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(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
4-nitroacetophenone + NADPH
?
-
high activity
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzalcohol + NADP+
-
high activity
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
4-nitrobenzaldehyde + NADPH + H+
(4-nitrophenyl)methanol + NADP+
5beta-androstane-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
-
-
-
-
r
5beta-dihydrotestosterone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
9,10-phenanthrenequinone + NADPH
? + NADP+
-
-
-
?
9,10-phenanthrenequinone + NADPH + H+
?
-
-
-
?
9alpha,11beta-prostaglandin F2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
r
androst-4-ene-3,17-dione + NADPH
? + NADP+
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
D-xylose + NADPH
?
-
-
-
-
?
daunorubicin + NADPH
?
-
high activity
-
-
?
DL-glyceraldehyde + NADPH
DL-glycerol + NADP+
-
-
-
-
?
duroquinone + NADPH
?
-
-
-
-
?
n-butyraldehyde + NADPH
n-butanol + NADP+
-
-
-
-
?
p-nitroacetophenone + NADPH
?
-
-
-
-
?
prostaglandin A2 + NADPH
?
-
-
-
-
?
prostaglandin D1 + NADPH
?
-
-
-
-
?
prostaglandin D2 + NADP+
9alpha,11beta-prostaglandin F2 + NADPH
-
-
-
?
prostaglandin D2 + NADP+
9alpha,11beta-prostaglandin F2 + NADPH + H+
-
-
-
r
prostaglandin D2 + NADPH + H+
9-alpha,11-beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2alpha + NADP+
-
-
-
r
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2alphabeta + NADP+
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
prostaglandin D2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin D2 ethanolamide + NADPH
prostaglandin 9alpha,11beta-F2 ethanolamide + NADP+
i.e. prostamide D2
i.e. 91lpha,11beta-prostamide F2
-
?
prostaglandin D3 + NADPH
?
-
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
prostaglandin H2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
prostaglandin H2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
prostaglandin I2 + NADPH
?
-
-
-
-
?
prostamide D2 + NADPH + H+
9alpha,11beta-prostamide F2 + NADP+
-
-
-
?
prostamide H2 + NADPH + H+
prostamide F2alpha + NADP+
-
about 70% of prostamide H2 is converted to prostamide F2alpha after 2 min at 37°C
-
-
?
retinal + NADPH
retinol + NADP+
-
-
-
-
?
testosterone + NADPH + H+
?
-
-
-
-
?
ubiquinone-10 + NADPH
?
-
-
-
-
?
additional information
?
-
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
ir
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
transformation of endogenous prostaglandin D2 to prostaglandin F2alpha
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
prostaglandin F2alpha exhibits contraction of smooth muscles in the uterus, brochus trachea, luteolysis, the initiation of partutition and pain transmission
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
(4-nitrophenyl)methanol + NADP+
-
-
-
?
4-nitrobenzaldehyde + NADPH + H+
(4-nitrophenyl)methanol + NADP+
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
best substrate
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
i.e. PQ
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
i.e. PQ
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
i.e. PQ
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
i.e. PQ
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
-
high activity
-
-
?
hydrindantin + NADPH
?
-
-
-
-
?
hydrindantin + NADPH
?
-
high activity
-
-
?
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
?
-
high activity
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
phenylglyoxal + NADPH
?
-
high activity
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
-
reaction via formation of the endoperoxide ethanolamide intermediate prostaglandin H2
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion, i.e. 11-epi PGF2alpha
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
amino acid residues Arg27, Arg91, His170, Arg223, and Asn306 are involved in substrate binding
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion, i.e. 11-epi PGF2alpha
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion, i.e. 11-epi PGF2alpha
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion, i.e. 11-epi PGF2alpha
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
aldo-keto reductase has prostaglandin F2alpha synthase activity. AKR1B1 is a more efficient prostaglandin F2alpha synthase than AKR1C3
-
-
?
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
aldo-keto reductases AKR1B3 and AKR1B7 have prostaglandin F2alpha synthase activity
-
-
?
prostaglandin H2 + NADPH + H+
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
His170 is involved in binding, and Asn306 is critical for catalytic activity
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
r
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
no stereochemic determination/identification of the product
-
?
additional information
?
-
-
two different active sites, one for the endoperoxide group of prostaglandin H2 and the other one for the keto group of prostaglandin D2 and other carbonyl compounds
-
-
?
additional information
?
-
-
two different active sites, one for the endoperoxide group of prostaglandin H2 and the other one for the keto group of prostaglandin D2 and other carbonyl compounds
-
-
?
additional information
?
-
-
two different active sites, one for the endoperoxide group of prostaglandin H2 and the other one for the keto group of prostaglandin D2 and other carbonyl compounds
-
-
?
additional information
?
-
-
two different active sites, one for the endoperoxide group of prostaglandin H2 and the other one for the keto group of prostaglandin D2 and other carbonyl compounds
-
-
?
additional information
?
-
-
the enzyme is important for the production of lyteolytic prostaglandin F2alpha in the endometrium of cows, regulatory mechanisms, overview
-
-
?
additional information
?
-
-
the liver-type isozyme possesses two catalytic centres and a broad substrate specificity, D-xylose is a poor substrate, no activity with prostaglandin A1, prostaglandin B2, prostaglandin E2, 4-carboxybenzaldehyde, testosterone, 2,6-dichloroindophenol, D-glucose, D-glucuronic acid, and potassium ferricyanide, overview, the enzyme also exhibits aldose reductase, EC 1.1.1.21, and alcohol dehydrogenase, EC 1.1.1.1, activities, respectively
-
-
?
additional information
?
-
PGFS activity of the recombinant proteins is evaluated using an assay based on in situ generation of the precursor of prostaglandin PGH2 biosynthesis. PGF2alpha is measured by ELISA. Comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
-
-
?
additional information
?
-
-
PGFS activity of the recombinant proteins is evaluated using an assay based on in situ generation of the precursor of prostaglandin PGH2 biosynthesis. PGF2alpha is measured by ELISA. Comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
-
-
?
additional information
?
-
-
no activity with prostaglandin E2
-
-
?
additional information
?
-
no activity towards prostaglandin E2 synthesis
-
-
?
additional information
?
-
-
no activity towards prostaglandin E2 synthesis
-
-
?
additional information
?
-
-
the cytosolic enzyme synergistically interacts with cyclooxygenase 1 and 2, coupling, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
?
additional information
?
-
acive site structure, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity
-
-
?
additional information
?
-
-
substrate and product detection by liquid chromatographic-electrospray ionization-mass spectrometry
-
-
?
additional information
?
-
substrate and product detection by liquid chromatographic-electrospray ionization-mass spectrometry
-
-
?
additional information
?
-
Y55 and H117 are involved in catalysis, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity
-
-
?
additional information
?
-
-
Y55 and H117 are involved in catalysis, enzyme also shows 3alpha-hydroxysteroid dehydrogenase type II activity
-
-
?
additional information
?
