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Information on EC 1.14.99.1 - prostaglandin-endoperoxide synthase
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1.14.99.1 prostaglandin-endoperoxide synthaseIUBMB Comments
This enzyme acts both as a dioxygenase and as a peroxidase.
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Word Map
- 1.14.99.1
- indomethacin
-
arachidonic
- cytokine
-
nsaid
- necrosis
- tnf
- endothelial
- lipopolysaccharide
-
thromboxane
- artery
-
nonsteroidal
- celecoxib
- aspirin
- pain
- lps
- lipoxygenase
- platelet
-
lps-induced
- cardiovascular
- carcinogenesis
- agonist
- gastrointestinal
- phospholipase
-
prostanoids
-
leukotriene
-
eicosanoids
- gastric
- mapks
- arthritis
- angiogenesis
- nf-kappab
- prostacyclin
-
analgesic
- colorectal
- ulcer
- tnf-alpha
-
lps-stimulated
- ibuprofen
-
vasodilator
- edema
-
nonselective
-
chemopreventive
- osteoarthritis
- il-1beta
-
l-name
-
lipopolysaccharide-induced
-
endothelium-dependent
- factor-kappab
-
vasoconstriction
-
endothelium-derived
- medicine
The enzyme appears in viruses and cellular organisms
Synonyms
cox-2, cyclooxygenase, cyclooxygenase-2, cox-1, cyclooxygenase 2, pghs-2, ptgs2, cyclooxygenase-1, prostaglandin synthetase, pghs-1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
COX
COX-1
COX-2
cyclooxygenase
cyclooxygenase 2
cyclooxygenase-1b
cyclooxygenase-2
hPGHS-2
PGHS
PGHS-1
PGHS-2
PHS
PHS-1
prostaglandin endoperoxide H synthase
prostaglandin endoperoxide H synthase-1
prostaglandin endoperoxide synthase 2
prostaglandin endoperoxide synthase-1
prostaglandin endoperoxide synthase-2
prostaglandin G/H synthase
prostaglandin H synthase
prostaglandin H synthase-1
prostaglandin H synthase-2
prostaglandin H2 synthase
prostaglandin-endoperoxide synthase
prostaglandin-endoperoxide synthase 1
prostaglandin-endoperoxide synthase 2
prostaglandin-H-synthase
PTGS1
PTGS2
PGHS-1
one of two isoforms found in mammalian cells, always present and provides their normal functioning
PGHS-2
one of two isoforms found in mammalian cells, produced in response to certain stimuli, such as cytokines and growth factors
PHS-1
PHS is a dual-function enzyme, having a cyclooxygenase and a hydroperoxidase component
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
arachidonate + reduced acceptor + 2 O2 = prostaglandin H2 + acceptor + H2O
mechanism, enzyme acts both as dioxygenase and as peroxidase
-
arachidonate + reduced acceptor + 2 O2 = prostaglandin H2 + acceptor + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
reduction
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SYSTEMATIC NAME
IUBMB Comments
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate,hydrogen-donor:oxygen oxidoreductase
This enzyme acts both as a dioxygenase and as a peroxidase.
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CAS REGISTRY NUMBER
COMMENTARY
39391-18-9
-
9055-65-6
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid + AH2 + O2
? + A + H2O
substrate binding structure and nonproductive conformation, overview
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin G2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
arachidonic acid + 2 O2
prostaglandin G2
cyclooxygenase reaction, arachidonic acid as electron donor
-
?
arachidonic acid + 3,4-methylenedioxyamphetamine
?
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
?
arachidonic acid + 3,4-methylenedioxymethamphetamine
?
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
?
arachidonic acid + AH2 + 2 O2
15-hydroperoxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid + A + H2O
-
-
-
?
arachidonic acid + AH2 + 2 O2
6-keto-prostaglandin F1alpha + A + H2O
-
activity assay
-
?
arachidonic acid + methamphetamine
?
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
?
arachidonic acid + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
r
H2O2 + N,N,N',N'-tetramethyl-p-phenylenediamine
?
-
peroxidase activity
-
?
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
the substrate is bound in the cyclooxygenase channel of COX-2, binding structure, overview. The carboxylate of docosahexaenoate interacts with Arg120 and Tyr355 at the base of the channel and the omega-end abuts the side chain of Ile377 near Gly533 in the hydrophobic groove above Ser530
-
?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
-
-
?
8,11,14-eicosatrienoic acid + O2
prostaglandin G1 + ?
-
bis-dioxygenase activity, cyclooxygenase activity, presence of hematin
9alpha,11alpha-epidioxy-15(S)-hydroperoxy-13-trans-prostenoic acid
?
8,11,14-eicosatrienoic acid + O2
prostaglandin H1 + ?
