Literature summary for 3.1.6.2 extracted from

Wood, P.M.; Woo, L.W.; Labrosse, J.R.; Trusselle, M.N.; Abbate, S.; Longhi, G.; Castiglioni, E.; Lebon, F.; Purohit, A.; Reed, M.J.; Potter, B.V.
Chiral aromatase and dual aromatase-steroid sulfatase inhibitors from the letrozole template: synthesis, absolute configuration, and in vitro activity (2008), J. Med. Chem., 51, 4226-4238.

Search for more literature for 3.1.6.2

Inhibitors

Inhibitors	Comment	Organism	Structure
(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	Homo sapiens
(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	Homo sapiens
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	Homo sapiens
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	Homo sapiens
1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole	increase of aromatase inhibitory activity due to presence of a para-cyanophenyl moiety	Homo sapiens
1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole	best dual inhibition	Homo sapiens
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	Homo sapiens
1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole	sulfamate in meta-position increases aromatase inhibition strength compared to para-position	Homo sapiens
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	Homo sapiens
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	Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
dehydroepiandrosterone sulfate + H2O	Homo sapiens	-	dehydroepiandrosterone + sulfate	subsequent conversion to androst-5-ene-3beta,17beta-diol, an androgen with estrogenic properties, stimulating breast cancer growth	?
estrone sulfate + H2O	Homo sapiens	-	estrone + sulfate	in breast cancer tissue 10 times more estrone originates from estrone sulfate than from androstenedione	?

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	P08842	-	-

Source Tissue

Source Tissue	Comment	Organism	Textmining
JEG-3 cell	choriocarcinoma cell line in monolayer	Homo sapiens	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
dehydroepiandrosterone sulfate + H2O	-	Homo sapiens	dehydroepiandrosterone + sulfate	subsequent conversion to androst-5-ene-3beta,17beta-diol, an androgen with estrogenic properties, stimulating breast cancer growth	?
estrone sulfate + H2O	-	Homo sapiens	estrone + sulfate	in breast cancer tissue 10 times more estrone originates from estrone sulfate than from androstenedione	?

Synonyms

Synonyms	Comment	Organism
steroid sulfatase	-	Homo sapiens
STS	-	Homo sapiens

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
additional information	-	at 10 microM 10.9% inhibition of STS activity in JEG-3 cells, 40% inhibition of aromatase	Homo sapiens	1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole
additional information	-	at 10 microM 11.9% inhibition of STS activity in JEG-3 cells, 33% inhibition of aromatase	Homo sapiens	1-[bis-(4-sulfamoyloxy-3-methoxyphenyl)methyl]-1H-[1,2,4]triazole
additional information	-	at 10 microM 21.5% inhibition of STS activity in JEG-3 cells, IC50 for aromatase = 0.000013 mM	Homo sapiens	1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
additional information	-	at 10 microM 31.4% inhibition of STS activity in JEG-3 cells, IC50 for aromatase = 0.000099 mM	Homo sapiens	1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
0.0000015	-	enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0003 mM	Homo sapiens	STX64
0.000476	-	enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000043 mM	Homo sapiens	1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
0.000553	-	enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0000143 mM	Homo sapiens	(S)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
0.00092	-	enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000012 mM	Homo sapiens	1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
0.0026	-	enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000003 mM	Homo sapiens	1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
0.004633	-	enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0000032 mM	Homo sapiens	(R)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole

Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.

Release 2023.1 (January 2023)