-
-
the enzyme has dual activity as PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase
-
-
?
additional information
?
-
the enzyme has dual activity as PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase
-
-
?
additional information
?
-
-
PGFS does not catalyze the reduction of prostaglandin E2
-
-
?
additional information
?
-
PGFS does not catalyze the reduction of prostaglandin E2
-
-
?
additional information
?
-
in the absence of NADPH or NADP+, enzyme catalyzes the isomerization of prostaglandin H2 to prostaglandin D2 with a Km value of 0.023 mM. This activity of AKR1B1 increases with increasing pH, with an optimum of pH 8.5. Residue His110 acts as a base in concert with Asp43 and Lys77 and as an acid to generate PGD2 and PGF2a in the absence of NADPH or NADP+ and in the presence of NADPH, respectively
-
-
?
additional information
?
-
-
in the absence of NADPH or NADP+, enzyme catalyzes the isomerization of prostaglandin H2 to prostaglandin D2 with a Km value of 0.023 mM. This activity of AKR1B1 increases with increasing pH, with an optimum of pH 8.5. Residue His110 acts as a base in concert with Asp43 and Lys77 and as an acid to generate PGD2 and PGF2a in the absence of NADPH or NADP+ and in the presence of NADPH, respectively
-
-
?
additional information
?
-
AKR1C3 is overexpressed in keloids and mediates the conversion of PGD2 to 9alpha,11beta-PGF2 in keloid and normal fibroblasts
-
-
?
additional information
?
-
PGFS activity of the recombinant proteins is evaluated using an assay based on in situ generation of the precursor of prostaglandin PGH2 biosynthesis. PGF2alpha is measured by ELISA. Comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
-
-
?
additional information
?
-
-
PGFS activity of the recombinant proteins is evaluated using an assay based on in situ generation of the precursor of prostaglandin PGH2 biosynthesis. PGF2alpha is measured by ELISA. Comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
-
-
?
additional information
?
-
-
coupling ability between cyclooxygenase COX-2 and the prostanoid synthases performing the last stepes in the biosynthesis of prostaglandins PGE2, PGD2, PGF2alpha, and PGI2, regulation, overview, the 20alpha-hydroxysteroid dehydrogenase also shows prostaglandin F synthase activity in the endometrium during luteolysis
-
-
?
additional information
?
-
-
prostaglandin F synthase and prostaglandin F receptor are involved in the control of testosterone release from Leydig cells and in spermatogenesis via the local pathway and the hypothalamo-hypophysial-testis-pathway
-
-
?
additional information
?
-
-
no activity with prostaglandin D2 and prostaglandin E2
-
-
?
additional information
?
-
-
in the absence of NADPH or NADP+, enzyme catalyzes the isomerization of prostaglandin H2 to prostaglandin D2 with a Km value of 0.018 mM. This activity activity of AKR1B1 increases with increasing pH, with an optimum of pH 8.5. Residue His110 acts as a base in concert with Asp43 and Lys77 and as an acid to generate PGD2 and PGF2a in the absence of NADPH or NADP+ and in the presence of NADPH, respectively
-
-
?
additional information
?
-
-
enzyme shows no prostaglandin D2 11-ketoreductase activity, and no glutathione S-transferase activity, although it is similar to the glutathione S-transferase
-
-
?
additional information
?
-
-
enzyme interacts with cyclooxygenase 1 and 2, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
?
additional information
?
-
-
enzyme does not reduce prostaglandins D2 and E2
-
-
?
additional information
?
-
-
enzyme does not reduce prostaglandins D2 and E2
-
-
?
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(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
(5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
prostaglandin D2 + NADP+
9alpha,11beta-prostaglandin F2 + NADPH
-
-
-
?
prostaglandin D2 + NADPH + H+
9-alpha,11-beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2alphabeta + NADP+
-
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
prostaglandin H2 + NADPH + H+
9alpha,11alpha-prostaglandin F2alpha + NADP+
-
-
-
?
prostaglandin H2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
additional information
?
-
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH + H+
-
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
transformation of endogenous prostaglandin D2 to prostaglandin F2alpha
-
-
?
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH
(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+
-
prostaglandin F2alpha exhibits contraction of smooth muscles in the uterus, brochus trachea, luteolysis, the initiation of partutition and pain transmission
-
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
product is involved in bronchial, vascular, and arterial smooth muscle contraction, product inhibits platelet aggregation and activates urinary excretion
-
?
prostaglandin D2 + NADPH + H+
prostaglandin 9alpha,11beta-F2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
?
prostaglandin H2 + NADP+
prostaglandin F2alpha + NADPH + H+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin D2 + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
enzyme also shows PGH2 9-,11-endoperoxide reductase activity
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
prostaglandin H2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
?
additional information
?
-
-
the enzyme is important for the production of lyteolytic prostaglandin F2alpha in the endometrium of cows, regulatory mechanisms, overview
-
-
?
additional information
?
-
-
the cytosolic enzyme synergistically interacts with cyclooxygenase 1 and 2, coupling, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
?
additional information
?
-
-
the enzyme has dual activity as PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase
-
-
?
additional information
?
-
the enzyme has dual activity as PGD2 11-ketoreductase and PGH2 9,11-endoperoxide reductase
-
-
?
additional information
?
-
AKR1C3 is overexpressed in keloids and mediates the conversion of PGD2 to 9alpha,11beta-PGF2 in keloid and normal fibroblasts
-
-
?
additional information
?
-
-
coupling ability between cyclooxygenase COX-2 and the prostanoid synthases performing the last stepes in the biosynthesis of prostaglandins PGE2, PGD2, PGF2alpha, and PGI2, regulation, overview, the 20alpha-hydroxysteroid dehydrogenase also shows prostaglandin F synthase activity in the endometrium during luteolysis
-
-
?
additional information
?
-
-
prostaglandin F synthase and prostaglandin F receptor are involved in the control of testosterone release from Leydig cells and in spermatogenesis via the local pathway and the hypothalamo-hypophysial-testis-pathway
-
-
?
additional information
?
-
-
enzyme interacts with cyclooxygenase 1 and 2, isozyme PGFS-I interacts predominantly with cyclooxygenase 2, i.e. COX-2
-
-
?