-
hydroperoxidase activity, presence of hematin and tryptophan
-
?
arachidonate + AH2 + 2 O2
prostaglandin G2 + A + H2O
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin H2 + A + H2O
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
the reaction comprises two steps: dioxygenation of arachidonate to yield prostaglandin G2 containing both a 9-11 endoperoxide and a 15-peroxide group, and a peroxidase reaction, which converts prostaglandin G2 to prostaglandin H2 where the 15-peroxide is reduced to an alcohol
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
substrate binding structure and nonproductive conformation, overview
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
the reaction comprises two steps: dioxygenation of arachidonate to yield prostaglandin G2 containing both a 9-11 endoperoxide and a 15-peroxide group, and a peroxidase reaction, which converts prostaglandin G2 to prostaglandin H2 where the 15-peroxide is reduced to an alcohol
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
cyclooxygenase activity
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
?
arachidonic acid + AH2 + 2 O2
15(R)-hydroxy-eicosatetraenoic acid + A + H2O
-
-
product of aspirin acetylated enzyme or S516M mutant
?
arachidonic acid + AH2 + 2 O2
15(R)-hydroxy-eicosatetraenoic acid + A + H2O
-
-
product of aspirin treated enzyme
?
cis-5,8,11,14,17-eicosapentaenoic acid + reduced acceptor + O2
?
-
-
r
cis-7,10,13,16-docosatetraenoic acid + reduced acceptor + O2
?
-
-
r
cis-8,11,14-eicosatrienoic acid + reduced acceptor + O2
?
-
-
r
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
-
-
?
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
-
-
?
additional information
?
-
-
major products of arachidonic acids are prostaglandins D2 and E2, minor products prostaglandin F2alpha and 6-keto-prostaglandin F1alpha
-
?
additional information
?
-
-
dopamine precursor L-dihydroxyphenylalanine, i.e. L-DOPA, and metabolites dihydroxyphenylacetic acid, homovanillic acid, and 3-methoxytyramine may serve as substrates for prostaglandin H synthase-catalyzed bioactivation to free radical intermediates
-
?
additional information
?
-
activity with arachidonate in presence of glutathione leads to formation of malondialdehyde and (15S)-8-iso-prostaglandin F2alpha
-
?
additional information
?
-
activity with arachidonate in presence of glutathione leads to formation of malondialdehyde and (15S)-8-iso-prostaglandin F2alpha
-
?
additional information
?
-
PGHS-1 also exhibits peroxidase activity
-
?
additional information
?
-
PGHS-1 also exhibits peroxidase activity
-
?
additional information
?
-
PGHS-2 also exhibits peroxidase activity
-
?
additional information
?
-
PGHS-2 also exhibits peroxidase activity
-
?
additional information
?
-
-
relative activities of isozymes 1,2 depend on source of arachidonic acid - exogenous versus endogenous
-
?
additional information
?
-
although arachidonic acid is the preferred substrate, other fatty acids are oxygenated by the isozymes with varying efficiencies. The substrates bind in different conformations in each monomer constituting the homodimer in their respective structures such that one monomer exhibits nonproductive binding and the other productive binding of the substrate in the cyclooxygenase channel, Arg120 and Leu531 play a role, overview
-
?
additional information
?
-
-
although arachidonic acid is the preferred substrate, other fatty acids are oxygenated by the isozymes with varying efficiencies. The substrates bind in different conformations in each monomer constituting the homodimer in their respective structures such that one monomer exhibits nonproductive binding and the other productive binding of the substrate in the cyclooxygenase channel, Arg120 and Leu531 play a role, overview
-
?
additional information
?
-
-
electron donors used by hydroperoxidase: phenylbutazone, sulindac
-
?
additional information
?
-
-
formation of prostaglandin E2, prostaglandin F2alpha and prostaglandin D2 from arachidonic acid
-
?
additional information
?
-
-
electron donors used by hydroperoxidase: phenylbutazone, sulindac
-
?
additional information
?
-
-
electron donors used by hydroperoxidase: phenylbutazone, sulindac
-
?
additional information
?
-
-
xenobiotics such as benzo(a)pyrene cannot act as electron donor, but undergo cooxydation during hydroperoxidase reaction
-
?
additional information
?
-
-
functional differentiation of cyclooxygenase and peroxidase activities by trypsin treatment
-
?
additional information
?
-
-
cooxidation of: 4-chloroaniline to yield N-(4-chlorophenyl)-hydroxylamine and 1-chloro-4-nitrosobenzene
-
?
additional information
?
-
-
also catalyzed: transformation of arachidonic acid into prostaglandin E2, prostaglandin F2 alpha and 12-hydroxy-5,8,10-heptadecatrienoic acid
-
?
additional information
?
-
-
enzyme has a central position in prostanoic metabolism: first step in formation of prostaglandins and thromboxanes, the conversion of arachidonic acid to prostaglandin endoperoxides G and H
-
?
additional information
?
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
?
additional information
?
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
?
additional information
?
-
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
?
additional information
?
-
-
maximal values of the initial reaction rate and yield of the product are attained at oxygen concentration 0.05 mM
-
?
additional information
?
