single oral dose of 10 mg/kg: complete inhibition till day 4, day 12: 50% recovery, day 15: almost complete recovery
STX289
-
N,N-dimethyl 667 COUMATE, analogue of STX64, inhibition 24 h after oral application: 0.1 mg/kg inhibits liver STS by 45%, skin STS by about 39%, 1 and 10 mg/kg inhibit liver STS completely, skin STS almost completely, inhibition 24 h after topical application to neck skin: 0.1 mg/kg inhibits skin and liver STS by <50%, remote skin STS by about 10%, 1and 10 mg/kg inhibit skin STS by 98%, remote skin STS by about 80 and more than 90% respectively, and liver STS by more than 80 and close by 100% respectively
STX64
-
synonym BN83495, phenol sulfamate pharmacophore, irreversible STS inhibition from 10-1000 nM in Ishikawa cells, irreversible inhibition in OVCAR-3 ovarian cancer cells and JEG-3 choriocarcionoma cells at 10M, irreversible inhibition from 10-1000 nM in LNCaP prostate cancer cells, in vivo: upon administration of 1 mg/kg body mass/day reduced tumor growth over 28-day period in transplanted Ishikawa cells in MF-1 nude ovariectomized mice in the presence of estradiol sulfate (prerequisite for tumor cell development in ovariectomized mice), abolished liver STS activity, and reduced plasma estradiol levels
STX64
-
synonym BN83495, inhibition 24 h after oral application: 0.1 mg/kg body mass inhibits liver STS by 79%, skin STS by about 59%, 1 and 10 mg/kg inhibitis liver STS activity completely, skin STS almost completely, inhibition 24 h after topical application to neck skin: 0.1 mg/kg inhibits skin STS by 95%, remote skin STS by about 33%, liver STS by 45%, 1 and 10 mg/kg inhibits skin STS by 99%, remote skin STS almost completely, and liver STS by about 90%
STX64
-
strong STS inhibitor with phenol sulfamate pharmacophore, basis for STS inhibition in dual inhibitors in scaffold of aromatase inhibitor YM511
STX64
-
synonyms BN83495 or 667Coumate, 1 mg/kg/day given orally, treatment starting at Ishikawa cell tumor size of about 100 cubic mm (intact mice): no significant tumor growth reduction after 35 days of inhibitor treatment. Estradiol sulfate stimulated tumor growth of Ishikawa cells in ovariectomized mice, results after day 28 of inhibitor treatment: 1 mg/kg/day given orally reduces tumor growth by 48%, complete Ishikawa cell tumor STS inhibition, 1 mg/kg given orally once weekly: no tumor growth inhibition, no tumor STS inhibition, 10 mg/kg/day given orally: tumor growth inhibition by 59%, complete tumor STS inhibition
STX64
-
synonyms BN83495 or 667Coumate, estradiol sulfate stimulates tumor growth of Ishikawa cells in ovariectomized mice, results after day 28 of inhibitor treatment: 1 mg/kg/day given orally completely inhibits mouse liver STS acitivity, and reduces plasma estradiol by 63%, 1 mg/kg given orally and once weekly inhibits liver STS activity by about 40%, no plasma estradiol reduction, 10 mg/kg given orally and once weekly: complete inhibition of liver STS, and reduction of plasma estradiol by 93%
STX64
-
synonym BN83495, irreversible inhibition, STS inhibitor property within dual aromatase-sulfatase inhibitor, letrozole reversible cytochrome P450 enzyme aromatase inhibitor serves as aromatase inhibiting component
STX64
-
i.e. 667 Coumate or BN83495
sulfamic acid 2-bromo-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-bromo-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
-
dual aromatase-sulfatase inhibitor, IC50 value for aromatase 0.82 nM
sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
-
dual aromatase-sulfatase inhibitor. Alomst complete inhibition of both aromates and sulfatase in pregnant mare's serum gonadotropin pretreated female rats 3 h after a single oral dose. No inhibition of aldosterone synthesis
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethylsulfanyl)phenyl ester
-
thioether linker based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethylsulfanyl)phenyl ester
-
based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold, best dual inhibition performance in vivo in female Wistar rats: inhibition 3 h after single oral dose of 10 mg/kg body mass: 92% for aromatase, 98% for STS
sulfamic acid 2-chloro-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 3-(((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)methylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 3-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(((4-cyanophenyl)-(1,2,4)triazol-4-ylamino)methylsulfanyl)phenyl ester
-
thioether linker, , based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold, best STS inhibitor of tested dual inhibitor compounds
sulfamic acid 4-((2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)methylsulfamoyl)phenyl ester
-
N-methylated sulfonamide linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(10-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)decylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)phenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanylmethyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)-2-fluorophenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-propyl)-2-fluorophenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propylsulfanyl)phenyl ester
-
based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold, dual inhibition performance in vivo in female Wistar rats: inhibition 3 h after single oral dose of 10 mg/kg body mass: 82% for aromatase, 85% for STS
sulfamic acid 4-(5-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)pentylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 5-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]-methyl]-2-fluorophenyl ester
-
dual aromatase-sulfatase inhibitor, IC50 value for aromatase 0.77 nM
sulfamic acid 5-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]-methyl]-2-fluorophenyl ester
