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(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid + AH2 + O2
? + A + H2O
substrate binding structure and nonproductive conformation, overview
-
?
8,11,14-eicosatrienoic acid + O2
prostaglandin G1 + ?
8,11,14-eicosatrienoic acid + O2
prostaglandin H1 + ?
alpha-linolenic acid + reduced acceptor + O2
?
arachidonate + 2 O2
prostaglandin G2
-
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin G2 + A + H2O
arachidonate + AH2 + 2 O2
prostaglandin H2 + A + H2O
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
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(R)-hydroxy-eicosatetraenoic acid + A + H2O
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 + AH2 + 2 O2
prostaglandin E2 + A + H2O
-
-
-
?
arachidonic acid + AH2 + O2
prostaglandin E2 + A + H2O
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
cis-11,14-eicosadienoic acid + AH2 + O2
?
-
-
?
cis-11,14-eicosadienoic acid + reduced acceptor + O2
?
-
-
-
r
cis-4,7,10,13,16,19-docosahexaenoic acid + AH2 + O2
?
-
-
?
cis-5,8,11,14,17-eicosapentaenoic acid + AH2 + O2
?
-
-
?
cis-5,8,11,14,17-eicosapentaenoic acid + reduced acceptor + O2
?
cis-5,8,11,14-eicosatetraenoic acid + AH2 + O2
?
-
-
?
cis-7,10,13,16-docosatetraenoic acid + AH2 + O2
?
-
-
?
cis-7,10,13,16-docosatetraenoic acid + reduced acceptor + O2
?
cis-8,11,14-eicosatrienoic acid + AH2 + O2
?
-
-
?
cis-8,11,14-eicosatrienoic acid + reduced acceptor + O2
?
gamma-linolenic acid + AH2 + O2
?
-
-
?
gamma-linolenic acid + reduced acceptor + O2
?
guaiacol + trans-5-phenyl-4-pentenyl-1-hydroperoxide
?
-
-
-
?
H2O2 + guaiacol
?
-
peroxidase activity
-
?
H2O2 + N,N,N',N'-tetramethyl-p-phenylenediamine
?
-
peroxidase activity
-
?
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
linolenic acid + AH2 + O2
?
-
-
?
prostaglandin G2 + AH2
prostaglandin H2 + A + H2O
-
-
-
?
additional information
?
-
(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
-
-
-
?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
-
-
?
8,11,14-eicosatrienoic acid + O2

prostaglandin G1 + ?
-
-
-
?
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 + ?
-
-
-
?
8,11,14-eicosatrienoic acid + O2
prostaglandin H1 + ?
-
hydroperoxidase activity, presence of hematin and tryptophan
-
?
alpha-linolenic acid + reduced acceptor + O2

?
-
-
-
r
alpha-linolenic acid + reduced acceptor + O2
?
-
-
r
arachidonate + AH2 + 2 O2

prostaglandin G2 + A + H2O
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin G2 + A + H2O
-
-
?
arachidonate + AH2 + 2 O2

prostaglandin H2 + A + H2O
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin H2 + A + H2O
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin H2 + 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 + 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 + AH2 + O2
prostaglandin H2 + A + H2O
-
-
?
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
-
-
?
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 + AH2 + O2
prostaglandin H2 + A + H2O
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
?
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
?
arachidonic acid + AH2 + O2

prostaglandin E2 + A + H2O
-
-
?
arachidonic acid + AH2 + O2
prostaglandin E2 + A + H2O
-
-
?
cis-5,8,11,14,17-eicosapentaenoic acid + reduced acceptor + O2

?
-
-
-
r
cis-5,8,11,14,17-eicosapentaenoic acid + reduced acceptor + O2
?
-
-
r
cis-7,10,13,16-docosatetraenoic 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
cis-8,11,14-eicosatrienoic acid + reduced acceptor + O2
?
-
-
r
gamma-linolenic acid + reduced acceptor + O2