-
-
the expression of PGHS-2 may be involved in inhibiting progesterone production
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
arachidonate + AH2 + 2 O2
prostaglandin G2 + A + H2O
-
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin H2 + A + H2O
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
?
additional information
?
-
-
dopamine precursor L-dihydroxyphenylalanine, i.e. L-DOPA, and metabolites dihydroxyphenylacetic acid, homovanillic acid, and 3-methoxytyramine may serve as substrates for prostaglandin H synthase-catalyzed bioactivation to free radical intermediates
-
-
?
additional information
?
-
activity with arachidonate in presence of glutathione leads to formation of malondialdehyde and (15S)-8-iso-prostaglandin F2alpha
-
-
?
additional information
?
-
activity with arachidonate in presence of glutathione leads to formation of malondialdehyde and (15S)-8-iso-prostaglandin F2alpha
-
-
?
additional information
?
-
-
enzyme has a central position in prostanoic metabolism: first step in formation of prostaglandins and thromboxanes, the conversion of arachidonic acid to prostaglandin endoperoxides G and H
-
-
?
additional information
?
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
-
?
additional information
?
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
-
?
additional information
?
-
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
-
?
additional information
?
-
-
the expression of PGHS-2 may be involved in inhibiting progesterone production
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
iron-protoporphyrin IX
each subunit contains a molecule of Fe3+-protoporphyrin IX noncovalently attached to the enzyme, the heme group is essential for both enzyme activities
heme
-
either free or protein-bound heme is required for cyclooxygenase- and hydroperoxidase activity
heme
ferric heme, heme content of the purified recombinant GvPGHS determined by a pyridine-hemochromogen assay is 0.39 mol of heme/mol of GvPGHS monomer
additional information
epinephrine-hydrogentartrate can serve as cofactor
-
additional information
epinephrine-hydrogentartrate can serve as cofactor
-
additional information
epinephrine-hydrogentartrate can servve as cofactor
-
additional information
epinephrine-hydrogentartrate can servve as cofactor
-
additional information
peroxidase activity of PGHS requires reducing co-substrates as electron donors
-
additional information
peroxidase activity of PGHS requires reducing co-substrates as electron donors
-
additional information
-
peroxidase activity of PGHS requires reducing co-substrates as electron donors
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe3+
Iron
Mn3+
-
substitution of ferric heme by MnIII protoporphyrin IX greatly diminishes the peroxidase activity, but has little effect on the cyclooxygenase activity
Iron
each subunit contains a molecule of Fe3+-protoporphyrin IX noncovalently attached to the enzyme, the heme group is essential for both enzyme activities, the cofactor is released by induction of inhibitor nitroarachidonic acid
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-Mercapto-9,11,15-trihydroxyprosta-5,13-diene
-
inhibition of prostaglandin G1 synthesis
1-Mercapto-9-oxo-11,15-dihydroxyprosta-5,13-dione
-
inhibition of prostaglandin G1 synthesis
12-nitroarachidonic acid
nitro-fatty acid inhibition is due to a slow, tightly binding mechanism, it inhibits oxygenase and peroxidase activity PGHS-1, kinetics, overview. Inactivation of PGHS by nitroarachidonic acid involves two sequential steps: an initial reversible binding event, followed by a practically irreversible event leading to an inactivated enzyme. Inactivation is associated with irreversible disruption of heme binding to the protein, the inhibitor induces heme release from Fe2+-protoporphyrin-PGHS-1. In activated human platelets, nitroarachidonic acid significantly decreases PGHS-1-dependent thromboxane B2 formation in parallel with a decrease in platelet aggregation
14-nitroarachidonic acid
nitro-fatty acid inhibition is due to a slow, tightly binding mechanism, it inhibits oxygenase and peroxidase activity PGHS-1, kinetics, overview. Inactivation of PGHS by nitroarachidonic acid involves two sequential steps: an initial reversible binding event, followed by a practically irreversible event leading to an inactivated enzyme. Inactivation is associated with irreversible disruption of heme binding to the protein, the inhibitor induces heme release from Fe2+-protoporphyrin-PGHS-1. In activated human platelets, nitroarachidonic acid significantly decreases PGHS-1-dependent thromboxane B2 formation in parallel with a decrease in platelet aggregation