-
dual aromatase-sulfatase inhibitor. Potent inhibition of both aromates and sulfatase in pregnant mare's serum gonadotropin pretreated female rats 3 h after a single oral dose
Sulfate esters
-
overview, e.g. p-nitrophenyl sulfate
-
tricyclic coumarin sulfamate
-
in vitro and in vivo inhibition studies with E1-STS from different tissues, structure-activity relationship of a number of tricyclic coumarin sulfamates, the size of the third ring has a marked effect on inhibitor potency
-
TX-1299
-
non-steroid Theramex compound, strong inhibitor, IC50: 5.3 nM in JEG-3 cells, 0.76 nM in MCF-7 cells
-
TX-1299
-
non-steroid Theramex compound, potent inhibitor, in vivo inhibition study, 80% as inhibitory as 6,6,7-COUMATE
-
TX-1492
-
non-steroid Theramex compound, strong inhibitor, IC50: 22.5 nM in JEG-3 cells, 0.07 nM in MCF-7 cells
-
TX-1506
-
non-steroid Theramex compound, strong inhibitor, IC50: 11.9 nM in JEG-3 cells, 0.06 nM in MCF-7 cells
-
vanadium oxide(V)
-
50 mM, 51% residual activity
Zinc acetate
-
1.25 mM, 53% residual activity
MgCl2
-
slight
additional information
-
not inhibited by estrone, dehydroepiandrosterone, alkaline phosphatase treatment and phosphohydrolase inhibitors
-
additional information
-
not inhibited by danazol or letrozole
-
additional information
-
not inhibitory: phosphate, sulfate, sulfide
-
additional information
-
STS inhibitors were developed to treat breast cancer but could also used to treat endometriosis, polycystic ovarian disease, prostate cancer, and some androgen-dependent skin conditions, such as acne and hirsutism
-
additional information
-
not inhibited by letrozole, 5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl dimethylsulfamate, 5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl dimethylsulfamate, 5'-((1H-1,2,4-triazol-1-yl)methyl)-4-chloro-2'-cyanobiphenyl-3-yl sulfamate, 3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-3-yl sulfamate, 3'-((1H-1,2,4-triazol-1-yl)methyl)-5'-cyanobiphenyl-4-yl sulfamate, 2'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate, and 3'-((1H-1,2,4-triazol-1-yl)methyl)-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
-
additional information
-
evaluation of quinolin-2(1H)-one and quinoline derivatives of irosustat as enzyme inhibitors. N-(piperidino), N,N-(dibenzyl)sulfamate, and N,N-dimethyl derivatives of estrone 3-O-sulfamate are weak reversible or inactive inhibitors of the enzyme in placental microsomes. No inhibition by the N-benzoyl estrone 3-O-sulfamate variant 3-(benzyloxy)-8,9,10,11-tetrahydro-5H-cyclohepta[c]quinolin-6(7H)-one. Molecular modelling
-
additional information
-
design and synthesis of steroidal and nonsteroidal enzyme inhibitors as sulfamate derivatives and nonsulfamate derivatives, overview
-
additional information
-
sulfamoyloxy-substituted 2-phenylindoles are developed as antiestrogen-based inhibitors of estrone sulfatase. A series of compounds that can inhibit both aromatase and sulfatase is developed based on the structure of estrone 3-sulfamate, a typical estrone sulfatase inhibitor; synthesis and in vitro evaluation of the inhibitory potency of an extended series of 17alpha derivatives of estradiol, structure-activity relationship study, overview
-
additional information
-
inhibitor development of the enzyme in cancer treatment, clinical studies, overview
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
17beta estradiol
-
exposure to 17beta estradiol causes 9% increase of estrone 3-sulfate sulfatase activity in mammary myoepithelial cells after 6 days, but 70% reduction in MCF-7 cells
1alpha,25-dihydroxyvitamin D3
-
upregulation of enzyme activity. In HL-60 cell, stimulation is augmented by retinoid X-receptor agonists, blocked by retinoid X-receptor specific antagonists, and retinoic acid receptor specific agonists and antagonist have no effect. In NB-4 cell, upregulation is unaffected by the specific classical nuclear vitamin D receptor and retinoid X-receptor antagonists, but is blocked by a plasma-membrane associated vitamin D receptor antagonist and increases by plasma-membrane associated vitamin D receptor agonists
ascorbic acid
-
activates
Digitonin
-
activates
estrone
-
slightly activates
glutathione
-
slightly activates
glutathione
-
oxidized form, 5 mM, 187% of initial activity
Insulin
-
human recombinant insulin, 30% activation at 10 ng/ml
-
interleukin 6
-
plus tumor necrosis factor alpha, increases STS activity in mock transfected MCF-7 cells and further increases STS activity in transfected MCF-7 cells, activation occurs independently of STS promoter and enhancer elements, may activate via a post-translational modification of STS or by increasing substrate availability
interleukin-1
-
in cultured MCF-7 cells; inhibition of cell growth
-
L-beta-phenylalanine
-
5 mM, 169% of initial activity
L-cysteine
-
5 mM, 202% of initial activity
p-chloromercuribenzoate
-
activates
Triton X-100
-
activates
Tumor necrosis factor alpha
-
in cultured MCF-7 cells; inhibition of cell growth
-
Tumor necrosis factor alpha
-
plus interleucin 6, increases STS activity in mock transfected MCF-7 cells and further increases STS activity in transfected MCF-7 cells, activation occurs independently of STS promoter and enhancer elements, may activate via a post-translational modification of STS or by increasing substrate availability
-
lithocholic acid
-
5 mM, 226% of initial activity
additional information
-
not activated by 2-mercaptoethanol, cysteine or dithiothreitol
-
additional information
-
not acivating: 0.1% Triton X-100
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.02
16alpha-hydroxydehydroepiandrosterone 3-sulfate
-
-
0.217
4-methylumbelliferylsulfate
-
-
2.03
4-nitrophenyl sulfate
-
-
10
4-nitrophenyl sulfate
-
-
10.2
4-nitrophenyl sulfate
Haliotis sp.