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(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
bimatoprost
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
ONO1370
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
ONO1349
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
ONO1373
(Z)-7-[(1R,4S,5S,6R)-((E)-6-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity
(Z)-7-[(1R,4S,5S,6R)-2-methyl-6-((E)-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity, competitive, binds to the active site
(Z)-7-[(1R,4S,5S,6R)-6-((E)-(S)-3-hydroxy-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
-
15-deoxy-DELTA12,14-prostaglandin J2
15d-PGJ2, the enzyme inhibitor attenuates proliferation, inhibits collagen gel contraction and induces activation of the apoptotic marker, caspase-3, in CRL1762 keloid fibroblasts
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)-N-((trifluoromethyl)sulfonyl)acetamide
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
540fold selectivity for isoform AKR1C3 over isoform AKR1C2
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
4-carboxy-2',4'-dinitrodiphenylamine
-
4-carboxy-2-aminodiphenylamine
-
4-chloro-N-(4-tolyl)-anthranilic acid
-
4-chloro-N-phenylanthranilic acid
-
4-nitro-N-phenylanthranilic acid
-
4-nitrobenzaldehyde
-
competitive inhibition of PGD2 but not of PGH2 reduction
5-methyl-N-phenylanthranilic acid
-
acetate
occupies the oxyanion hole of the active site, 2 complex structures
AgNO3
-
at 0.05 mM 87-100% inhibition, depending on the substrate
CdSO4
-
at 5 mM 91-100% inhibition, depending on the substrate
CuSO4
-
at 5 mM 93-96% inhibition, depending on the substrate; the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
HgCl2
-
at 1 mM 94-100% inhibition, depending on the substrate; IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
indomethacin methyl ester
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3
N-(4-chlorobenzoyl)-melatonin
ponalrestat
specific inhibitor developed to block AKR1B1 activity. Application reduces prostaglandin F2alpha production in response to interleukin IL-1beta in both cultured endometrial cells and endometrial explants
rutin
binding structure at the substrate binding site
tert-butyl hydroperoxide
-
ZnSO4
-
at 5 mM 71-100% inhibition, depending on the substrate
9,10-phenanthrenequinone
-
competitive inhibition of PGD2 but not of PGH2 reduction; competitive inhibitor of the reduction of prostaglandin D2, not of prostaglandin H2
9,10-phenanthrenequinone
-
9,10-phenanthrenequinone
the prostaglandin D2 11-ketoreductase activity of PGFS is competitively inhibited by 9,10-phenanthrenequinone
9,10-phenanthrenequinone
-
9,10-phenanthrenequinone
-
competitive inhibition of the PGD2 11-ketoreductase activity, not of PGH2 9-,11-endoperoxide reductase activity
bimatoprost
ethyl amide analogue of 17-phenyl-trinor PGF2alpha, inhibits all enzyme activities noncompetitively at low concentration, binds to a site different from the active site; potent inhibitor
bimatoprost
inhibits the prostaglandin D2 11-ketoreductase activity as well as the prostaglandin H2 9,11-endoperoxide reductase activity of PGFS
Flufenamic acid
nonsteroidal anti-inflammatory drug, binds to both the active site and the beta-hairpin loop at the opposite end of the central beta-barrel, complex structure
flurbiprofen
-
Ibuprofen
-
indomethacin
nonsteroidal anti-inflammatory drug, 1 molecule binds to the active site, complex structure
indomethacin
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3
indomethacin
inhibits AKR1C3, but does not inhibit highly related AKR1C1 or AKR1C2
indomethacin
-
at 0.005 mg/ml in vivo inhibition of prostaglandin formation
interferon tau
-
recombinant ovine interferon tau down-regulates mRNA gene expression of the prostaglandin F synthase at a concentration of 0.000001 mg/ml
-
interferon tau
-
recombinant bovine interferon tau down-regulates mRNA gene expression of the prostaglandin F synthase after stimulation with oxytocin
-
Meclofenamic acid
-
methylglyoxal
-
N-(4-chlorobenzoyl)-melatonin
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3, not inhibitory to cyclooxygenases. Uncompetitive versus 9,10-phenynthrenequinone, competitive versus DELTA4-andostene-3,17-dione
N-(4-chlorobenzoyl)-melatonin
exhibits uncompetitive inhibition patterns for the reduction of 9,10-phenanthrenequinone but competitive inhibition patterns for the reduction of androstenedione by AKR1C3
naproxen
-
sorbinil
-
sorbinil
-
significantly inhibits the prostaglandin F2alpha synthase activity of AKR1B3 in a non-competitive fashion, whereas AKR1B7 is not sensitive to the inhibitor
sulindac
-
Tolrestat
inhibition of all 3 enzyme activities, most effective inhibiting the PGD2 11-ketoreductase activity
Tolrestat
-
significantly inhibits the prostaglandin F2alpha synthase activity of AKR1B3 in a non-competitive fashion, whereas AKR1B7 is not sensitive to the inhibitor
Zomepirac
-
additional information
-
AKR1C3 is potently inhibited by non-steroidal anti-inflammatory drugs, which are protective against breast cancer
-
additional information
AKR1C3 is potently inhibited by non-steroidal anti-inflammatory drugs, which are protective against breast cancer
-
additional information
heat treatment of AKR1B1 at 100°C for 5 min completely inactivates the prostaglandin F2alpha synthase activity, which is strictly dependent on the presence of NADPH
-
additional information
heat treatment of AKR1B1 at 100°C for 5 min completely inactivates the prostaglandin F2alpha synthase activity, which is strictly dependent on the presence of NADPH
-
additional information
-
heat treatment of AKR1B1 at 100°C for 5 min completely inactivates the prostaglandin F2alpha synthase activity, which is strictly dependent on the presence of NADPH
-
additional information
inhibitors such as alrestatin, ponalrestat, and EBPC exhibit distinct and characteristic inhibition of prostaglandin F2alpha production in different cell models
-
additional information
-
inhibitors such as alrestatin, ponalrestat, and EBPC exhibit distinct and characteristic inhibition of prostaglandin F2alpha production in different cell models
-
additional information
combination of indomethacin with tert-butyl hydroperoxide significantly inhibits the growth of radiation-resistant AKR1C3-over cells
-
additional information
-
heat treatment of AKR1B3 and AKR1B7 at 100°C for 5 min completely inactivates the prostaglandin F2alpha synthase activities, which is strictly dependent on the presence of NADPH
-
additional information
less than 10% inhibition at 0.05 mM: phenolphthalein, hexestrol, medroxyprogesterone acetate, progesterone, testosterone, cortisol, dehydroepiandrosterone
-
additional information
-
less than 10% inhibition at 0.05 mM: phenolphthalein, hexestrol, medroxyprogesterone acetate, progesterone, testosterone, cortisol, dehydroepiandrosterone
-
additional information
-
no inhibition by 9,10-phenanthrenequinone
-
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0.005 - 0.06
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
0.3 - 1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.13 - 1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.06 - 1
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
0.052
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
Homo sapiens
pH 7.0, 37°C
0.00021
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl )-N-((trifluoromethyl)sulfonyl)acetamide
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.00009
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.00022
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.002
4-benzoyl-benzoic acid
Homo sapiens
-
0.0004
4-carboxy-2',4'-dinitrodiphenylamine
Homo sapiens
-
0.011
4-carboxy-2-aminodiphenylamine
Homo sapiens
-
0.0015
4-chloro-N-(4-tolyl)-anthranilic acid
Homo sapiens
-
0.003
4-chloro-N-phenylanthranilic acid
Homo sapiens
-
0.002
4-nitro-N-phenylanthranilic acid
Homo sapiens
-
0.011
5-methyl-N-phenylanthranilic acid
Homo sapiens
-
0.005
Ag+
Bos taurus
-
IC50 = 0.005 mM
1.2
aspirin
Homo sapiens
-
0.018
benzbromarone