15-nitroarachidonic acid
nitro-fatty acid inhibition is due to a slow, tightly binding mechanism, it inhibits oxygenase and peroxidase activity PGHS-1, kinetics, overview. Inactivation of PGHS by nitroarachidonic acid involves two sequential steps: an initial reversible binding event, followed by a practically irreversible event leading to an inactivated enzyme. Inactivation is associated with irreversible disruption of heme binding to the protein, the inhibitor induces heme release from Fe2+-protoporphyrin-PGHS-1. In activated human platelets, nitroarachidonic acid significantly decreases PGHS-1-dependent thromboxane B2 formation in parallel with a decrease in platelet aggregation
6-methoxy-2-naphthyl acetic acid
-
active metabolite of nabumetone, isozyme 1, 50% inhibition at 0.2-0.8 mM, isozyme 2, 50% inhibition at 0.015-0.55 mM
6-methylnaphthylacetic acid
-
recombinant protein, 50% inhibition at 0.08-0.1 mM
6-[2,4-difluorophenoxy]-5-methyl-sulfonylamino-1-indanone
-
CGP28238, an isozyme-2 specific inhibitor, 65% inhibition at 100 nM
9,11-Dihydroxy-15S-mercaptoprosta-5,13-dienoic acid
-
or 15R-isomer, inhibition of prostaglandin G1 synthesis
9-nitroarachidonic acid
nitro-fatty acid inhibition is due to a slow, tightly binding mechanism, it inhibits oxygenase activity and peroxidase activity of PGHS-1, kinetics, overview. Inactivation of PGHS by nitroarachidonic acid involves two sequential steps: an initial reversible binding event, followed by a practically irreversible event leading to an inactivated enzyme. Inactivation is associated with irreversible disruption of heme binding to the protein, the inhibitor induces heme release from Fe2+-protoporphyrin-PGHS-1. In activated human platelets, nitroarachidonic acid significantly decreases PGHS-1-dependent thromboxane B2 formation in parallel with a decrease in platelet aggregation
anirolac
-
isozyme 1, 50% inhibition at 0.0007 mM, isozyme 2, 50% inhibition at 0.009 mM
DCM-extract of Angelicae dahuricae radix
0.1% inhibition of PGHS-1; 38.8% inhibition of PGHS-2
-
DCM-extract of Angelicae sinsesis radix
55.8% inhibition of PGHS-2; 75.0% inhibition of PGHS-1
-
DCM-extract of Atractylodis lanceae rhizoma
46.9% inhibition of PGHS-1; 50.3% inhibition of PGHS-2
-
DCM-extract of Atractylodis macrocephalae rhizoma
47.0% inhibition of PGHS-2; 58.6% inhibition of PGHS-1
-
DCM-extract of Cinnamomi ramulus
48.4% inhibition of PGHS-2; 73.5% inhibition of PGHS-1
-
DCM-extract of Houttuyniae herba
40.9% inhibition of PGHS-2; 46.8% inhibition of PGHS-1
-
DCM-extract of Notopterygii rhizoma seu radix
-2.1% inhibition of PGHS-2; 42.6% inhibition of PGHS-1
-
DCM-extract of Piperis sarmentosi herba
10.1% inhibition of PGHS-2; 47.2% inhibition of PGHS-1
-
DCM-extract of Platycodi radix
70.1% inhibition of PGHS-2; 77.8% inhibition of PGHS-1
-
DCM-extract of Zanthoxyli pericarpium
18.3% inhibition of PGHS-1; 31.3% inhibition of PGHS-2
-
DCM-extract of Zingiberis rhizoma
41.3% inhibition of PGHS-2; 52.9% inhibition of PGHS-1
-
docosahexaenoic acid
-
isozyme 1, 50% inhibition at 0.011 mM, isozyme 2, 50% inhibition at 0.015 mM
ellagic acid
-
at high concentration and in presence of cofactors inhibition, at low concentrations stimulation
fenclofenac
-
isozyme 1, 50% inhibition at 0.007 mM, isozyme 2, 50% inhibition at 0.004 mM
L-745
-
isozyme 1, 50% inhibition at 0.369 mM, isozyme 2, 50% inhibition at 0.002 mM
Mefenamic acid
-
isozyme 1, 50% inhibition at 0.01 mM, isozyme 2, 50% inhibition at 0.0003 mM
meloxicam
-
isozyme 1, 50% inhibition at 0.005 mM, isozyme 2, 50% inhibition at 0.0004 mM
n-hexane extract of Angelicae dahuricae radix
42.4% inhibition of PGHS-2; 52.5% inhibition of PGHS-1
-
n-hexane extract of Angelicae sinsesis radix
61.5% inhibition of PGHS-2; 73.0% inhibition of PGHS-1
-
n-hexane extract of Atractylodis lanceae rhizoma
67.4% inhibition of PGHS-1; 68.3% inhibition of PGHS-2
-
n-hexane extract of Atractylodis macrocephalae rhizoma
46.1% inhibition of PGHS-1; 48.9% inhibition of PGHS-2
-
n-hexane extract of Cinnamomi ramulus
23.6% inhibition of PGHS-2; 46.6% inhibition of PGHS-1
-
n-hexane extract of Houttuyniae herba
43.4% inhibition of PGHS-2; 50.3% inhibition of PGHS-1
-
n-hexane extract of Notopterygii rhizoma seu radix
64.9% inhibition of PGHS-2; 69.6% inhibition of PGHS-1
-
n-hexane extract of Piperis sarmentosi herba
52.4% inhibition of PGHS-1; 65.0% inhibition of PGHS-2
-
n-hexane extract of Platycodi radix
48.7% inhibition of PGHS-1; 55.1% inhibition of PGHS-2
-
n-hexane extract of Zanthoxyli pericarpium