-
-
0.00313
androstenediol 3-sulfate
-
-
0.00526
cholesterol 3-sulfate
-
-
0.0067
Cholesterol sulfate
-
pH 6.4, 37C
0.014
dehydroandrosterone 3-sulfate
-
-
0.003
dehydroepiandrosterone 3-sulfate
-
-
0.00385
dehydroepiandrosterone 3-sulfate
-
-
0.0078
dehydroepiandrosterone 3-sulfate
-
-
0.008
dehydroepiandrosterone 3-sulfate
-
-
0.00944
dehydroepiandrosterone 3-sulfate
-
37C
0.0154 - 0.0268
dehydroepiandrosterone 3-sulfate
-
in presence or absence of phosphate
0.033
dehydroepiandrosterone 3-sulfate
-
-
0.036
dehydroepiandrosterone 3-sulfate
-
pH 7.4, 50C
0.05
dehydroepiandrosterone 3-sulfate
-
-
0.113
dehydroepiandrosterone 3-sulfate
-
-
0.0017
dehydroepiandrosterone sulfate
-
-
0.0036
dehydroepiandrosterone sulfate
-
37C, MCF-7 cells
0.0043
dehydroepiandrosterone sulfate
-
pH 7.5, 37C, subcortical white matter, female
0.0044
dehydroepiandrosterone sulfate
-
pH 7.5, 37C, cerebral neocortex, male
0.0059
dehydroepiandrosterone sulfate
-
pH 7.5, 37C, cerebral neocortex, female
0.0074
dehydroepiandrosterone sulfate
-
pH 7.5, 37C, subcortical white matter, male
0.00959
dehydroepiandrosterone sulfate
-
pH 8, 37C
0.013
dehydroepiandrosterone sulfate
-
37C, mammary myoepithelial cells
0.005
esterone 3-sulfate
-
-
0.0506
esterone 3-sulfate
-
-
0.0063
Estrone 3-sulfate
-
37C, MCF-7 cells
0.035
Estrone 3-sulfate
-
37C, mammary myoepithelial cells
0.00215
Estrone sulfate
Q45FD5
37C, 10 min reaction time, Ringer-HEPES buffer, Vmax=24.05 fmol/s/microgram protein
0.00685
Estrone sulfate
-
37C
0.072
Estrone sulfate
-
pH 7.5, 37C, POGS-5 microsomes
0.07275
Estrone sulfate
-
pH 8, 37C
0.1
methylumbelliferyl sulfate
-
esterone 3-sulfate
0.27
methylumbelliferyl sulfate
-
s-form
0.45
methylumbelliferyl sulfate
-
hydropobic form
0.58
methylumbelliferyl sulfate
-
f-form
2.5
methylumbelliferyl sulfate
-
hydrophilic form
0.007
p-Nitrophenyl sulfate
-
-
1.32
p-Nitrophenyl sulfate
-
-
1.8
p-Nitrophenyl sulfate
-
-
1600
p-Nitrophenyl sulfate
-
-
1
p-nitrophenylsulfate
-
-
0.00073
pregnenolone 3-sulfate
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6.48
dehydroepiandrosterone sulfate
-
pH 8, 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0022
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)(oxo)acetic acid
-
-
0.05
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)acetic acid
-
or above
0.00025
17alpha-benzyl-17beta-hydroxyestra-1,3,5-(10)-triene-3-boronic acid
-
30C, pH 7.0
0.00025
17alpha-benzyl-3,17beta-dihydroxyestra-1,3,5-(10)-triene
-
30C, pH 7.0
0.02
2-(1-adamantyl)-4-oxo-4H-chromene-6-carbaldehyde
-
or above
0.05
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxamide
-
or above
0.0005
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylic acid
-
-
0.05
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carbonitrile
-
or above
0.00053
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carboxylic acid
-
-
0.032
2-(1-adamantyl)-6-(hydroxymethyl)-4H-chromen-4-one
-
-
0.0032
2-(1-adamantyl)-6-glycoloyl-4H-chromen-4-one
-
-
0.000085
2-formyl-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
pH 7.0, temperature not specified in the publication
0.0046
2-tert-butyl-6-hydroxy-4H-chromen-4-one
-
30C, pH 7.0
0.035
3-nitrophenyl sulfamate
-
-
0.98
3-nitrophenyl sulfamate
-
-
1.6
3-nitrophenyl sulfamate
Haliotis sp.
-
-
0.000015
667-coumate
-
37C
0.0021
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
30C, pH 7.5
0.0028
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
30C, pH 7.0
0.0038
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
30C, pH 8.0
0.0068
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
30C, pH 8.8
0.007
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
30C, pH 8.5
0.063
estrone
-
30C, pH 7.0
0.000026
KW-2581
-
37C
0.05
methyl 2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylate
-
or above
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.004633
(R)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0000032 mM
0.000553
(S)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0000143 mM
0.0026
1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000003 mM
0.0000163
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
-
-
0.000078
2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.001
2-phenylindole sulfamate
-
2-phenylindole sulfamates with lipophilic side chains in 1- or 5-position of the indole with IC50-values between 2 nM and 0.001 mM, irreversibly inhibits hydrolysis of estrone sulfate in MDA-MB 231 cells, inhibits gene activation in estrogen receptor-posi
0.086
2-t-butyl-4H-1-benzopyran-4-one-6-boronic acid
-
30C, pH 7.0
0.0000326
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
-
-
0.006333
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
-
-
0.00016
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
-
-
0.00014
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
-
-
0.0055
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
-
-
0.000032
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000001
3-sulfamoyloxy-N-(1''-pyridin-3''-ylmethyl)-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
0.000000035
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
-
in vitro JEG-3 cells: 0.001-10000 nmol/l inhibitor and incubation with estrone-3-sulfate, IC50 for human carbonic anhydrase II = 0.000003 mM
0.000001
3-sulfamoyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
0.0000286
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
0.00005
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
0.00038
4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
0.00004
4-fluoro-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
pH 7.0, temperature not specified in the publication
0.000007
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.0002
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
-
665 COUMATE, placental IC50: 200 nM
0.000035
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
0.0000055
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
0.01
5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
0.0024
5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
pH not specified in the publication, temperature not specified in the publication
0.0016
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00022
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000000015
6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000000022
6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00024
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
pH not specified in the publication, temperature not specified in the publication
0.001
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide
-
above, pH not specified in the publication, temperature not specified in the publication
0.000283
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.01
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate
-
above, in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.0000015
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.0001
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00006
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
-
6612 COUMATE, placental IC50: 60 nM