Mus musculus
wild-type, pH 7, 37°C
0.95
Cd2+
Bos taurus
-
IC50 = 0.95 mM
0.4
Cu2+
Bos taurus
-
IC50 = 0.4 mM
0.0087
estradiol
Mus musculus
wild-type, pH 7, 37°C
0.037
Ethacrynic acid
Mus musculus
wild-type, pH 7, 37°C
0.054
Flufenamic acid
Mus musculus
wild-type, pH 7, 37°C
0.3
HgCl2
Bos taurus
-
IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
0.0023
indomethacin methyl ester
Homo sapiens
pH 7.0, 37°C
0.00039
Mefenamic acid
Homo sapiens
-
0.0078
N-(4-chlorobenzoyl)-melatonin
Homo sapiens
pH 7.0, 37°C
0.014
quercetin
Mus musculus
wild-type, pH 7, 37°C
0.77
salicylic acid
Homo sapiens
-
1.4
Zn2+
Bos taurus
-
IC50 = 1.4 mM
0.005
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
Homo sapiens
recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.006
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.06
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
Homo sapiens
recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.3
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.13
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.06
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
IC50 about 1 mM, recombinant enzyme, using prostaglandin D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
Homo sapiens
IC50 about 1 mM, recombinant enzyme, using prostamide D2 as substrate, in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.005
bimatoprost
Homo sapiens
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.006
bimatoprost
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.06
bimatoprost
Homo sapiens
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.0078
flurbiprofen
Homo sapiens
-
0.0078
flurbiprofen
Homo sapiens
pH 7.0, 37°C
0.0099
Ibuprofen
Homo sapiens
-
0.0099
Ibuprofen
Homo sapiens
pH 7.0, 37°C
0.0023
indomethacin
Homo sapiens
-
0.0023
indomethacin
Homo sapiens
pH 7.0, 37°C
0.0007
Meclofenamic acid
Homo sapiens
-
0.0007
Meclofenamic acid
Homo sapiens
pH 7.0, 37°C
0.0014
naproxen
Homo sapiens
-
0.0014
naproxen
Homo sapiens
pH 7.0, 37°C
0.13
ONO1349
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
ONO1349
Homo sapiens
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
ONO1349
Homo sapiens
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.3
ONO1370
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
ONO1370
Homo sapiens
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
ONO1370
Homo sapiens
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.06
ONO1373
Homo sapiens
recombinant enzyme, using prostaglandin H2 2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
ONO1373
Homo sapiens
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
1
ONO1373
Homo sapiens
recombinant enzyme, using prostamide D2 2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.0034
sulindac
Homo sapiens
-
0.0034
sulindac
Homo sapiens
pH 7.0, 37°C
0.1
Tolrestat
Homo sapiens
recombinant enzyme, using prostaglandin D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.3
Tolrestat
Homo sapiens
recombinant enzyme, using prostaglandin H2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.45
Tolrestat
Homo sapiens
recombinant enzyme, using prostamide D2 as substrate,in 0.1 M potassium phosphate buffer, pH 6.5, at 37°C
0.04
Zomepirac
Homo sapiens
-
0.04
Zomepirac
Homo sapiens
pH 7.0, 37°C
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evolution
most prostaglandin F2alpha synthases (PGFS) identified to date are aldo-ketoreductases, AKRs
evolution
the enzyme belongs to the aldo-keto reductase family 1
malfunction
administration of an AKR1C3 inhibitor significantly decreases 11beta-PGF2alpha concentrations in culture media of breast cancer cells
malfunction
although attenuating AKR1C3 expression in squamous cell carcinoma cells by siRNA does not affect growth, treatment with PGD2 and its dehydration metabolite, 15delta-PGJ2, decreases squamous cell carcinoma, SCC, proliferation in a PPARgamma-dependent manner. In addition, treatment with the PPARgamma agonist pioglitazone profoundly inhibits squamous cell carcinoma proliferation. SCC-AKR1C3 metabolizes protaglandin D2, PGD2, to 9alpha,11beta-prostaglandin F2 12fold faster than the parent cell line and is protected from the antiproliferative effect mediated by PGD2. PGD2 and its metabolite 15delta-prostaglandin J2 attenuate SCC proliferation in a PPARgamma-dependent manner, therefore activation of PPARgamma by agonists such as pioglitazone may benefit those at high risk of SCC
malfunction
the enzyme inhibitor 15-deoxy-delta12,14-prostaglandin J2 attenuates proliferation, inhibits collagen gel contraction and induces activation of the apoptotic marker, caspase-3, in CRL1762 keloid fibroblasts, overview
metabolism
AKR1B1 is able to produce PGF2alpha in the endometrium in addition toAKR1C3. The PGF synthase activity of AKR1B1 proves to be much higher than that of AKR1C3
metabolism
AKR1B1 is involved in the synthesis of PGF2alpha. Pathways of prostaglandin F2alpha biosynthesis in human cells, overview
metabolism
AKR1C3 is able to produce PGF2alpha in the endometrium in addition to AKR1B1. The PGF synthase activity of AKR1B1 proves to be much higher than that of AKR1C3
metabolism
AKR1C3 is an enzyme responsible for the metabolism of steroid hormones such as androgens, progesterones and estrogens in addition to the reduction of PGD2 to 11beta-PGF2alpha
metabolism
availability of prostaglandins can be regulated by changes in 15-hydroxyprostaglandin dehydrogenase, HPGD, an enzyme that catabolizes prostaglandin E2 and prostaglandin F2alpha to their inactive metabolites 13,14-dihydro-15keto-PGF2alpha and 13,14-dihydro-15-keto prostaglandin E2 (PGEM)
metabolism
enzyme PGF is involved in essential lipid metabolism pathways
metabolism
enzyme PGF is involved in essential lipid metabolism pathways
metabolism
the prostaglandin H2 (PGH2) is the common precursor of prostaglandin F2alpha (PGF2alphha) and prostaglandin E2 (PGE2). PGH2 is converted into one of the active prostaglandins by a specific terminal synthase, such as PGE2 synthase (PGES), which is responsible for PGE2 production or 9,11-endoperoxidase reductase, which has PGF2alpha synthase (PGFS) activity
metabolism
there are three different pathways for the synthesis of the uterotonic PGF2alpha: 1. from PGH2 by PGH 9-,11-endoperoxide reductase, 2. from PGD2 by PGD 11-ketoreductase, 3. from PGE2 by PGE 9-ketoreductase
metabolism
-
enzyme PGF is involved in essential lipid metabolism pathways
-
physiological function
-
prostamide/PGF synthase may play an important functional role in the central nervous system
physiological function
prostamide/PGF synthase may play an important functional role in the central nervous system. It directly synthesizes prostamide/PGF2alpha from prostamide/PGH2 better than PGF synthase
physiological function
-
knock-down by small interfering RNA for Akr1b3 suppresses PGF2 production and enhances the expression of adipogenic genes such as peroxisome proliferator-activated receptor gamma, fatty acid-binding protein 4, and stearoyl-CoA desaturase
physiological function
AKR1C3 is overexpressed in skin squamous cell carcinoma (SCC) and affects SCC growth via prostaglandin metabolism. AKR1C3 is overexpressed in various malignancies, suggesting a tumor promoting function. SCC-AKR1C3 metabolizes protaglandin D2, PGD2, to 9alpha,11beta prostaglandin F2. Unlike other AKR1C members, AKR1C3 can synthesize prostaglandin F2alpha from prostaglandin H2, an arachidonic acid derivative synthesized by cyclooxygenase
physiological function
in breast cancer, the status of the 11alpha-PGF2alpha and 11beta-PGF2alpha cognate FP receptor is associated with adverse clinical outcome only in the AKR1C3 positive cases, immunohistochemical analysis. FP receptor-mediated functions of 11beta-PGF2alpha using FP receptor expressed MCF-7 cell line shows that 11beta-PGF2alpha treatment phosphorylates ERK and CREB and induces Slug expression through FP receptor in MCF-FP, and MCF-FP cells demonstrate decreased chemosensitivity compared to parental controls. The actions of AKR1C3, but not of AKR1B1, can produce FP receptor ligands whose activation results in carcinoma cell survival in breast cancer. 11beta-PGF2alpha stimulates phosphorylation of ERK and CREB via FP receptor. AKR1C3-dependent signaling performs through 11beta-PGF2alpha and the FP receptor, overview