24.9% inhibition of PGHS-2; 48.5% inhibition of PGHS-1
-
n-hexane extract of Zingiberis rhizoma
77.5% inhibition of PGHS-2; 83.4% inhibition of PGHS-1
-
niflumic acid
-
isozyme 1, 50% inhibition at 0.016 mM, isozyme 2, 50% inhibition at 0.0001 mM
O2
-
the cyclooxygenase reaction is inhibited by an excess of dissolved oxygen, 0.5 mM O2 causes twofold decrease in the initial rate and maximal yield
PD-98059
MEK inhibitor, blocks specifically the activation of ERK1/2 and the PGHS-2 mRNA response to oxygen and glucose depivation, hence ERK is a mediator of PGHS-2 gene expression
SB203580
inhibitor of p38, reduces the PGHS-2 response to oxygen and glucose depivation by approximately 50%
SC58125
-
isozyme 1, 50% inhibition at 0.039 mM, isozyme 2, 50% inhibition at 0.0003 mM
sulindac sulfide
-
isozyme 1, 50% inhibition at 0.0004 mM, isozyme 2, 50% inhibition at 0.012 mM
suprofen
-
isozyme 1, 50% inhibition at 0.0005 mM, isozyme 2, 50% inhibition at 0.002mM
Tannic acid
-
at high concentration and in presence of cofactors inhibition, at low concentrations stimulation
U0126
MEK inhibitor, blocks specifically the activation of ERK1/2 and the PGHS-2 mRNA response to oxygen and glucose depivation, hence ERK is a mediator of PGHS-2 gene expression
5-bromo-2-[4-fluorophenyl]-3-[4-methylsulfonylphenyl]-thiophene
-
DuP-697, selective for isozyme 2
5-bromo-2-[4-fluorophenyl]-3-[4-methylsulfonylphenyl]-thiophene
-
50% inhibition at 8.7 nM
Acetylsalicylic acid
-
isozyme 1, complete inhibition, isozyme 2, change in reaction, main product from arachidonate is 15-hydroxyeicosatetraenoic acid
Acetylsalicylic acid
-
inhibition of oxygenase activity by acetylating a serine residue of the enzyme
albumin
-
bovine serum albumin inhibits by binding of arachidonic acid
-
diclofenac
-
isozyme 1, 50% inhibition at 0.0009 mM, isozyme 2, 50% inhibition at 0.0015 mM
diclofenac
-
isozyme 1, 50% inhibition at 0.0003 mM, isozyme 2, 50% inhibition at 18 nM
flurbiprofen
-
isozyme 1, 50% inhibition at 40 nM, isozyme 2, 50% inhibition at 500 nM
flurbiprofen
-
isozyme 1, 50% inhibition at 0.0009 mM, isozyme 2, 50% inhibition at 0.0009 mM
flurbiprofen
-
isozyme 1, 50% inhibition at 0.0005 mM, isozyme 2, 50% inhibition at 0.003 mM
Ibuprofen
-
isozyme 1, 50% inhibition at 0.0026 mM, isozyme 2, 50% inhibition at 0.0015 mM
Ibuprofen
-
isozyme 1, 50% inhibition at 0.009 mM, isozyme 2, 50% inhibition at 0.018 mM
Ibuprofen
-
isozyme 1, 50% inhibition at 0.09 mM, isozyme 2, 50% inhibition at 0.008 mM
indomethacin
-
isozyme 1, 50% inhibition at 0.0017 mM, isozyme 2, 50% inhibition at 0.025 mM
indomethacin
-
isozyme 1 50% inhibition at 0.0005 mM, isozyme 2, 50% inhibition at 0.0003 mM
indomethacin
-
isozyme 1, 50% inhibition at 0.005 mM, isozyme 2, 50% inhibition at 0.130-0.160 mM
Ketoprofen
-
isozyme 1, 50% inhibition at 0.0005 mM, isozyme 2, 50% inhibition at 0.0025 mM
Ketoprofen
-
isozyme 1, 50% inhibition at 0.011 mM, isozyme 2, 50% inhibition at 0.018 mM
Meclofenamic acid
-
isozyme 1, 50% inhibition at 0.002 mM, isozyme 2, 50% inhibition at 0.015 mM
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
little inhibition in gastrointestinal tissues
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
NS-398, selective for isozyme 2
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
isozyme 1, 50% inhibition at 0.075 mM, isozyme 2, 50% inhibition at 0.002 mM
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
little inhibition in gastrointestinal tissues
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
isozyme 1, 50% inhibition at 0.017 mM, isozyme 2, 50% inhibition at 0.0001 mM
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
little inhibition in gastrointestinal tissues
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
little inhibition in gastrointestinal tissues
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
-
little inhibition in gastrointestinal tissues
naproxen
-
isozyme 1, 50% inhibition at 0.0006 mM, isozyme 2, 50% inhibition at 0.002 mM
naproxen
inhibitor of cyclooxigenase reaction; inhibitor of cyclooxigenase reaction
nimesulide
-
isozyme 1, 50% inhibition at 0.07 mM, isozyme 2, 50% inhibition at 0.0013 mM
nimesulide
-
isozyme 1, 50% inhibition at 0.009 mM, isozyme 2, 50% inhibition at 0.0005 mM
piroxicam
-
isozyme 1, 50% inhibition at 0.009-0.024 mM, isozyme 2, 50% inhibition at 0.070-0.240 mM
piroxicam
-
isozyme 1, 50% inhibition at 0.075 mM, isozyme 2, 50% inhibition at 0.002 mM
additional information
algal PGHS is not inhibited by non-steroidal anti-inflammatory drugs that inhibit the mammalian enzymes
-
additional information
-