0.000000025
6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000001
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
-
6610 COUMATE, placental IC50: 1 nM
0.00003
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
-
668 COUMATE, placental IC50: 30 nM
0.0000009
6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00007
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
-
666 COUMATE, placental IC50: 70 nM
0.00037
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
0.000075
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
-
6613 COUMATE, placental IC50: 75 nM
0.000013
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
-
6611 COUMATE, placental IC50: 13 nM
0.0000024
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
-
669 COUMATE, placental IC50: 2.4 nM
0.00000043
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
IC50 0.43 nM in MCF-7 cells
0.0000051
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
6,6,7-COUMATE, IC50: 5.1 nM in JEG-3 cells
0.000008
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
667 COUMATE, placental IC50: 8 nM
0.171
6-oxo-8,9,10,11-tetrahydro-7H-cylohepta-[c][1]benzopyran-boronic acid
-
30C, pH 7.0
0.0000029
667-coumate
-
37C
0.00000008
estrone-3-sulfamate
-
IC50 0.08 nM in MCF-7 cells
0.0000032
estrone-3-sulfamate
-
best inhibitor, IC50: 3.2 nM in JEG-3 cells
0.000015
KW-2581
-
37C
0.0000015
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
-
0.00000018
STX213
-
in vitro JEG-3 cells: 0.001-10000 nmol/l inhibitor and incubation with estrone-3-sulfate, IC50 for human carbonic anhydrase II = 0.000005 mM
0.0000015
STX64
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0003 mM
0.0000015
STX64
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0003 mM
0.000008
STX64
-
placental microsomes, pH not specified in the publication, temperature not specified in the publication
0.0061
sulfamic acid 2-bromo-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.000001 mM
0.0055
sulfamic acid 2-bromo-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000015 mM
0.000039
sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
-
-
0.0015
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000017 mM
0.0012
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethylsulfanyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000045 mM
0.0015
sulfamic acid 2-chloro-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000021 mM
0.0035
sulfamic acid 3-(((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)methylsulfanyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000039 mM
0.01
sulfamic acid 3-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanyl)phenyl ester
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000017 mM
0.0009
sulfamic acid 4-(((4-cyanophenyl)-(1,2,4)triazol-4-ylamino)methylsulfanyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000055 mM, best STS inhibitor of tested dual inhibitors
0.01
sulfamic acid 4-((2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)methylsulfamoyl)phenyl ester
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00001 mM
0.0019
sulfamic acid 4-(10-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)decylsulfanyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000055 mM
0.01
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)phenyl ester
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000021 mM
0.01
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanylmethyl)phenyl ester
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000037 mM
0.0026
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)-2-fluorophenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.000002 mM
0.0016
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-propyl)-2-fluorophenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000025 mM
0.01
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000089 mM
0.01
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propylsulfanyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 larger than 0.01 mM, IC50 for aromatase = 0.00000051 mM
0.001
sulfamic acid 4-(5-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)pentylsulfanyl)phenyl ester
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000073 mM
0.00059
sulfamic acid 5-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]-methyl]-2-fluorophenyl ester
-
-
0.00000076
TX-1299
-
non-steroid Theramex compound, strong inhibitor, 0.76 nM in MCF-7 cells
-
0.0000053
TX-1299
-
non-steroid Theramex compound, strong inhibitor, IC50: 5.3 nM in JEG-3 cells
-
0.0000225
TX-1492
-
non-steroid Theramex compound, strong inhibitor, IC50: 22.5 nM in JEG-3 cells
-
0.00000006
TX-1506
-
non-steroid Theramex compound, strong inhibitor, 0.06 nM in MCF-7 cells
-
0.0000119
TX-1506
-
non-steroid Theramex compound, strong inhibitor, IC50: 11.9 nM in JEG-3 cells
-
0.00092
1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000012 mM
additional information
1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
at 10 microM 21.5% inhibition of STS activity in JEG-3 cells, IC50 for aromatase = 0.000013 mM
0.000476
1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000043 mM
additional information
1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole
-
at 10 microM 10.9% inhibition of STS activity in JEG-3 cells, 40% inhibition of aromatase
additional information
1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
at 10 microM 31.4% inhibition of STS activity in JEG-3 cells, IC50 for aromatase = 0.000099 mM
additional information
1-[bis-(4-sulfamoyloxy-3-methoxyphenyl)methyl]-1H-[1,2,4]triazole
-
at 10 microM 11.9% inhibition of STS activity in JEG-3 cells, 33% inhibition of aromatase
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000002961
-
-
0.0000128
-
pH 7.5, 37C, subcortical white matter
0.000015
-
in primary mammary carcinoma
0.0000265
-
pH 7.5, 37C, cerebral neocortex
0.385
-
pH 6.4, 37C
1.52
-
-
1.556
-
pH 8, 37C, hydrolysis of dehydroepiandrosterone sulfate
additional information
-
STS activities in male or female aortas with different degrees of atherosclerotic changes
additional information
-
-
additional information
-
higher specific activity in the dermal papilla by a factor of 6-8 than in the connective tissue sheaths or root sheaths
additional information
-
no sex- or age-specific differences in cerebral STS activity
additional information
-
-
additional information
-
STS activity in 86% of human endometrial cancer tissue, 26% in normal endometrial tissue in 26%, confirmed by immunohistochemistry, STS acitivity in MCF-7 breast cancer cells about 20 fmol/20 h/million cells, STS acitivity in Ishikawa endometrial cancer cells 39.4 fmol/20 h/million cells, STS acitivity in LNCaP prostate cancer cells 41.5 fmol/20 h/million cells, STS acitivity in OVCAR-3 ovarian cancer cells 127.4 fmol/20 h/million cells
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4
-
and pH 7.4, 2 optima
4.5
-
flat optimum
4.6
-
assay at
5 - 5.5
-
and pH 7.5, 2 optima, cholesterol 3-sulfate
5 - 5.5
-
-
6.6
-
dehydroepiandrosterone 3-sulfate
6.8
-
4-methylumbelliferyl sulfate
6.9
-
f-form
7 - 7.2
-