physiological function
in breast cancer, the status of the 11alpha-PGF2alpha and 11beta-PGF2alpha cognate FP receptor is associated with adverse clinical outcome only in the AKR1C3 positive cases, while there are no significant correlations between FP receptor status and any of the clinicathological parameters in AKR1B1 positive cases. AKR1B1 does not induce Slug expression
physiological function
-
lentiviral vector-mediated delivery of the prostaglandin F synthase (PGFS) gene resultes in long-term reduction of intraocular pressure and may eliminate off-target tissue effects and the need for daily topical PGF2alpha self-administration
physiological function
PGF2alpha plays important roles in the regulation of ocular pressure, renal absorption, cardiovascular function, adipocyte differentiation, and female reproductive function. Role of AKR1C3 in the formation of PGF2alpha from PGH2 in the bovine endometrium
physiological function
PGF2alpha plays important roles in the regulation of ocular pressure, renal absorption, cardiovascular function, adipocyte differentiation, and female reproductive function. Role of bovine AKR1B1, previously known as AKR1B5, in the formation of PGF2alpha from PGH2 in the bovine endometrium
physiological function
-
prostaglandin F2alpha is the main luteolytic factor in pigs and its biosynthesis is catalyzed by prostaglandin F2alpha synthase, PGFS. The enzyme acts via specific seven-transmembrane G protein-coupled receptor (PTGFR) localized in large luteal cells. Intraluteal action of PGF2alpha causes a decrease in steroidogenic capacity and diminished production of progesterone. Intraluteal production of PGF2a is considered to be an important part of the luteolytic machinery
physiological function
prostaglandins (PGs) are important regulators of female reproductive function. The primary PGs produced in the endometrium are PGE2 and PGF2alpha. Role of aldo-ketoreductase (AKR)1B1 in increased PGF2alpha production by human endometrial cells following stimulation with interleukin-1beta (IL-1beta)
physiological function
the enzyme is involved in prostaglandins metabolism. The produced PGF2alpha can not only promote prostate cancer cell's proliferation but also enhance prostate cancer cells resistance to radition. Overexpression of AKR1C3 significantly enhances human prostate cancer cells PCa resistance to radiation (or tert-butyl hydroperoxide) through activation of MAPK pathway. AKR1C3 has a pivotal role in the radioresistance of esophageal cancer and non-small-cell lung cancer
physiological function
The major eicosanoid secreted by mast cells is prostaglandin D2 (PGD2), a relatively unstable pro-inflammatory mediator which can be spontaneously converted to 15-deoxy-(Delta12,14)-prostaglandin J2(15d-PGJ2) or enzymatically metabolized to 9alpha,11beta-PGF2 by aldo-keto reductase 1C3 (AKR1C3). Role of enzyme AKR1C3-mediated prostaglandin D2 (PGD2) metabolism in keloids, overview. Keloids are progressively expanding scars, mostly prevalent in individuals of African descent. Metabolism of PGD2 to 9a,11b-PGF2 by both, keloids and normal fibroblasts, is dependent on AKR1C3
physiological function
the utero/placental expression of PGFS (AKR1C3) is identified in the superficial uterine glands throughout gestation and in the trophoblast cells within the feto-maternal contact zone during placentation, suggesting a possible role for PGFS (AKR1C3) in the trophoblast invasion
physiological function
overexpression of PGF2S leads to an increase of infectivity in vitro
physiological function
parasites overexpressing PGFS show alteration of enzymes associated with oxidative stress protection such as superoxide dismutase A and trypanothione reductase. Transfected parasites are approximately 2 times more susceptible to benznidazole and 10 times more susceptible to H2O2, and to genetic damage and oxidative stress. Transfected parasites are less infective than wild-type parasites and they show higher alteration in mitochondrial membrane potential and cell cycle after treatment with benznidazole
physiological function
PGFS overexpressing parasites are less able to complete the infective cycle in cell culture infections and increase cardiac tissue parasitic load in infected mice. Parasites overexpressing the enzyme increase PGF2alpha synthesis from arachidonic acid and display increased susceptibility to benznidazole and nifurtimox but increased resistance to hydrogen peroxide
physiological function
-
overexpression of PGF2S leads to an increase of infectivity in vitro
-
physiological function
-
PGFS overexpressing parasites are less able to complete the infective cycle in cell culture infections and increase cardiac tissue parasitic load in infected mice. Parasites overexpressing the enzyme increase PGF2alpha synthesis from arachidonic acid and display increased susceptibility to benznidazole and nifurtimox but increased resistance to hydrogen peroxide
-
physiological function
-
parasites overexpressing PGFS show alteration of enzymes associated with oxidative stress protection such as superoxide dismutase A and trypanothione reductase. Transfected parasites are approximately 2 times more susceptible to benznidazole and 10 times more susceptible to H2O2, and to genetic damage and oxidative stress. Transfected parasites are less infective than wild-type parasites and they show higher alteration in mitochondrial membrane potential and cell cycle after treatment with benznidazole
-
physiological function
-
prostaglandin F2alpha is the main luteolytic factor in pigs and its biosynthesis is catalyzed by prostaglandin F2alpha synthase, PGFS. The enzyme acts via specific seven-transmembrane G protein-coupled receptor (PTGFR) localized in large luteal cells. Intraluteal action of PGF2alpha causes a decrease in steroidogenic capacity and diminished production of progesterone. Intraluteal production of PGF2a is considered to be an important part of the luteolytic machinery
-
additional information
a loop with residues 188-196 in TrcrA.00019.a.B1 shows significant movement between the apoenzyme and holoenzyme. The Trypanosoma cruzi loop becomes ordered and a key interaction with one of the phosphates of NADP at Ser193 is likely to stabilize this region
additional information
-
a loop with residues 188-196 in TrcrA.00019.a.B1 shows significant movement between the apoenzyme and holoenzyme. The Trypanosoma cruzi loop becomes ordered and a key interaction with one of the phosphates of NADP at Ser193 is likely to stabilize this region
additional information
a loop with residues 201-205 (disordered) in LemaA.00019.a.B1 shows significant movement between the apoenzyme and holoenzyme. The Leishmania major loop becomes ordered and a key interaction with one of the phosphates of NADP at Gln202 is likely to stabilize this region
additional information
-
a loop with residues 201-205 (disordered) in LemaA.00019.a.B1 shows significant movement between the apoenzyme and holoenzyme. The Leishmania major loop becomes ordered and a key interaction with one of the phosphates of NADP at Gln202 is likely to stabilize this region
additional information
comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
additional information
-
comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
additional information
comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
additional information
-
comparisons of PGFS activity of recombinant bovine and human endometrial AKRs, overview
additional information
-
a loop with residues 188-196 in TrcrA.00019.a.B1 shows significant movement between the apoenzyme and holoenzyme. The Trypanosoma cruzi loop becomes ordered and a key interaction with one of the phosphates of NADP at Ser193 is likely to stabilize this region
-
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Endo, K.; Fukui, M.; Mishima, M.; Watanabe, K.