?
-
-
-
r
gamma-linolenic 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
?
-
-
PGHS-2 also shows cyclooxygenase activity
-
?
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-1 also exhibits peroxidase activity
-
?
additional information
?
-
PGHS-2 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
?
-
-
-
-
?
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
?
-
-
first step in prostaglandin synthesis
-
?
additional information
?
-
-
first step in prostaglandin synthesis
-
?
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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1,10-phenanthroline
-
weak
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
2,3-Dimercaptopropanol
-
inhibition of prostaglandin G1 synthesis
2-hydroxybutyric acid
-
weak
3,6-bis(3-[[(furan-2-yl)methyl]amino]propyl)-9H-xanthen-9-one
-
3,6-bis(5-[[(furan-2-yl)methyl]amino]pentyl)-9H-xanthen-9-one
-
3,6-bis[3-(2-methyl-1H-indol-1-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(4-methylpiperazin-1-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(4-nitroanilino)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(cyclohexylamino)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(morpholin-4-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(piperidin-1-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(1H-pyrazol-3-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(2-chloropyridin-3-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(4H-1,2,4-triazol-4-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(pyrazin-2-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(pyridin-2-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[4-(1H-imidazol-2-yl)butyl]-9H-xanthen-9-one
-
3,6-bis[5-(2-methyl-1H-indol-1-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(4-methylpiperazin-1-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(4-nitroanilino)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(cyclohexylamino)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(morpholin-4-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(piperidin-1-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(1H-pyrazol-3-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(2-chloropyridin-3-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(4H-1,2,4-triazol-4-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(piperidin-1-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(pyrazin-2-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(pyridin-2-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[6-(1H-imidazol-2-yl)hexyl]-9H-xanthen-9-one
-
5,8,11,14-Eicosatetraynoic acid
5-bromo-2-[4-fluorophenyl]-3-[4-methylsulfonylphenyl]-thiophene
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
bicarbonate
-
bicarbonate enhances peroxynitrite-mediated peroxidase inactivation
BW 755C
-
recombinant protein, 50% inhibition at 0.01-0.02 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
-
diethyldithiocarbamate
-
-
dihydrolipoic acid
-
inhibition of prostaglandin G1 synthesis
dithiothreitol
-
inhibition of prostaglandin G1 synthesis
docosahexaenoic acid
-
isozyme 1, 50% inhibition at 0.011 mM, isozyme 2, 50% inhibition at 0.015 mM
Eicosa-5,8,11,14-tetraynoic acid
-
-
ellagic acid
-
at high concentration and in presence of cofactors inhibition, at low concentrations stimulation
etodalac
-
recombinant protein, 50% inhibition at 0.06-0.07 mM
ETYA
-
recombinant protein, 50% inhibition at 0.015-0.025 mM
fatty acid
-
of low molecular mass
fenclofenac
-
isozyme 1, 50% inhibition at 0.007 mM, isozyme 2, 50% inhibition at 0.004 mM
flosulide
-
selective for isozyme 2, 50% inhibition at 130 nM
Flufenamic acid
-
50% inhibition at 0.02 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
-
N-[2-cyclohexyloxy-4-nitrophenyl]methanesulfonamide
niflumic acid
-
isozyme 1, 50% inhibition at 0.016 mM, isozyme 2, 50% inhibition at 0.0001 mM
Non-steroidal anti-inflammatory agents
-
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
5,8,11,14-Eicosatetraynoic acid

-
-
5,8,11,14-Eicosatetraynoic acid
complete inhibition at 0.04 mM
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

-
inhibition of prostaglandin G1 synthesis
Acetylsalicylic acid
-
an irreversible inhibitor of both hPHS-1 and hPHS-2
Acetylsalicylic acid
-
isozyme 1, complete inhibition, isozyme 2, change in reaction, main product from arachidonate is 15-hydroxyeicosatetraenoic acid
Acetylsalicylic acid
-
irreversible inhibitor
Acetylsalicylic acid
-
inhibition of oxygenase activity by acetylating a serine residue of the enzyme
albumin

-
-
-
albumin
-
bovine serum albumin inhibits by binding of arachidonic acid
-
aspirin

-
-
aspirin
-
cyclooxygenase activity
diclofenac

-
recombinant protein, 50% inhibition at 0.04 mM
diclofenac
-
50% inhibition at 9.4 nM
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
DUP-697

-
a standard PHS-2 inhibitor
DUP-697
-
a PHS-2-specific inhibitor
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
flurbiprofen
-
cyclooxygenase inhibitor
Ibuprofen

-
recombinant protein, 50% inhibition at 0.04 mM
Ibuprofen
-
50% inhibition at 0.253 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