-
7 - 7.5
-
STS from temporal lobe
7.3 - 7.5
-
and pH 5.0, 2 optima, cholesterol 3-sulfate
7.3 - 7.5
-
-
7.3
-
p-nitrophenyl sulfate
7.4
-
and pH 4.0, 2 optima
7.4
-
assay at
7.5 - 8
-
placenta
7.5
-
assay at
7.7
-
fast form
8
-
esterone 3-sulfate
8
-
slow form
8
-
dehydroepiandrosterone 3-sulfate
8
-
esterone 3-sulfate
8
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4 - 8
-
-
5 - 8.5
-
pH 5: about 25% of activity maximum, pH 8.5: about 15% of activity maximum, dehydroepiandrosterone 3-sulfate
6 - 9
-
pH 6.0: about 20% of activity maximum, pH 9.0: about 60% of activity maximum
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
-
assay at
37
-
assay at
37
-
assay at
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 60
-
-
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.1
-
isoelectric focussing, pH-gradient 2-10
8.7
-
isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
transcription is regulated by two promoters which differ from the prevalent placental one. Specific activity of adipose tissue enzyme is about 50-100 times lower than by placenta enzyme
Manually annotated by BRENDA team
-
adult, relatively high STS activity
Manually annotated by BRENDA team
-
abdominal, STS expression levels are higher in the vascular smooth muscle cells obtained from female aortas with mild atherosclerotic changes than in those with severe atherosclerotic changes in male aortas regardless of atherosclerotic changes
Manually annotated by BRENDA team
-
plasma estradiol levels are stimulated 3 days ahead of inhibitor application with pregnant mare's serum gonadotropin (PMSG)
Manually annotated by BRENDA team
-
midbrain, hypothalamus
Manually annotated by BRENDA team
-
fetal and adult, age- and sex-dependent STS expression pattern, mature temporal lobe: about 10times lower expression than in the placenta, STS activity and expression is twice as high in cerebral neocortex than in subcortical white matter, STS is detectable in adult neurons as well as in fetal and adult Cajal-Retzius cells
Manually annotated by BRENDA team
-
analysis of enzyme activity and sulfuryl trasnferase activity in the 55 most frequent human brain tumors
Manually annotated by BRENDA team
-
fibroblasts from normal and malignant breast tissue, study of the regulation of STS mRNA expression
Manually annotated by BRENDA team
-
moderate level of enzyme immunoreactivity
Manually annotated by BRENDA team
-
expression of STS mRNA and STS activity are increased in malignant breast tissues compared with that in non-malignant tissues
Manually annotated by BRENDA team
-
hormone-dependent
Manually annotated by BRENDA team
-
reduced enzyme activity
Manually annotated by BRENDA team
-
steroid sulfatase enzyme activity is detected in the great majority of breast carcinomas
Manually annotated by BRENDA team
-
patients with endometrial carcinoma
Manually annotated by BRENDA team
-
male, highest enzymic activity in cerebellum followed by cortex and subcortex, female, highest activity in cortex followed by subcortex and cerebellum
Manually annotated by BRENDA team
-
male, highest enzymic activity in cerebellum followed by cortex and subcortex, female, highest activity in cortex followed by subcortex and cerebellum
Manually annotated by BRENDA team
-
male, highest enzymic activity in cerebellum followed by cortex and subcortex, female, highest activity in cortex followed by subcortex and cerebellum
Manually annotated by BRENDA team
-
immunohistochemistry: STS activity in 60% and 61% of patients with colon carcinoma, patients with no STS but estrogen sulfotransferase activity (-/+) have better clinical prognosis than all other activity pairs of these enzymes (+/-, +/+, -/-)
Manually annotated by BRENDA team
-
endometrial tumor, evaluation of aromatase and steryl-sulfatase activites using tritium-labeled steroids
Manually annotated by BRENDA team
-
of fallopian tubes
Manually annotated by BRENDA team
-
primary epithelial cell, highest activity of galacose 6-sulfatase and aryl sulfatase B of all the cell lines tested
Manually annotated by BRENDA team
-
from 10 patients in follicular and early luteal phases during gynecological laparotomy, epithelium, expression pattern
Manually annotated by BRENDA team
-
from normal and malignant breast tissue, study of the regulation of STS mRNA expression, expression in fibroblasts derived from breast tissue proximal to tumors, breast tumor tissue and reduction mammoplasty tissue, effect of menopausal status
Manually annotated by BRENDA team
-
luteinized, follicle
Manually annotated by BRENDA team
-
primary cultures of granulosa cells matured in vitro with follicle-stimulating hormone and testosterone
Manually annotated by BRENDA team
-
scalp biopsies, beard and occipital hair follicles ex vivo, predominantly expressed in the dermal papilla
Manually annotated by BRENDA team
-
human embryonic kidney cells
Manually annotated by BRENDA team
-
human embryonic kidney carcinoma cell line
Manually annotated by BRENDA team
-
human embryonic kidney carcinoma cell line selected for overexpression of transfected His6-tagged STS cDNA to aid purification of the His6-tagged STS protein and subsequent antibody production in mice and rabbits
Manually annotated by BRENDA team
-
acute myeloid leukaemia cell line
Manually annotated by BRENDA team
-
human endometrial adenocarcinoma cell culture, human Ishikawa cells transplanted into MF-1 ovariectomized naked mouse model
Manually annotated by BRENDA team
-
human endometrial adenocarcinoma cells transplanted into athymic MF-1 intact and ovariectomized naked mouse model
Manually annotated by BRENDA team
-
choriocarcinoma cell line
Manually annotated by BRENDA team
-
choriocarcinoma cell, more than 80times higher enzyme activity than in MCF-7 cells
Manually annotated by BRENDA team
-
choriocarcinoma cell line in monolayer
Manually annotated by BRENDA team
-
choriocarcinoma cell line used for expression test for transfection experiments
Manually annotated by BRENDA team
-
human choriocarcinoma cells
Manually annotated by BRENDA team
-
choriocarcinoma cells
Manually annotated by BRENDA team
Q45FD5
all cells with positive StS expression,exception: 65.1% StS expression in 50-day-old animal's Leydig cells
Manually annotated by BRENDA team
-
adult, relatively high STS activity
Manually annotated by BRENDA team
-
strong positive immunostaining for enzyme
Manually annotated by BRENDA team
-
liver STS activitiy
Manually annotated by BRENDA team
-
MF-1 mice with transplanted Ishikawa cells grown into tumors
Manually annotated by BRENDA team
-
human prostate cancer cells with mutated androgen receptor, as is typical for many human prostate tumors
Manually annotated by BRENDA team
-
strong positive immunostaining for enzyme
Manually annotated by BRENDA team
-
peripheral blood lymphocyte
Manually annotated by BRENDA team
-
from normal mammary tissue, slightly lower STS mRNA expression but 120times higher STS activity than in MCF-7 cells
Manually annotated by BRENDA team
-
breast cancer cell line
Manually annotated by BRENDA team
-