Metabolism of vitamin A affected by prostaglandin F synthase in contractile interstitial cells of bovine lung
Biochem. Biophys. Res. Commun.
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Bos taurus
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Bos taurus, Rana temporaria
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659
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Oryctolagus cuniculus
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-
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cDNA cloning and mutagenesis study of liver-type prostaglandin F synthase, and identification of the prostaglandin F producing cells in the liver
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507
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424
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Homo sapiens, Homo sapiens (P42330)
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Komoto, J.; Yamada, T.; Watanabe, K.; Takusagawa, F.
Crystal structure of human prostaglandin F synthase (AKR1C3)
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43
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2004
Homo sapiens (P42330), Homo sapiens
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Nakashima, K.; Ueno, N.; Kamei, D.; Tanioka, T.; Nakatani, Y.; Murakami, M.; Kudo, I.
Coupling between cyclooxygenases and prostaglandin F(2alpha) synthase. Detection of an inducible, glutathione-activated, membrane-bound prostaglandin F2alpha-synthetic activity
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Homo sapiens, Mus musculus, Rattus norvegicus
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Immunocytochemical localization of prostaglandin F synthase II in the rat spinal cord
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969
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Rattus norvegicus
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Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin
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Homo sapiens (P42330)
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Crystallization and preliminary X-ray crystallographic studies of Trypanosoma brucei prostaglandin F2 alpha synthase
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Watanabe, K.
Prostaglandin F synthase
Prostaglandins
68-69
401-407
2002
Bos taurus, Oryctolagus cuniculus, Ovis aries, Homo sapiens, Rattus norvegicus, Trypanosoma brucei
brenda
Franczak, A.; Woclawek-Potocka, I.; Oponowicz, A.; Kurowicka, B.; Kotwica, G.
Oxytocin stimulates prostaglandin F2alpha secretion and prostaglandin F synthase protein expression in porcine myometrial tissue
Reprod. Biol.
4
177-184
2004
Sus scrofa
brenda
Waclawik, A.; Rivero-Muller, A.; Blitek, A.; Kaczmarek, M.M.; Brokken, L.J.; Watanabe, K.; Rahman, N.A.; Ziecik, A.J.
Molecular cloning and spatiotemporal expression of prostaglandin F synthase and microsomal prostaglandin E synthase-1 in porcine endometrium
Endocrinology
147
210-221
2006
Sus scrofa (Q2TJA5), Sus scrofa
brenda
Ueno, N.; Takegoshi, Y.; Kamei, D.; Kudo, I.; Murakami, M.
Coupling between cyclooxygenases and terminal prostanoid synthases
Biochem. Biophys. Res. Commun.
338
70-76
2005
Mus musculus
brenda
Sakurai, M.; Oishi, K.; Watanabe, K.
Localization of cyclooxygenases-1 and -2, and prostaglandin F synthase in human kidney and renal cell carcinoma
Biochem. Biophys. Res. Commun.
338
82-86
2005
Homo sapiens
brenda
Komoto, J.; Yamada, T.; Watanabe, K.; Woodward, D.F.; Takusagawa, F.
Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase (PGFS): crystal structure of PGFS containing bimatoprost
Biochemistry
45
1987-1996
2006
Homo sapiens, Homo sapiens (P42330)
brenda
Yang, W.; Ni, J.; Woodward, D.F.; Tang-Liu, D.D.; Ling, K.H.
Enzymatic formation of prostamide F2alpha from anandamide involves a newly identified intermediate metabolite, prostamide H2
J. Lipid Res.
46
2745-2751
2005
Homo sapiens
brenda
Schuler, G.; Teichmann, U.; Kowalewski, M.P.; Hoffmann, B.; Madore, E.; Fortier, M.A.; Klisch, K.
Expression of cyclooxygenase-II (COX-II) and 20alpha-hydroxysteroid dehydrogenase (20alpha-HSD)/prostaglandin F-synthase (PGFS) in bovine placentomes: implications for the initiation of parturition in cattle
Placenta
27
1022-1029
2006
Bos taurus
brenda
Kowalewski, M.P.; Mutembei, H.M.; Hoffmann, B.
Canine prostaglandin F2alpha receptor (FP) and prostaglandin F2alpha synthase (PGFS): Molecular cloning and expression in the corpus luteum
Anim. Reprod. Sci.
107
161-175
2008
Canis lupus familiaris (Q5FYA7), Canis lupus familiaris
brenda
Byrns, M.C.; Steckelbroeck, S.; Penning, T.M.
An indomethacin analogue, N-(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies
Biochem. Pharmacol.
75
484-493
2008
Homo sapiens (P42330)
brenda
Suzuki-Yamamoto, T.; Sugimoto, Y.; Ichikawa, A.; Ishimura, K.
Co-localization of prostaglandin F synthase, cyclooxygenase-1 and prostaglandin F receptor in mouse Leydig cells
Histochem. Cell Biol.