algal PGHS is not inhibited by non-steroidal anti-inflammatory drugs that inhibit the mammalian enzymes
-
additional information
-
effect of cofactor, enzyme and substrate concentration on inhibition by human serum, haptoglobin and albumin
-
additional information
guava leaf extract inhibits the catalytic activity of the PGHS-1 isoform using linoleic acid as substrate (IC50 value of 0.055 mg of dry leaf extract); guava leaf extract inhibits the catalytic activity of the PGHS-2 isoform using linoleic acid as substrate (IC50 value of 0.56 mg of dry leaf extract); isozyme PGHS-1 is hardly inhibited by ellagic acid; isozyme PGHS-2 is hardly inhibited by ellagic acid
-
additional information
guava leaf extract inhibits the catalytic activity of the PGHS-1 isoform using linoleic acid as substrate (IC50 value of 0.055 mg of dry leaf extract); guava leaf extract inhibits the catalytic activity of the PGHS-2 isoform using linoleic acid as substrate (IC50 value of 0.56 mg of dry leaf extract); isozyme PGHS-1 is hardly inhibited by ellagic acid; isozyme PGHS-2 is hardly inhibited by ellagic acid
-
additional information
-
guava leaf extract inhibits the catalytic activity of the PGHS-1 isoform using linoleic acid as substrate (IC50 value of 0.055 mg of dry leaf extract); guava leaf extract inhibits the catalytic activity of the PGHS-2 isoform using linoleic acid as substrate (IC50 value of 0.56 mg of dry leaf extract); isozyme PGHS-1 is hardly inhibited by ellagic acid; isozyme PGHS-2 is hardly inhibited by ellagic acid
-
additional information
no inhibition of PGHS-2 oxygenase activity by 9-nitro-, 12-nitro-, 14-nitro, and 15-nitroarachidonic acid and by nitrooleic acid and nitrolinoleic acid; other nitro fatty acids tested, such as nitrooleic acid and nitrolinoleic acid, are unable to inhibit the enzyme activity
-
additional information
no inhibition of PGHS-2 oxygenase activity by 9-nitro-, 12-nitro-, 14-nitro, and 15-nitroarachidonic acid and by nitrooleic acid and nitrolinoleic acid; other nitro fatty acids tested, such as nitrooleic acid and nitrolinoleic acid, are unable to inhibit the enzyme activity
-
additional information
-
no inhibition of PGHS-2 oxygenase activity by 9-nitro-, 12-nitro-, 14-nitro, and 15-nitroarachidonic acid and by nitrooleic acid and nitrolinoleic acid; other nitro fatty acids tested, such as nitrooleic acid and nitrolinoleic acid, are unable to inhibit the enzyme activity
-
additional information
nimesulide inhibits PGHS-2 turnover in most brain regions
-
additional information
nimesulide inhibits PGHS-2 turnover in most brain regions
-
additional information
-
nimesulide inhibits PGHS-2 turnover in most brain regions
-
additional information
guava leaf extract inhibits the catalytic activity of the PGHS-1 and PGHS-2 isoforms using linoleic acid as substrate; guava leaf extract inhibits the catalytic activity of the PGHS-1 and PGHS-2 isoforms using linoleic acid as substrate; isozyme PGHS-1 is hardly inhibited by ellagic acid; isozyme PGHS-2 is hardly inhibited by ellagic acid
-
additional information
guava leaf extract inhibits the catalytic activity of the PGHS-1 and PGHS-2 isoforms using linoleic acid as substrate; guava leaf extract inhibits the catalytic activity of the PGHS-1 and PGHS-2 isoforms using linoleic acid as substrate; isozyme PGHS-1 is hardly inhibited by ellagic acid; isozyme PGHS-2 is hardly inhibited by ellagic acid
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ellagic acid
-
at high concentration and in presence of cofactors inhibition, at low concentrations stimulation
glutathione
promotes prostaglandin H synthase-dependent formation of oxidative stress biomarkers malondialdehyde and 15(S)-8-iso-prostaglandin F2alpha
peroxynitrite
-
peroxidase activity, MS-analysis reveals that tyrosine 385 is a target for nitration by ONOO- only when heme is present
Tannic acid
-
at high concentration and in presence of cofactors inhibition, at low concentrations stimulation
additional information
-
USF proteins are involved in the trans-activation of the PGH-2 promoter in granulosa cells
-
additional information
the enzyme is induced by arachidonic acid up to 7.5-fold within 6 h, it is also induced by protein kinase C activators 4beta-PMA and PGF2alpha, all activation effects are blocked by PKC inhibitors, regulation, overview, protein kinase C induces PTGS2 independently of PPARs, i.e. peroxisome-proliferator-activated receptors
-
additional information
-
