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Literature summary for 1.1.1.188 extracted from
- Purification and characterization of prostaglandin F synthase from bovine liver (1992), Arch. Biochem. Biophys., 296, 17-26.
Activating Compound
| Activating Compound | Comment | Organism | Structure |
|---|---|---|---|
| chloride | stimulates the reduction of prostaglandin D2 and carbonyl compounds, but had no effect on prostaglandin H2 reduction | Bos taurus |  |
| NaBr | stimulates prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| NaCl | stimulates prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| NaI | stimulates prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| piroxicam | - |
Bos taurus | |
| warfarin | - |
Bos taurus | |
General Stability
| General Stability | Organism |
|---|---|
| activity is reduced less than 20% after freezing and thawing several times | Bos taurus |
| several freezing and thawing cycles reduce the activity of stored purified liver-type isozyme by 50% | Bos taurus |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 4-nitrobenzaldehyde | competitive inhibition of PGD2 but not of PGH2 reduction | Bos taurus | |
| 9,10-phenanthrenequinone | competitive inhibition of PGD2 but not of PGH2 reduction; competitive inhibitor of the reduction of prostaglandin D2, not of prostaglandin H2 | Bos taurus | |
| Ag+ | IC50 = 0.005 mM | Bos taurus | |
| AgNO3 | at 0.05 mM 87-100% inhibition, depending on the substrate | Bos taurus | |
| Cd2+ | IC50 = 0.95 mM | Bos taurus | |
| CdSO4 | at 5 mM 91-100% inhibition, depending on the substrate | Bos taurus | |
| Cu2+ | IC50 = 0.4 mM | Bos taurus | |
| CuSO4 | at 5 mM 93-96% inhibition, depending on the substrate; the liver-type isozyme is 2fold less sensitive than the lung-type isozyme | Bos taurus | |
| 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 | Bos taurus | |
| NaF | - |
Bos taurus | |
| Zn2+ | IC50 = 1.4 mM | Bos taurus | |
| ZnSO4 | at 5 mM 71-100% inhibition, depending on the substrate | Bos taurus | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.002 | - |
9,10-phenanthrenequinone | - |
Bos taurus | |
| 0.002 | - |
9,10-phenanthrenequinone | 37°C, liver-type isozyme | Bos taurus | |
| 0.0031 | - |
Hydrindantin | - |
Bos taurus | |
| 0.0031 | - |
Hydrindantin | 37°C, liver-type isozyme | Bos taurus | |
| 0.0056 | - |
Prostaglandin D3 | - |
Bos taurus | |
| 0.0056 | - |
Prostaglandin D3 | 37°C, liver-type isozyme | Bos taurus | |
| 0.007 | - |
prostaglandin D1 | - |
Bos taurus | |
| 0.007 | - |
prostaglandin D1 | 37°C, liver-type isozyme | Bos taurus | |
| 0.01 | - |
Prostaglandin D2 | - |
Bos taurus | |
| 0.01 | - |
Prostaglandin D2 | 37°C, liver-type isozyme | Bos taurus | |
| 0.0119 | - |
p-nitroacetophenone | - |
Bos taurus | |
| 0.0119 | - |
4-Nitroacetophenone | 37°C, liver-type isozyme | Bos taurus | |
| 0.0143 | - |
4-nitrobenzaldehyde | - |
Bos taurus | |
| 0.0143 | - |
4-nitrobenzaldehyde | 37°C, liver-type isozyme | Bos taurus | |
| 0.0167 | - |
menadione | - |
Bos taurus | |
| 0.0167 | - |
menadione | 37°C, liver-type isozyme | Bos taurus | |
| 0.0175 | - |
5beta-dihydrotestosterone | - |
Bos taurus | |
| 0.0175 | - |
5beta-dihydrotestosterone | 37°C, liver-type isozyme | Bos taurus | |
| 0.02 | - |
Phenylglyoxal | - |
Bos taurus | |
| 0.02 | - |
Phenylglyoxal | 37°C, liver-type isozyme | Bos taurus | |
| 0.025 | - |
prostaglandin H2 | - |
Bos taurus | |
| 0.025 | - |
prostaglandin H2 | 37°C, liver-type isozyme | Bos taurus | |
| 0.053 | - |
cyclohexanone | - |
Bos taurus | |
| 0.053 | - |
cyclohexanone | 37°C, liver-type isozyme | Bos taurus | |
| 0.12 | - |
Prostaglandin D2 | 37°C, lung-type isozyme | Bos taurus | |
| 0.143 | - |
DL-glyceraldehyde | - |
Bos taurus | |
| 0.143 | - |
DL-glyceraldehyde | 37°C, liver-type isozyme | Bos taurus | |