breast adenocarcinoma cell, more than 80times lower enzyme activity than in JEG-3 cells
Manually annotated by BRENDA team
-
breast cancer cells, study of the regulation of STS mRNA expression
Manually annotated by BRENDA team
-
derived from a metastatic malignant mammary epithelial cell line, slightly higher STS mRNA expression but 120times lower STS activity than in mammary myoepithelial cells
Manually annotated by BRENDA team
-
remarkably low activity of arylsulfatase A, arylsulfatase B, galacose 6-sulfatase and steryl sulfatase, but not iduronate 2-sulfatase
Manually annotated by BRENDA team
-
ER positive human breast cancer cells, used for transfection and activity experiments, shows STS activity by itself in contrast to monkey COS-1 cells used for the same experiments
Manually annotated by BRENDA team
-
stably transfected breast cancer cells
Manually annotated by BRENDA team
-
the MCS-2 cell line is established by introduction of the human STS gene into estrogen-dependent human breast cancer MCF-7 cells, MCS-2 cells are transplanted into female nude mice
Manually annotated by BRENDA team
-
mammary carcinoma cell line
Manually annotated by BRENDA team
-
primary myoepithelial cell, highest activity of steryl sulfatase and aryl sulfatase B of all the cell lines tested
Manually annotated by BRENDA team
-
acute myeloid leukaemia cell line
Manually annotated by BRENDA team
-
luteinized granulosa cells
Manually annotated by BRENDA team
-
crude homogenate, from immature female Sprague-Dawley rats treated with gonadotropin in vivo
Manually annotated by BRENDA team
-
human ovarian cancer cell line
Manually annotated by BRENDA team
-
about 10times higher expression than in the temporal lobe
Manually annotated by BRENDA team
-
adult, highest STS activity
Manually annotated by BRENDA team
-
microsomes, at least two distinct forms of CHS-ase
Manually annotated by BRENDA team
-
specific activity of adipose tissue enzyme is about 50-100 times lower than by placenta enzyme
Manually annotated by BRENDA team
-
strong positive immunostaining for enzyme
Manually annotated by BRENDA team
-
MF-1 mice with transplanted Ishikawa cells grown into tumors
Manually annotated by BRENDA team
-
immortalized rat granulosa cell line
Manually annotated by BRENDA team
-
gene expression of both sulfotransferase and steroid sulfatase in all prostate cancer cell lines examined, accompanied by synthesis of estrone and estradiol. 85% of cell lines show immunoreactivity for steroid sulfatase
Manually annotated by BRENDA team
-
cultured fibroblasts
Manually annotated by BRENDA team
-
strong positive immunostaining for enzyme
Manually annotated by BRENDA team
-
remarkably low activity of arylsulfatase A, arylsulfatase B, galacose 6-sulfatase and steryl sulfatase, but not iduronate 2-sulfatase
Manually annotated by BRENDA team
-
human female vascular smooth muscle cell line
Manually annotated by BRENDA team
-
1-3.7% of the mRNA levels of placenta, adult
Manually annotated by BRENDA team
-
STS expression levels are higher in the vascular smooth muscle cells obtained from female aortas with mild atherosclerotic changes than in those with severe atherosclerotic changes in male aortas regardless of atherosclerotic changes
Manually annotated by BRENDA team
additional information
-
distribution of STS mRNA in human adult and fetal tissues
Manually annotated by BRENDA team
additional information
-
enzyme staining and mRNA expression changes with the menstrual cycle
Manually annotated by BRENDA team
additional information
-
no STS activity in the immortalized rat granulosa cell line POGRS-1
Manually annotated by BRENDA team
additional information
-
not in endothelial cells or inflammatory cells including macrophages
Manually annotated by BRENDA team
additional information
-
STS expression pattern
Manually annotated by BRENDA team
additional information
-
analysis of gene transcription in ten different tissues. Enzyme expression is driven by six different promoters giving rise to transcripts with unique first exons. Whatever ATG is actually used, the differences on protein level are restricted to the signal peptide which is post-transcriptionally cleaved
Manually annotated by BRENDA team
additional information
-
distinct expression patterns of enzyme in different tissues, due to at least four alternatively spliced transcripts. Estrogen receptor alpha is an essential regulator of transcription
Manually annotated by BRENDA team
additional information
-
ER+/ER+ breast cancer cells show strong leveles of enzyme immunoreactivity, ER-/ER- breast cancer cells show weak immunoreactivity
Manually annotated by BRENDA team
additional information
-
enzyme activity is reduced in menopausal women
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
of epithelial cells from fallopian tubes
Manually annotated by BRENDA team
-
low enzymic activity
Manually annotated by BRENDA team
-
bound to the membrane of the endoplasmic reticulum
Manually annotated by BRENDA team
-
STS activity is enriched in the membrane fraction of the temporal lobe
Manually annotated by BRENDA team
-
membrane-bound
-
Manually annotated by BRENDA team
-
membrane-bound
-
Manually annotated by BRENDA team
-
from POGS-5 cell line
-
Manually annotated by BRENDA team
-
placental, at least two distinct forms of CHS-ase
-
Manually annotated by BRENDA team
-
STS is a membrane-bound microsomal enzyme
-
Manually annotated by BRENDA team
additional information
-
subcellular distribution of STS in the temporal lobe
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
22900 - 174000
-
series of isoenzymes
135595
44000
-
-
135595
54000
-
amino acid analysis
135605
60000
-
SDS-PAGE
135618
60000
-
linkage of the murine STS locus to the pseudoautosomal region in the X and Y chromosome
135627
61000
-
SDS-PAGE, immunoblot analysis with specific antibody
694168
62000
-
SDS-PAGE
135599
62000
-
-
135601
62000
-
SDS-PAGE
135618
62000
-
amino acid analysis
135622
64000
-
placenta, reduced, SDS-PAGE
135602
73000
-
placenta, SDS-PAGE
135616
74000
-
gel filtration
681650
103000 - 105000
-
brain
135595
128000
-
gel filtration
135618
130000
-
estrone sulfatase is identical to arylsulfatase C but not to sulfatases which hydrolyse dehydroepiabdrosterone, testosterone, pregnenolone, and cholesterol; gel filtration
135613
150000
-
-
135595
180000
-
gel filtration, in the presence of Triton X-100
656637
183000
-
placenta, s-form, gel filtration, two isoforms s- and f-form
135615
200000
-
liver, f-form, gel filtration, two isoforms s- and f-form
135615
238000
-
gel filtration
135604
250000
-
gel filtration
656641
270000
-
placenta, nonreduced, gel filtration
135602
270000
-
gel filtration
135611, 135612
280000
-
gel filtration
135595, 135607
390000
-
placenta, gel filtration
135611
440000
-
placenta
135595
500000 - 600000
-
placenta, gel filtration
135616
additional information
-
native PAGE analysis of solubilized single crystals of ES shows all possible oligomeric states between a monomer and a tetramer, but predominantly the monomeric and dimeric states
656641
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 62000, SDS-PAGE
?