128
317-322
2007
Mus musculus
brenda
Moriuchi, H.; Koda, N.; Okuda-Ashitaka, E.; Daiyasu, H.; Ogasawara, K.; Toh, H.; Ito, S.; Woodward, D.F.; Watanabe, K.
Molecular characterization of a novel type of prostamide/prostaglandin F synthase, belonging to the thioredoxin-like superfamily
J. Biol. Chem.
283
792-801
2008
Mus musculus, Sus scrofa (A9CQL8), Sus scrofa
brenda
Waclawik, A.; Ziecik, A.J.
Differential expression of prostaglandin (PG) synthesis enzymes in conceptus during peri-implantation period and endometrial expression of carbonyl reductase/PG 9-ketoreductase in the pig
J. Endocrinol.
194
499-510
2007
Sus scrofa
brenda
Wasielak, M.; Glowacz, M.; Kaminska, K.; Waclawik, A.; Bogacki, M.
The influence of embryo presence on prostaglandins synthesis and prostaglandin E2 and F2alpha content in corpora lutea during periimplantation period in the pig
Mol. Reprod. Dev.
75
1208-1216
2008
Sus scrofa
brenda
Dozier, B.L.; Watanabe, K.; Duffy, D.M.
Two pathways for prostaglandin F2 alpha synthesis by the primate periovulatory follicle
Reproduction
136
53-63
2008
Macaca fascicularis, Homo sapiens (P42330), Homo sapiens AKR1C3 (P42330), Macaca fascicularis AKR1C3
brenda
Byrns, M.; Penning, T.
Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): Role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs
Chem. Biol. Interact.
178
221-227
2009
Homo sapiens, Homo sapiens (P42330)
brenda
Inagaki, S.; Esaka, Y.; Deyashiki, Y.; Uno, B.; Hara, A.; Toyooka, T.
Human liver dihydrodiol dehydrogenase 1-catalyzed reaction generating 9alpha,11beta-prostaglandin F2 from prostaglandin D2 followed by micellar electrokinetic chromatography
J. Sep. Sci.
31
735-740
2008
Homo sapiens
brenda
Kabututu, Z.; Manin, M.; Pointud, J.C.; Maruyama, T.; Nagata, N.; Lambert, S.; Lefrancois-Martinez, A.M.; Martinez, A.; Urade, Y.
Prostaglandin F2alpha synthase activities of aldo-keto reductase 1B1, 1B3 and 1B7
J. Biochem.
145
161-168
2009
Mus musculus, Homo sapiens (P15121), Homo sapiens (P42330), Homo sapiens
brenda
Suzuki-Yamamoto, T.; Toida, K.; Sugimoto, Y.; Ishimura, K.
Colocalization of prostaglandin F2alpha receptor FP and prostaglandin F synthase-I in the spinal cord
J. Lipid Res.
50
1996-2003
2009
Rattus norvegicus
brenda
Wasielak, M.; Kaminska, K.; Bogacki, M.
Effect of the conceptus on uterine prostaglandin-F2alpha and prostaglandin-E2 release and synthesis during the periimplantation period in the pig
Reprod. Fertil. Dev.
21
709-717
2009
Sus scrofa
brenda
Yoshikawa, K.; Takei, S.; Hasegawa-Ishii, S.; Chiba, Y.; Furukawa, A.; Kawamura, N.; Hosokawa, M.; Woodward, D.F.; Watanabe, K.; Shimada, A.
Preferential localization of prostamide/prostaglandin F synthase in myelin sheaths of the central nervous system
Brain Res.
1367
22-32
2011
Mus musculus
brenda
Fujimori, K.; Ueno, T.; Nagata, N.; Kashiwagi, K.; Aritake, K.; Amano, F.; Urade, Y.
Suppression of adipocyte differentiation by aldo-keto reductase 1B3 acting as prostaglandin F2alpha synthase
J. Biol. Chem.
285
8880-8886
2010
Mus musculus
brenda
Phillips, R.J.; Al-Zamil, H.; Hunt, L.P.; Fortier, M.A.; Lopez Bernal, A.
Genes for prostaglandin synthesis, transport and inactivation are differentially expressed in human uterine tissues, and the prostaglandin F synthase AKR1B1 is induced in myometrial cells by inflammatory cytokines
Mol. Hum. Reprod.
17
1-13
2011
Homo sapiens
brenda
Gram, A.; Buechler, U.; Boos, A.; Hoffmann, B.; Kowalewski, M.P.
Biosynthesis and degradation of canine placental prostaglandins: prepartum changes in expression and function of prostaglandin F2alpha-synthase (PGFS, AKR1C3) and 15-prostaglandin dehydrogenase
Biol. Reprod.
89
002
2013
Canis lupus familiaris
brenda
Nagata, N.; Kusakari, Y.; Fukunishi, Y.; Inoue, T.; Urade, Y.
Catalytic mechanism of the primary human prostaglandin F2alpha synthase, aldo-keto reductase 1B1 - prostaglandin D2 synthase activity in the absence of NADP(H)
FEBS J.
278
1288-1298
2011
Mus musculus, Homo sapiens (P15121), Homo sapiens
brenda
Bresson, E.; Lacroix-Pepin, N.; Boucher-Kovalik, S.; Chapdelaine, P.; Fortier, M.A.
The prostaglandin F synthase activity of the human aldose reductase AKR1B1 brings new lenses to look at pathologic conditions
Front. Pharmacol.
3
98
2012
Homo sapiens (P15121), Homo sapiens
brenda
Bresson, E.; Boucher-Kovalik, S.; Chapdelaine, P.; Madore, E.; Harvey, N.; Laberge, P.Y.; Leboeuf, M.; Fortier, M.A.
The human aldose reductase AKR1B1 qualifies as the primary prostaglandin F synthase in the endometrium
J. Clin. Endocrinol. Metab.
96
210-219
2011
Homo sapiens (P15121), Homo sapiens
brenda
Liedtke, A.J.; Adeniji, A.O.; Chen, M.; Byrns, M.C.; Jin, Y.; Christianson, D.W.; Marnett, L.J.; Penning, T.M.
Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer
J. Med. Chem.
56
2429-2446
2013
Homo sapiens (P42330)
brenda
Siemieniuch, M.J.; Jursza, E.; Kowalewski, M.P.; Majewska, M.; Skarzynski, D.J.
Prostaglandin endoperoxide synthase 2 (PTGS2) and prostaglandins F2alpha and E2 synthases (PGFS and PGES) expression and prostaglandin F2alpha and E2 secretion following oestrogen and/or progesterone stimulation of the feline endometrium
Reprod. Domest. Anim.
48
72-78
2013
Felis catus (E2IGW3), Felis catus
brenda
Moen, S.O.; Fairman, J.W.; Barnes, S.R.; Sullivan, A.; Nakazawa-Hewitt, S.; Van Voorhis, W.C.; Staker, B.L.; Lorimer, D.D.; Myler, P.J.; Edwards, T.E.