-
inhibition of prostaglandin G1 synthesis
indomethacin
-
acts on isozyme 1 and 2, 85% inhibition at 100 nM
indomethacin
-
inhibition in gastrointestinal tissues
indomethacin
-
reversible and time-dependent inhibition
indomethacin
-
50% inhibition at 100 nM
indomethacin
-
isozyme 1, 50% inhibition at 0.0017 mM, isozyme 2, 50% inhibition at 0.025 mM
indomethacin
-
inhibition in gastrointestinal tissues
indomethacin
-
isozyme 1 50% inhibition at 0.0005 mM, isozyme 2, 50% inhibition at 0.0003 mM
indomethacin
-
inhibition in gastrointestinal tissues
indomethacin
-
isozyme 1, 50% inhibition at 0.005 mM, isozyme 2, 50% inhibition at 0.130-0.160 mM
indomethacin
-
inhibition in gastrointestinal tissues
indomethacin
-
inhibition in gastrointestinal tissues
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
-
50% inhibition at 81 nM
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

-
recombinant protein, 50% inhibition at 0.05-0.06 mM
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
nimesulide
-
inhibits the cyclooxygenase activity, a COX-2-specific inhibitor
Non-steroidal anti-inflammatory agents

-
inhibition of cyclooxygenase activity
-
Non-steroidal anti-inflammatory agents
-
inhibition of cyclooxygenase activity
-
NS-398

inhibits PTGS2
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
quercetin

-
quercetin 3-O-glucoside

-
quercetin 3-O-glucoside
-
SC-560

-
a standard PHS-1 inhibitor
SC-560
-
a PHS-1-specific inhibitor
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
-
mechanism of selective inhibition
-
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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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
0.0031 - 0.082
alpha-linolenic acid
0.0009 - 0.015
arachidonate
0.001 - 0.16
arachidonic acid
0.0052 - 0.0091
cis-11,14-eicosadienoic acid
0.0011 - 0.07
cis-4,7,10,13,16,19-docosahexaenoic acid
0.0012 - 0.039
cis-5,8,11,14,17-eicosapentaenoic acid
0.0017 - 0.013
cis-5,8,11,14-eicosatetraenoic acid
0.0027 - 0.061
cis-7,10,13,16-docosatetraenoic acid
0.002 - 0.036
cis-8,11,14-eicosatrienoic acid
0.0048 - 0.162
gamma-linolenic acid
0.0055 - 0.0068
linoleic acid
0.0083 - 0.0854
N,N,N',N'-tetramethyl-p-phenylenediamine
0.02 - 0.437
trans-5-phenyl-4-pentenyl-1-hydroperoxide
additional information
additional information
-
0.0031
alpha-linolenic acid

-
0.0048
alpha-linolenic acid
-
-
0.0101
alpha-linolenic acid
-
0.082
alpha-linolenic acid
-
0.0009
arachidonate

purified isoform PGHS-2, method: coupled, homo-vanilic acid
0.0011
arachidonate
purified isoform PGHS-2, method: direct, O2
0.0017
arachidonate
purified isoform PGHS-2, method: direct, O2
0.0019
arachidonate
purified isoform PGHS-1, method: direct, O2
0.002
arachidonate
purified isoform PGHS-2, method: direct, O2
0.0021
arachidonate
-
native enzyme
0.0021
arachidonate
-
pH 7.2, 30°C, mutant enzyme N382L
0.0021
arachidonate
-
pH 7.2, 30°C, PGHS-2 wild-type enzyme
0.0022
arachidonate
-
pH 7.2, 30°C, mutant enzyme N383D
0.0027
arachidonate
purified isoform PGHS-1, method: coupled, homo-vanilic acid
0.0029
arachidonate
-
pH 7.2, 30°C, mutant enzyme N382D
0.00295
arachidonate
pH 8.0, 25°C, COX-2 mutant L531P
0.003
arachidonate
purified isoform PGHS-1, method: direct, O2
0.0032
arachidonate
-
mutant enzyme Y148F
0.0036
arachidonate
-
mutant enzyme Y404F
0.00365
arachidonate
pH 8.0, 25°C, COX-2 mutant L531A
0.0037
arachidonate
-
pH 7.2, 30°C, mutant enzyme N383H
0.0037
arachidonate
purified isoform PGHS-1, method: direct, O2
0.0038
arachidonate
-
mutant enzyme Y348F
0.0041
arachidonate
-
pH 7.2, 30°C, mutant enzyme N382A
0.0042
arachidonate
-
mutant enzyme Y504F
0.0043
arachidonate
-
mutant enzyme Y148F/Y348F/Y404F/Y504F
0.0045
arachidonate
purified isoform PGHS-1, method: direct, O2
0.005
arachidonate
purified isoform PGHS-2, method: direct, O2
0.0051
arachidonate
purified isoform PGHS-2, method: direct, O2
0.00514
arachidonate
pH 8.0, 25°C, COX-2 wild-type COX-2 and mutant N580A
0.009
arachidonate
purified isoform PGHS-2, method: direct, O2
0.0092
arachidonate
purified isoform PGHS-2, method: direct, O2
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
0.015
arachidonate
purified isoform PGHS-1, method: direct, O2
0.001
arachidonic acid