| 135 | - |
D-xylose | - |
Bos taurus | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| cytosol | liver-type isozyme | Bos taurus | 5829 | - |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| CaCl2 | activation | Bos taurus | |
| Cl- | the liver-type isozyme is 3fold more activated than the lung-type isozyme | Bos taurus | |
| MgCl2 | activation | Bos taurus | |
| NaBr | activation | Bos taurus | |
| NaCl | activation | Bos taurus | |
| NaI | activation | Bos taurus | |
Molecular Weight [Da]
| Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|
| 36000 | - |
SDS-PAGE | Bos taurus |
| 36000 | - |
liver-type isozyme, gel filtration | Bos taurus |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Bos taurus | - |
- |
- |
| Bos taurus | - |
liver-type and lung-type isozymes | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| native liver-type isozyme from liver, 342fold to homogeneity by ammonium sulfate fractionation, anion exchange and adsorption chromatography | Bos taurus |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| liver | two different active sites | Bos taurus | - |
| liver | liver-type isozyme | Bos taurus | - |
| lung | lung-type isozyme | Bos taurus | - |
Specific Activity [micromol/min/mg]
| Specific Activity Minimum [µmol/min/mg] | Specific Activity Maximum [µmol/min/mg] | Comment | Organism |
|---|---|---|---|
| additional information | - |
- |
Bos taurus |
| 0.003 | - |
prostaglandin H2 as substrate | Bos taurus |
| 0.003 | - |
purified liver-type isozyme, substrate prostaglandin H2 | Bos taurus |
| 0.008 | - |
purified liver-type isozyme, substrate prostaglandin I2 | Bos taurus |
| 0.046 | - |
prostaglandin D1 as substrate | Bos taurus |
| 0.046 | - |
purified liver-type isozyme, substrate prostaglandin D1 | Bos taurus |
| 0.065 | - |
xylose as substrate | Bos taurus |
| 0.089 | - |
prostaglandin D3 as substrate | Bos taurus |
| 0.089 | - |
purified liver-type isozyme, substrate prostaglandin D3 | Bos taurus |
| 0.095 | - |
prostaglandin D2 as substrate | Bos taurus |
| 0.095 | - |
purified liver-type isozyme, substrate prostaglandin D2 | Bos taurus |
| 0.13 | - |
5beta-dihydrotestosterone as substrate | Bos taurus |
| 0.159 | - |
cyclohexanone as substrate | Bos taurus |
| 0.167 | - |
menadione and hydrindantin as substrate | Bos taurus |
| 0.174 | - |
4-nitroacetophenone as substrate | Bos taurus |
| 0.206 | - |
DL-glyceraldehyde as substrate | Bos taurus |
| 0.207 | - |
phenylglyoxal as substrate | Bos taurus |
| 0.31 | - |
4-nitrobenzaldehyde as substrate | Bos taurus |
| 0.31 | - |
purified liver-type isozyme, substrate 4-nitrobenzaldehyde | Bos taurus |
| 0.339 | - |
9,10-phenanthrenequinone as substrate | Bos taurus |
| 0.339 | - |
purified liver-type isozyme, substrate 9,10-phenanthrenequinone | Bos taurus |
Storage Stability
| Storage Stability | Organism |
|---|---|
| -80°C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, stable for several months | Bos taurus |
| -80°C, purified liver-type isozyme at 1.5 mg/ml in 10 mM potassium phosphate, pH 7.0, stable for several months, several freezing and thawing cycles reduce the activity by 50% | Bos taurus |
| 25°C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, 80-90% activity, 1 month | Bos taurus |
| 4-23°C, purified liver-type isozyme, 1 month, 80-90% remaining activity | Bos taurus |
| 4°C, concentration 1.5 mg per ml 10 mM potassium phosphate buffer pH 7.0, 80-90% activity, 1 month | Bos taurus |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH | - |
Bos taurus | (5Z,13E)-(15S)-9alpha,11beta,15-trihydroxyprosta-5,13-dienoate + NADP+ | - |
? | |
| 4-nitroacetophenone + NADPH | high activity | Bos taurus | ? | - |
? | |
| 4-nitrobenzaldehyde + NADPH | - |
Bos taurus | 4-nitrobenzyl alcohol + NADP+ | - |
? | |