the enzyme is induced by arachidonic acid up to 7.5-fold within 6 h, it is also induced by protein kinase C activators 4beta-PMA and PGF2alpha, all activation effects are blocked by PKC inhibitors, regulation, overview, protein kinase C induces PTGS2 independently of PPARs, i.e. peroxisome-proliferator-activated receptors
-
additional information
-
cyclooxygenase catalysis by prostaglandin H synthase-1 and -2 requires activation of the normally latent enzyme by peroxide-dependent generation of a free radical at Tyr385 (PGHS-1 numbering) in the cyclooxygenase active site. The Tyr385 radical has also been linked to self-inactivation processes that impose an ultimate limit on cyclooxygenase catalysis
-
additional information
hypoxia and glucose-free medium treatment synergistically increase PGHS-2 mRNA approximately 8fold
-
additional information
oxygen and glucose depivation induce PGHS-2 gene expression synergistically in neurons
-
additional information
-
aqueous extracts of Chromoleana odorata, commonly used in traditional medicine as antiinflammatory drug against pains or as cataplasm to stop hemorrhage in Ivory Coast, the essential oil extracted from the fresh leaves activates the cyclooxygenase activity of the PGHS, overview
-
additional information
-
stimulation of enzyme in crude extract by some amines
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0368
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
0.00945
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
0.0009
arachidonate
purified isoform PGHS-2, method: coupled, homo-vanilic acid
0.0027
arachidonate
purified isoform PGHS-1, method: coupled, homo-vanilic acid
0.00514
arachidonate
pH 8.0, 25°C, COX-2 wild-type COX-2 and mutant N580A
0.01
arachidonate
purified isoform PGHS-2, method: direct, arachidonate
0.01
arachidonate
purified isoform PGHS-2, method: direct, trimethyl phosphine oxide
0.0102
arachidonate
purified isoform PGHS-1, method: direct, arachidonate
0.011
arachidonate
purified isoform PGHS-1, method: coupled, homo-vanilic acid
0.0055
linoleic acid
isozyme PGHS-1, in 100 mM Tris-HCl buffer (pH 7.4), at 24°C
0.0068
linoleic acid
isozyme PGHS-2, in 100 mM Tris-HCl buffer (pH 7.4), at 24°C
0.0083
N,N,N',N'-tetramethyl-p-phenylenediamine
-
pH 7.2, 30°C, mutant enzyme N383H
0.01
N,N,N',N'-tetramethyl-p-phenylenediamine
-
pH 7.2, 30°C, mutant enzyme N383D
0.0156
N,N,N',N'-tetramethyl-p-phenylenediamine
-
pH 7.2, 30°C, mutant enzyme N382D
0.0163
N,N,N',N'-tetramethyl-p-phenylenediamine
-
pH 7.2, 30°C, PGHS-2 wild-type enzyme
0.0854
N,N,N',N'-tetramethyl-p-phenylenediamine
-
pH 7.2, 30°C, mutant enzyme N382L
0.103
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y148F/Y348F/Y385F/Y404F/Y504F
0.37
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y148F/Y348F/Y404F/Y504F
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
-
Michaelis-Menten kinetics
-
additional information
additional information
Michaelis-Menten kinetics, overview
-
additional information
additional information
-
Michaelis-Menten kinetics, overview
-
additional information
additional information
-
the cyclooxygenase reaction shows Michaelis-Menten kinetics over a wide range of oxygen concentrations in the absence of electron donor. Kinetics analysis, overview
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3.45
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
8.7
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
9
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
920
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
inhibition kinetics of the isozymes' peroxidase activity, overview
-
additional information
additional information
inhibition kinetics of the isozymes' peroxidase activity, overview
-
additional information
additional information
-
inhibition kinetics of the isozymes' peroxidase activity, overview
-
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0186
peroxynitrite
Ovis aries
-
cyclooxygenase activity, peroxynitrite is incubated with the resting enzyme and 30 s later, activity and protein nitration is analyzed
0.0222
peroxynitrite
Ovis aries
-
peroxidase activity, peroxynitrite is incubated with the resting enzyme and 30 s later, activity and protein nitration is analyzed
0.03
peroxynitrite
Ovis aries
-
cyclooxygenase activity, enzyme is incubated with peroxynitrite in the presence of peroxides and arachidonic acid
0.0388
peroxynitrite
Ovis aries
-
peroxidase activity, enzyme is incubated with peroxynitrite in the presence of peroxides and arachidonic acid
0.018
quercetin
Homo sapiens
isozyme PGHS-1, in 100 mM Tris-HCl buffer (pH 7.4), at 24°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
15000
cyclooxygenase activity for partially purified prostaglandin H synthase 2 of Salvelinus fontinalis, tPGHS-2