-
isozyme 1 and 2
0.0021
arachidonic acid
-
wild-type, cyclooxygenase activity
0.0034
arachidonic acid
-
mutant Y348F/Y504F, cyclooxygenase activity
0.0038
arachidonic acid
-
mutant Y348F, cyclooxygenase activity
0.0042
arachidonic acid
-
mutant Y504F, cyclooxygenase activity
0.0045
arachidonic acid
-
isozyme 1
0.005
arachidonic acid
-
isozyme 2
0.006
arachidonic acid
-
-
0.0083
arachidonic acid
-
-
0.015
arachidonic acid
-
-
0.16
arachidonic acid
-
-
0.0052
cis-11,14-eicosadienoic acid

-
0.0091
cis-11,14-eicosadienoic acid
-
-
0.0011
cis-4,7,10,13,16,19-docosahexaenoic acid

-
0.0033
cis-4,7,10,13,16,19-docosahexaenoic acid
-
-
0.0318
cis-4,7,10,13,16,19-docosahexaenoic acid
-
0.07
cis-4,7,10,13,16,19-docosahexaenoic acid
-
0.0012
cis-5,8,11,14,17-eicosapentaenoic acid

-
0.0031
cis-5,8,11,14,17-eicosapentaenoic acid
-
-
0.0153
cis-5,8,11,14,17-eicosapentaenoic acid
-
0.039
cis-5,8,11,14,17-eicosapentaenoic acid
-
0.0017
cis-5,8,11,14-eicosatetraenoic acid

-
0.0024
cis-5,8,11,14-eicosatetraenoic acid
-
0.003
cis-5,8,11,14-eicosatetraenoic acid
-
-
0.013
cis-5,8,11,14-eicosatetraenoic acid
-
0.0027
cis-7,10,13,16-docosatetraenoic acid

-
0.007
cis-7,10,13,16-docosatetraenoic acid
-
-
0.0357
cis-7,10,13,16-docosatetraenoic acid
-
0.061
cis-7,10,13,16-docosatetraenoic acid
-
0.002
cis-8,11,14-eicosatrienoic acid

-
0.0055
cis-8,11,14-eicosatrienoic acid
-
-
0.0059
cis-8,11,14-eicosatrienoic acid
-
0.036
cis-8,11,14-eicosatrienoic acid
-
0.0048
gamma-linolenic acid

-
0.0071
gamma-linolenic acid
-
-
0.162
gamma-linolenic acid
-
0.08
guaiacol

-
pH 8.0, 23°C, wild-type enzyme
0.29
guaiacol
-
pH 8.0, 23°C, mutant enzyme N382L
1.3
H2O2

-
pH 8.0, 23°C, wild-type enzyme
5.5
H2O2
-
pH 8.0, 23°C, mutant enzyme N382L
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
0.005
O2

purified isoform PGHS-1, method: direct, O2
0.0055
O2
purified isoform PGHS-1, method: direct, O2
0.01
O2
purified isoform PGHS-1, method: direct, arachidonate
0.011
O2
purified isoform PGHS-1, method: direct, O2
0.02
trans-5-phenyl-4-pentenyl-1-hydroperoxide

-
mutant enzyme Y148F
0.061
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y404F
0.072
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y348F
0.103
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y148F/Y348F/Y385F/Y404F/Y504F
0.138
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
native enzyme
0.339
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y385F
0.37
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme Y148F/Y348F/Y404F/Y504F
0.437
trans-5-phenyl-4-pentenyl-1-hydroperoxide
-
mutant enzyme 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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