Eicosanoids

Prostaglandin K1 (compound 46) is a structurally modified analog of prostacyclin (prostanoid) with an EC₅₀ of 2800 nM for EP1 and a K_i of 2800 nM.

16,16-Dimethyl prostaglandin D2 is a biochemical reagent.

19(R)-Hydroxy prostaglandin A2 is a biochemical reagent.

(±)14(15)-EpEDE is a a polyunsaturated fatty acid and can be found in DCU (HY-W013989) -treated porcine coronary endothelial cells.

11-S-Hydroxyeicosatetraenoic acid (11(S)-Hydroxy-5(Z),8(Z),12(E),14(Z)-eicosatetraenoic acid) is an ester product.

(S,9E,11Z,14Z)-8-Hydroxyicosa-9,11,14-trienoic acid is an ester product.

15(R)-Hydroxy-11(Z),13(E)-eicosadienoic acid is an ester product.

5(S)-HETrE is a metabolite of the ω-6 fatty acid γ-linolenic acid. 5(S)-HETrE can be elevated in serum levels in an obesity mouse model.

11R(12S)-EET is a cis-epoxytrienoic acid (EETs) derivative that is metabolized by cytoplasmic cyclooxygenases. Studies have shown that 14(R), 15(S)-, 11(S),12(R)-, and 8(S),9(R)-EETs are metabolized at significantly higher rates than their enantiomers. Enzyme-catalyzed hydration revealed that water addition was non-regioselective for the 11,12-EET enantiomers, whereas water addition occurred primarily at the C9 position for both enantiomers of 8,9-EET. These results suggest that the metabolic properties of 11R(12S)-EET and other EET enantiomers in enzyme-catalyzed processes are significantly affected by their stereostructures.

11S(12R)-EET is a dominant enantiomer of epoxytrienoic acid (EET) that is metabolized at a higher rate in rat organs. It shows enantiomeric-dependent reaction selectivity in hydration, especially in the case of 11,12-EET, where water addition is non-regioselective, while in 8,9-EET, water addition occurs mainly at the C9 position. In addition, 11S(12R)-EET generates diol products with specific stereochemistry through enzymatic hydration reactions, which are affected by the selective recognition of epoxidases, reaction conversion rates, and substrate binding parameters.

Prostaglandin K2 (PGK2) is the 9,11-diketone formed by the oxidation of PGE2 or PGD2. Whether this compound exists biologically is uncertain; it is known to be resistant to metabolism by 15-hydroxy PGDH in vitro.

19(R)-hydroxy Prostaglandin E2 (19(R)-hydroxy PGE2) is found in the semen of primates, including man. It is a potent smooth muscle relaxant and a selective agonist for the EP2 receptor. It has an EC₅₀ value of 200 nM for relaxing cat tracheal rings which express EP2 receptors.

20-hydroxy Prostaglandin F2α (20-hydroxy PGF2α) is the ω-oxidation product of PGF2α. Cultured type II alveolar cells from pregnant rabbits metabolize exogenous PGF2α via microsomal cytochrome P450 ω-oxidation, producing 20-hydroxy PGF2α and its 15-hydroxy PGDH metabolites. Cells from male rabbits exhibit only the 15-hydroxy PGDH pathway.

2,3-Dinor-11beta-prostaglandin F2alpha (2,3-Dinor-11β-PGF2α) is a metabolite of PGD2. Urinary excretion of 2,3-Dinor-11beta-prostaglandin F2alpha is increased in patients with mast cell activation disease (MCAD) and has been used as a marker of increased PGD2 levels. 2,3-Dinor-11beta-prostaglandin F2alpha levels are also increased in the urine of patients with asthma and are positively correlated with impaired lung function.

15(S)-15-methyl Prostaglandin F2α methyl ester (15(S)-15-methyl PGF2α methyl ester) is a derivative of 15(S)-15-methyl PGF2α with increased membrane permeability. Hydrolysis of the methyl ester in vivo releases the biologically active 15(S)-15-methyl PGF2α, which is a potent uterine stimulant and abortifacient.

(±)8-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of (±)8-HEPE and 8(R)-HEPE. The ability of (±)8-HEPE to induce hatching of E. modestus and B. balanoides eggs is probably due to the presence of the 8(R) isomer within the racemic mixture.

12(R)-HEPE is a monohydroxy fatty acid synthesized from EPA by the eggs of the sea urchin, S. purpuratus.1 The biological activity of 12(R)-HEPE has not been extensively documented, but may be similar to that of 12(R)-HETE.

(±)12-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 12(S)-HEPE and 12(R)-HEPE. The biological activity of (±)12-HEPE is likely mediated by one of the individual isomers, most commonly the 12(S) isomer in mammalian systems. 12-HEPE inhibits platelet aggregation with the same potency as 12-HETE, exhibiting IC₅₀ values of 24 and 25 μM, respectively.1 These compounds are also equipotent as inhibitors of U46619-induced contraction of rat aorta (IC₅₀s=8.6-8.8 μM).

8-iso PGF3α is an isoprostane produced from the free-radical peroxidation of EPA. Little is known about the biological activity of 8-iso PGF3α. There is one report that it is inactive in a TP receptor mediated assay of human platelet shape change, where 8-iso PGF2α has an ED50 value of 1 μM.

13,14-dihydro Prostaglandin F2α (13,14-dihydro PGF2α) is the analog of PGF2α which has no unsaturation in the lower side chain. It causes luteolysis in hamsters with a potency five times higher than PGF2α. The ED50 value for 13,14-dihydro PGF2α as a luteolytic agent in hamsters is 1.5 μg/100 g.