Structures of prostaglandin F synthase from the protozoa Leishmania major and Trypanosoma cruzi with NADP
Acta Crystallogr. Sect. F
71
609-614
2015
Leishmania major (P22045), Leishmania major, Trypanosoma cruzi (Q4DJ07), Trypanosoma cruzi, Trypanosoma cruzi CL Brener (Q4DJ07)
brenda
Gram, A.; Buechler, U.; Boos, A.; Hoffmann, B.; Kowalewski, M.P.
Biosynthesis and degradation of canine placental prostaglandins: prepartum changes in expression and function of prostaglandin F2?-synthase (PGFS, AKR1C3) and 15-hydroxyprostaglandin dehydrogenase (HPGD)
Biol. Reprod.
89
2-2
2013
Canis lupus familiaris (Q5FYA7), Canis lupus familiaris
brenda
Lee, E.S.; Rasmussen, C.A.; Filla, M.S.; Slauson, S.R.; Kolb, A.W.; Peters, D.M.; Kaufman, P.L.; Gabelt, B.T.; Brandt, C.R.
Prospects for lentiviral vector mediated prostaglandin F synthase gene delivery in monkey eyes in vivo
Curr. Eye Res.
39
859-870
2014
Bos taurus
brenda
Grzesiak, M.; Knapczyk-Stwora, K.; Slomczynska, M.
The impact of flutamide on prostaglandin F2alpha synthase and prostaglandin F2alpha receptor expression, and prostaglandin F2alpha concentration in the porcine corpus luteum of pregnancy
Domest. Anim. Endocrinol.
59
81-89
2017
Sus scrofa, Sus scrofa Large White x Polish Landrace
brenda
Mantel, A.; Carpenter-Mendini, A.; VanBuskirk, J.; Pentland, A.P.
Aldo-keto reductase 1C3 is overexpressed in skin squamous cell carcinoma (SCC) and affects SCC growth via prostaglandin metabolism
Exp. Dermatol.
23
573-578
2014
Homo sapiens (P42330)
brenda
Mantel, A.; Newsome, A.; Thekkudan, T.; Frazier, R.; Katdare, M.
The role of aldo-keto reductase 1C3 (AKR1C3)-mediated prostaglandin D2 (PGD2) metabolism in keloids
Exp. Dermatol.
25
38-43
2016
Homo sapiens (P42330)
brenda
Alzamil, H.A.; Pawade, J.; Fortier, M.A.; Bernal, A.L.
Expression of the prostaglandin F synthase AKR1B1 and the prostaglandin transporter SLCO2A1 in human fetal membranes in relation to spontaneous term and preterm labor
Front. Physiol.
5
272
2014
Homo sapiens (P15121), Homo sapiens
brenda
Yoda, T.; Kikuchi, K.; Miki, Y.; Onodera, Y.; Hata, S.; Takagi, K.; Nakamura, Y.; Hirakawa, H.; Ishida, T.; Suzuki, T.; Ohuchi, N.; Sasano, H.; McNamara, K.M.
11beta-Prostaglandin F2alpha, a bioactive metabolite catalyzed by AKR1C3, stimulates prostaglandin F receptor and induces slug expression in breast cancer
Mol. Cell. Endocrinol.
413
236-247
2015
Homo sapiens (P15121), Homo sapiens (P42330)
brenda
Lacroix Pepin, N.; Chapdelaine, P.; Rodriguez, Y.; Tremblay, J.P.; Fortier, M.A.
Generation of human endometrial knockout cell lines with the CRISPR/Cas9 system confirms the prostaglandin F2alpha synthase activity of aldo-ketoreductase 1B1
Mol. Hum. Reprod.
20
650-663
2014
Homo sapiens (P15121), Homo sapiens
brenda
Sun, S.Q.; Gu, X.; Gao, X.S.; Li, Y.; Yu, H.; Xiong, W.; Yu, H.; Wang, W.; Li, Y.; Teng, Y.; Zhou, D.
Overexpression of AKR1C3 significantly enhances human prostate cancer cells resistance to radiation
Oncotarget
7
48050-48058
2016
Homo sapiens (P42330)
brenda
Lacroix Pepin, N.; Chapdelaine, P.; Fortier, M.A.
Evaluation of the prostaglandin F synthase activity of human and bovine aldo-keto reductases: AKR1A1s complement AKR1B1s as potent PGF synthases
Prostaglandins Other Lipid Mediat.
106
124-132
2013
Homo sapiens (P15121), Homo sapiens, Bos taurus (P16116), Bos taurus
brenda
Janowski, T.; Baranski, W.; Lukasik, K.; Skarzynski, D.; Zdunczyk, S.; Malinowska, K.
Endometrial mRNA expression of prostaglandin synthase enzymes PTGS 2, PTGFS and mPTGES 1 in repeat-breeding cows with cytologically determined endometritis
Acta Vet. Hung.
65
96-104
2017
Bos taurus
brenda
Endo, S.; Matsunaga, T.; Hara, A.
Mouse Akr1cl gene product is a prostaglandin D2 11-ketoreductase with strict substrate specificity
Arch. Biochem. Biophys.
674
108096
2019
Mus musculus (Q9D5U2), Mus musculus
brenda
Diaz-Viraque, F.; Chiribao, M.L.; Trochine, A.; Gonzalez-Herrera, F.; Castillo, C.; Liempi, A.; Kemmerling, U.; Maya, J.D.; Robello, C.
Old yellow enzyme from Trypanosoma cruzi exhibits in vivo prostaglandin F2alpha synthase activity and has a key role in parasite infection and drug susceptibility
Front. Immunol.
9
456
2018
Trypanosoma cruzi (V5BT91), Trypanosoma cruzi Dm28c (V5BT91)
brenda
Alves-Ferreira, E.V.C.; Ferreira, T.R.; Walrad, P.; Kaye, P.M.; Cruz, A.K.
Leishmania braziliensis prostaglandin F2alpha synthase impacts host infection
Parasit. Vectors
13
009
2020
Leishmania braziliensis (A0A3P3ZE14), Leishmania braziliensis, Leishmania braziliensis MHOM/BR/75/M2904 (A0A3P3ZE14)
brenda
Garcia-Huertas, P.; Mejia-Jaramillo, A.M.; Machado, C.R.; Guimaraes, A.C.; Triana-Chavez, O.
Prostaglandin F2alpha synthase in Trypanosoma cruzi plays critical roles in oxidative stress and susceptibility to benznidazole
R. Soc. Open Sci.
4
170773
2017
Trypanosoma cruzi (Q4E4V7), Trypanosoma cruzi CL Brener (Q4E4V7)
brenda
Dong, Z.; Zhang, N.; Mao, W.; Liu, B.; Huang, N.; Li, P.; Li, C.; Cao, J.
Kinetic effect of oestrogen on secretion of prostaglandins E2 and F2alpha in bovine oviduct epithelial cells
Reprod. Fertil. Dev.
29
482-489
2017
Bos taurus
brenda