-
x * 65000, SDS-PAGE
?
-
x * 30000, SDS-PAGE
?
-
x * 64000, SDS-PAGE of enzymes from placenta and adipose tissue
dimer
-
coprecipitation of mutant enzyme with FLAG-tagged enzyme
heterotetramer
-
alpha2,beta2, 2 * 57000 + 2 * 38000, two 57 kDa catalytic and two 38 kDa regulatory subunits, SDS-PAGE
hexamer
-
6 * 74000, placenta, SDS-PAGE
tetramer
-
4 * 72000, SDS-PAGE
trimer
-
alpha, 3 * 78000, SDS-PAGE,solubilized in Triton X-100
monomer
-
1 * 78000, solubilized in Triton X-100
additional information
-
all oligomeric states between a monomer and a tetramer are possible, varying aggregation properties of enzyme under various buffer, pH, detergent and ionic strength conditions, gel filtration suggests ES to be predominantly a homotetramer, native PAGE analysis of solubilized single crystals of ES shows all possible oligomeric states between a monomer and a tetramer, but predominantly the monomeric and dimeric states
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
-
is glycosylated, binds to concanavalin A
glycoprotein
-
-
glycoprotein
-
enzyme synthesized as a membrane-bound polypeptide with asparagine linked oligosaccharide chains, processing of oligosaccharide chains within 2 days
glycoprotein
-
3 sites for possible glycosylation
glycoprotein
-
rich in mannose and N-acetylglucosamine
glycoprotein
-
high mannose-type
glycoprotein
-
4 sites for possible glycosylation, only 2 sites used
glycoprotein
-
contains sialic acid
glycoprotein
-
asparagine-linked oligosaccharide chains
glycoprotein
-
N-linked glycosylation at two of the possible four sites
glycoprotein
-
4 potential glycosylation sites
proteolytic modification
-
enzyme expression is driven by six different promoters giving rise to transcripts with unique first exons. Whatever ATG is actually used, the differences on protein level are restricted to the signal peptide which is post-transcriptionally cleaved
glycoprotein
-
rich in mannose and N-acetylglucosamine
glycoprotein
-
high mannose-type
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis of placenta microsome enzyme, overview
-
full-length, active enzyme form, X-ray analysis
-
in complex with inhibitor sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
-
5 h, 20% loss of activity
135604
50
-
3 h, 50% loss of activity
135604
50
-
f-form: 50% loss of activity
135615
55
-
t1/2: 11 min
135595
57
-
s-form: 50% loss of activity
135615
60
-
10 min, 50% loss of activity
135600
60
-
30% loss of activity
135621
60
-
5 min, 40% loss of activity
656643
60
-
5 min, 115% resiudal activity
681650
70
-
10 min, 50% loss of activity
135613
70
-
complete loss of activity
135621
80
-
5 min, 100% residual activity
681650
100
-
5 min, 87% residual activity
681650
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
lyophilization, deactivation
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
room temperature, crystalline state of enzyme, more than 30 days, less than 33% loss of specific activity
-
room temperature, n-octyl-beta-D-glucopyranoside, several weeks, nearly stable
-
-20oC, pH 8, 0.3% Triton X-100, several months, no loss of activity
-
4oC, pH 7.4, imidazol buffer, several months, small loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
99.3fold
-
partial
-
partial, the soluble enzyme
-
affinity chromatography with NiCl2-primed HisTrap Chelating columns and concentrated 6-fold using ICON concentrators
-
enzyme does not copurify with oestrone sulfate sulfohydrolase
-
of the recombinant protein
-
solubilized with 0.5% Triton X-100, two fractions with cholesterol sulfate sulfohydrolase activity are separated by DEAE-cellulose chromatography, purification of the 30 kDa enzyme
-
partial
-
to homogeneity
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2.4 kb STS cDNA, expression in MCF-7 and COS-1 cells
-
expression in Escherichia coli and CHO cells
-
expression in monkey kidney COS-1 cells
-
expression in mouse A9 cells
-
His6-tagged wild-type STS cDNA subcloned into pCEP4, transfected into 293-EBNA cells, cell line with stable overexpression of STS-His6 selected for production of tagged wildtype STS, subsequent specific antibody production, mutated STS is transfected into human MCF-7 cells and monkey COS-1 cells to test for STS activity by immunoblotting
-
overexpression of STS gene in human breast cancer MCF-7 cells, i.e. MCS-2 cells, transplanted in female nude mice
-
partial sequence of porcine StS, subcloned into pGEM T vector, amplified in Escherichia coli
Q45FD5
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
shikonin, an ingredient of Lithospermum erythrorhizon, down-regulates the expression and activity of steroid sulfatase in breast cancer cells
-
Shu-Gan-Liang-Xue decoction down-regulates the expression of steroid sulfatase genes in human breast carcinoma MCF-7 cells in a dose-dependent manner
-
trichostatin A treatment suppresses STS mRNA expression
-
steroid sulfatase expression is upregulated in breast carcinomas
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C446Y
-
patient with X-linked ichthyosis
DELTA1-21
-
lacks 21 N-terminal amino acids, that encode the signal peptide, reduced STS activity
DELTA185-583
-
lacks 399 C-terminal amino acids, reduced STS activity
H136F
-
point mutation in histidine 136, reduced STS activitiy
H136W
-
point mutation in histidine 136, reduced STS activity
H136Y
-
point mutation in histidine 136, reduced STS activity
N259Q
-
point mutation in asparagine 259 glycosylation site, reduced STS activity
N333Q
-
point mutation in other potential glycosylation site asparagine 333, no reduced STS activity
N459Q
-
point mutation in other potential glycosylation site asparagine 459, no reduced STS activity
N47Q
-
point mutation in asparagine 47 glycosylation site, reduced STS activity
N47Q/N259Q
-
double mutation in asparagine 47 and 259 glycosylation sites, reduced STS activity
N54Q
-
point mutation in in asparagine 54 non-glycosylation site , no reduced STS activity
P212G
-
point mutation in proline 212, no reduced STS activity
Q560P
-
no effect of mutation on enzyme synthesis and degradation, dominant negative effect on enzyme activity when coexisting with wild-type enzyme
R419S
-
patient with X-linked ichthyosis