| 4-nitrobenzaldehyde + NADPH | high activity | Bos taurus | 4-nitrobenzalcohol + NADP+ | - |
? | |
| 5beta-dihydrotestosterone + NADPH | - |
Bos taurus | ? | - |
? | |
| 9,10-phenanthrenequinone + NADPH | - |
Bos taurus | ? | - |
? | |
| 9,10-phenanthrenequinone + NADPH | best substrate | Bos taurus | ? | - |
? | |
| cyclohexanone + NADPH | - |
Bos taurus | cyclohexanol + NADP+ | - |
? | |
| cyclohexanone + NADPH | high activity | Bos taurus | cyclohexanol + NADP+ | - |
? | |
| D-xylose + NADPH | - |
Bos taurus | ? | - |
? | |
| daunorubicin + NADPH | high activity | Bos taurus | ? | - |
? | |
| DL-glyceraldehyde + NADPH | - |
Bos taurus | DL-glycerol + NADP+ | - |
? | |
| duroquinone + NADPH | - |
Bos taurus | ? | - |
? | |
| hydrindantin + NADPH | - |
Bos taurus | ? | - |
? | |
| hydrindantin + NADPH | high activity | Bos taurus | ? | - |
? | |
| menadione + NADPH | - |
Bos taurus | ? | - |
? | |
| menadione + NADPH | high activity | Bos taurus | ? | - |
? | |
| 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 | Bos taurus | ? | - |
? | |
| 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 | Bos taurus | ? | - |
? | |
| n-butyraldehyde + NADPH | - |
Bos taurus | n-butanol + NADP+ | - |
? | |
| p-nitroacetophenone + NADPH | - |
Bos taurus | ? | - |
? | |
| phenylglyoxal + NADPH | - |
Bos taurus | ? | - |
? | |
| phenylglyoxal + NADPH | high activity | Bos taurus | ? | - |
? | |
| prostaglandin D1 + NADPH | - |
Bos taurus | ? | - |
? | |
| prostaglandin D2 + NADPH + H+ | - |
Bos taurus | 9alpha,11beta-prostaglandin F2 + NADP+ | - |
? | |
| prostaglandin D3 + NADPH | - |
Bos taurus | ? | - |
? | |
| prostaglandin H2 + NADPH + H+ | - |
Bos taurus | (5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate + NADP+ | - |
? | |
| prostaglandin H2 + NADPH + H+ | - |
Bos taurus | 9alpha,11alpha-prostaglandin F2alpha + NADP+ | - |
? | |
| prostaglandin I2 + NADPH | - |
Bos taurus | ? | - |
? | |
| ubiquinone-10 + NADPH | - |
Bos taurus | ? | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| monomer | 1 * 36000, SDS-PAGE | Bos taurus |
| monomer | 1 x 36000, liver-type isozyme, SDS-PAGE | Bos taurus |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| prostaglandin D2 11-ketoreductase | - |
Bos taurus |
| prostaglandin F synthase | - |
Bos taurus |
Temperature Stability [°C]
| Temperature Stability Minimum [°C] | Temperature Stability Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 100 | - |
5 min, inactivation | Bos taurus |
| 100 | - |
no reduction of prostaglandin D2 11-reductase after 5 min | Bos taurus |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 6 | 7 | - |
Bos taurus |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| NADPH | - |
Bos taurus | |
| NADPH | highly preferred cofactor | Bos taurus | |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0009 | - |
9,10-phenanthrenequinone | 37°C, liver-type isozyme, versus prostaglandin D2 | Bos taurus | |
| 0.005 | - |
AgNO3 | prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| 0.023 | - |
4-nitrobenzaldehyde | 37°C, liver-type isozyme, versus prostaglandin D2 | Bos taurus | |
| 0.3 | - |
HgCl2 | prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| 0.4 | - |
CuSO4 | prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| 0.95 | - |
CdSO4 | prostaglandin D2 11-ketoreductase activity | Bos taurus | |
| 1.4 | - |
ZnSO4 | prostaglandin D2 11-ketoreductase activity | Bos taurus | |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.005 | - |
IC50 = 0.005 mM | Bos taurus | Ag+ | |
| 0.3 | - |
IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme | Bos taurus | HgCl2 | |
| 0.4 | - |
IC50 = 0.4 mM | Bos taurus | Cu2+ | |
| 0.95 | - |
IC50 = 0.95 mM | Bos taurus | Cd2+ | |
| 1.4 | - |
IC50 = 1.4 mM | Bos taurus | Zn2+ | |
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