2300
cyclooxygenase activity for partially purified prostaglandin H synthase 1 of Salvelinus fontinalis, tPGHS-1
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2
7.4
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 9
-
about 70% of maximum activity at pH 6.0 and 9.0 of prostaglandin E2 formation, about 50% of maximum activity at pH 6.0 and 9.0 of prostaglandin F2alpha formation
7.2 - 9
-
about 60% of maximum activity at pH 7.2 and 9.0 of prostaglandin D2 formation
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
22
23
25
30
37
23
room temperature, 22-23°C, lipoxygenase activity assay
25
cyclooxygenase activity assay using a standard electrode
30
cyclooxygenase activity assay using a high sensitivity electrode
30
cyclooxygenase activity assay using a high sensitivity electrode
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 30
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
collected from the coast of Kanagawa Prefecture in Tokyo Bay
UniProt
brenda
collected on the coast of the Baltic Sea in Kassari Bay
UniProt
brenda
a homology modeling structure of human PGHS-1 is constructed using the Swiss-Model server and the ovine crystal structure 1Q4G as template
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
seminal plasma induces and potentiates the expression of PTGS2 in cervicovaginal cells and tissues
brenda
vaginal cell line, expression of prostaglandin-endoperoxide synthase 2, i.e. cyclooxygenase 2, in human vaginal cells in response to toll-like receptor ligands and other proinflammatory stimuli, such vaginal mucosal irritant nonoxynol-9, in a synergistic manner
brenda
additional information
PGHS-2 has lowest abundance in brain stem and pituitary gland
brenda
PGSHS-1 has lowest abundance in brain stem and pituitary gland
brenda
PGHS-2 has highest abundance in hippocampus and cerebral cortex
brenda
PGSHS-1 has highest abundance in hippocampus and cerebral cortex
brenda
PTGS1 enzyme activity is higher in late corpora lutea and lower in regressive ones
brenda
PTGS2 increases from early to late corpora lutea and lowers in regressive ones
brenda
-
significant increase in mRNA for PGHS-2 after treatment with prostaglandin F2alpha. PGHS-1 mRNA content remains unchanged
brenda
PGHS-2 has highest abundance in hippocampus and cerebral cortex
brenda
PGSHS-1 has highest abundance in hippocampus and cerebral cortex
brenda
PGHS-2 has lowest abundance in brain stem and pituitary gland
brenda
PGSHS-1 has lowest abundance in brain stem and pituitary gland
brenda
-
-
438369, 438371, 438374, 438379, 438381, 438383, 438384, 438385, 438387, 438388, 659705, 671047, 673508, 673809, 675273, 713706
brenda
additional information
-
enzyme can be associated with endoplasmic reticulum, nuclear envelope and plasma membrane even within the same cell
brenda
additional information
-
distribution of isozymes 1,2 in gastrointestinal tissues
brenda
additional information
-
enzyme can be associated with endoplasmic reticulum, nuclear envelope and plasma membrane even within the same cell
brenda
additional information
-
distribution of isozymes 1,2 in gastrointestinal tissues
brenda
additional information
quantitative real-time RT-PCR enzyme expression analysis, overview
brenda
additional information
quantitative RT-PCR enzyme expression and immunohistochemic analysis, overview
brenda
additional information
-
quantitative RT-PCR enzyme expression and immunohistochemic analysis, overview
brenda
additional information
-
distribution of isozymes 1,2 in gastrointestinal tissues
brenda
additional information
-
enzyme can be associated with endoplasmic reticulum, nuclear envelope and plasma membrane even within the same cell
brenda
additional information
relationship of PGHS-2 and PGHS-1 mRNA and activity in brain tissues, overview
brenda
additional information
relationship of PGHS-2 and PGHS-1 mRNA and activity in brain tissues, overview
brenda
additional information
-
relationship of PGHS-2 and PGHS-1 mRNA and activity in brain tissues, overview
brenda
additional information
-
distribution of isozymes 1,2 in gastrointestinal tissues
brenda
additional information
-
distribution of isozymes 1,2 in gastrointestinal tissues
brenda
additional information
-
enzyme can be associated with endoplasmic reticulum, nuclear envelope and plasma membrane even within the same cell
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
immunoreactive PGHS-2 is localized to the cytoplasm of amnion epithelial cells, amnion-chorion mesenchymal cells, and chorion trophoblast cells and in scattered stromal cells
brenda