S341L
-
patient with X-linked ichthyosis
W372P
-
patient with X-linked ichthyosis
W372R
-
patient with X-linked ichthyosis
H444R
-
patient with X-linked ichthyosis
additional information
-
c-terminal truncation mutant using codons 1-559, no effects on protein synthesis and degradation, dominant negative effect on enzyme activity when coexisting with wild-type enzyme
additional information
-
site directed mutagenisis is introduced using pALTERMax kit
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
-
method for the evaluation of aromatase and steryl-sulfatase activites in endometrial tumors using tritium-labeled steroids
medicine
-
-
medicine
-
increased activity in endocrine-dependent tumors
medicine
-
higher activity in primary mammary carcinoma
medicine
-
steryl-sulfatase deficient placenta has lower aromatase activity
medicine
-
also associated with multiple sulfatase deficiency
medicine
-
point mutations in 3 patients
medicine
-
deficiency in X-linked placental insufficiency and X-linked ichthyosis
medicine
-
2-phenylindole sulfamates with antiproliferative activity in breast cancer cells are devoid of estrogenic activity and have the potential for in vivo application as steroid sulfatase inhibitors in the treatment of hormone-dependent breast cancer
medicine
-
blocking of dehydroepiandrosterone sulfate sulfatase activity could be prove to be clinically important in oestrogen-dependent tumors in pre-menopausal women
medicine
-
estrone sulfatase inhibitors can be used as drugs for the treatment of estrogen-dependent breast cancer
medicine
-
the expression of STS is an independent prognostic factor in breast cancer, STS is a new molecular target for the treatment of estrogen-dependent breast tumor post-selective estrogen receptor modulator and/or aromatase inhibitors
medicine
-
X-linked ichthyosis is ascribed to the non-functional ES resulting from point and/or deletion mutations in the ES gene
medicine
-
expression level of enzyme mRNA is significantly higher cumulus cells from patients with endometriosis than in control cumulus cells
medicine
-
No significant correlation among the expression of enzymes involved in intratumoral estrogen expression in endometrial carcinoma tissue. No significant differences between steroid sulfatase, estrogen sulfotransfarase and estrogen receptor, progesterone receptor, Ki67, histologic grade, or clinical outcomes of the patients
medicine
-
study on the effect of N-and C-terminal trucated enzyme mimicking enzyme deficiency in X-linked ichthyosis
medicine
-
analysis of enzyme activity and sulfuryl transferase activity in the 55 most frequent human brain tumors incuding glioblastomas, pituitatry adenomas, meningiomas, astrocytomas. Significant differences in enzyme activity among the investigated types of tumors, that do not depend on sex or age of subjects
medicine
-
benzothiophene sulfates of raloxifene and arzoxifene used as hormone replacement therapeutic agents are hydrolyzed by the enzyme, whereas the raloxifene 4'-phenolic sulfate is resistant. Tissue specific expression of sulfotransferase isoforms and of steroid sulfatase can be important in the inactivation and regeneration of the active form of hormone replacement therapeutic agents
medicine
-
method for the evaluation of aromatase and steryl-sulfatase activites in endometrial tumors using tritium-labeled steroids
medicine
-
remarkably different expression of enzyme isoforms in estrogen receptor alpha-positive and -negative breast carcinomas. Estrogen receptor alpha is an essential regulator of transcription
medicine
-
treatment of postmenopausal women with estrogen receptor-positie metastatic breast cancer using inhibitor 6-oxo-7,8,9,10,11,12-hexahydro-6H-cycloocta[c]chromen-3-yl sulfamate, i.e. STW64. Inhibitor almost completely blocks enzyme activty in peripheral blood lymphocytes and tumor tissues, inhibition is associated with significant reductions in serum concentrations of androstenediol and estrogens. Serum androstenedione concentration also decreases by up to 86%. Of eight patients that completed therapy, five show evidence of stable disease for up to 7 months
medicine
-
patients with no STS but estrogen sulfotransferase activity (-/+) have better clinical prognosis than all other activity pairs of these enzymes (+/-, +/+, -/-)
pharmacology
-
enzyme inhibitors can be used as anti-tumor agents
pharmacology
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steroid sulfatase inhibitors could be novel drugs to treat androgen-dependent disorders of the hair follicle such as androgenetic alopecia or hirsutism
pharmacology
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the non-estrogenic STS inhibitor (p-O-sulfamoyl)-N-tetradecanoyl tyramine has anti-cancer activity and should be a potent therapeutic agent for treatment of estrogen-dependent breast cancer
medicine
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the STS inhibitors 3-sulfamoyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-16,17-imide and 3-sulfamoyloxy-N-(1-pyridin-3-ylmethyl)-16,17-seco-estra-1,3,5(10)-triene-16,17-imide are devoid of estrogenic activity and have therapeutic potential for the treatment of hormone-dependent breast cancer
medicine
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administration of oestrone sulfamate to ovariectomised animal results in 3.5fold increase in the uterine weight. Coadministation of oestrone sulfamate and 667 COUMATE completely blocks enzyme activity and completely abrogates the ability of oestrone sulfamate to stimulate uterine growth
pharmacology
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inhibition of STS is an important target for the development of new drugs for oncology and immunology
medicine
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estrone sulfatase is a target enzyme in the treatment of hormone-dependent breast cancer
additional information
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gene expression of both sulfotransferase and steroid sulfatase in all prostate cancer cell lines examined, accompanied by synthesis of estrone and estradiol. 85% of cell lines show immunoreactivity for steroid sulfatase