8(S)-HETE

8(S)-HETE is a major lipoxygenase product in PMA-treated murine epidermis. It activates mouse keratinocyte protein kinase C with an IC50 of 100 μM. 8(S)-HETE also activates PPARα selectively at concentrations as low as 0.3 μM. Stereochemical assignment of the (S) enantiomer is based on comparison of chiral HPLC retention times to published results.

8(S)-HETrE is a monohydroxy polyunsaturated fatty acid produced by rabbit neutrophil lipoxygenase when dihomo-γ-linolenic acid is used as a substrate. Although the biological activities of 8(S)-HETrE have not been well characterized, it is expected to behave similarly to 8(S)-HETE .

Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites.17-HETE is a cytochrome P450 (CYP450) metabolite of arachidonic acid that has stereospecific effects on sodium transport in the kidney.17(S)-HETE inhibits proximal tubule ATPase activity by as much as 70% at a concentration of 2 μM.

1-Stearoyl-2-15(S)-HETE-sn-glycero-3-PC is a phospholipid that contains stearic acid at the sn-1 position and 15(S)-HETE at the sn-2 position. It is produced via oxidation of 1-stearoyl-2-arachidonoyl-sn-glycero-3-PC by 15-lipoxygenase (15-LO).

15(S)-HETE methyl ester is a synthetic derivative of 15(S)-HETE , a major arachidonic acid metabolite from the 15-lipoxygenase pathway. Methyl esters of lipids are commonly used in formulations of nutritional supplements.

19-HETE is one of the major cytochrome P450 (CYP450) metabolites of arachidonic acid that is released from the kidney in response to angiotensin II. When formed by the CYP2E1 isoform, 19-HETE is composed of 70% and 30% of the (S) and (R) stereoisomers, respectively. Both 19(S)- and 19(R)-HETE are potent vasodilators of renal preglomerular vessels. 19(S)-HETE stimulates both renal sodium-potassium ATPase and volume absorption in the rabbit proximal straight tubule.

8(S)-HEPE is a monohydroxy fatty acid produced by lipoxygenase oxidation of EPA. It acts to promote hatching of barnacle eggs at 10 nM, although it is not clearly identified as the natural egg hatching factor.

5(S)-HETE, an endogenous metabolite found in the blood, is utilized in researching Rheumatoid Arthritis, Rhinitis, and Asthma [1] [2].

12(S)-HETE is a product of arachidonic acid metabolism through the 12-lipoxygenase pathway. It is primarily found in platelets, leukocytes, and to a lesser extent in smooth muscle cells. It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix. tetranor-12(S)-HETE is the major β-oxidation product resulting from peroxisomal metabolism of 12(S)-HETE in numerous tissues, and Lewis lung carcinoma cells. No biological function has yet been determined for tetranor-12(S)-HETE. Some data indicate it may play a role in controlling the inflammatory response in injured corneas. In some diseases (e.g., Zellweger's Syndrome) peroxisomal abnormalities result in the inability of cells to metabolize 12(S)-HETE, which may be responsible for symptoms of the disease. The tetranor derivative of 12(S)-HETE is available as a research tool for the elucidation of the metabolic fate of its parent compound.

8(R)-HETE is biosynthesized by lipoxygenation of arachidonic acid in marine invertebrates such as gorgonian corals and starfish. Stereochemical assignment of the (R) enantiomer is based on comparison of chiral HPLC retention times to published results.

Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. 16-HETE is a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation that demonstrates stereospecific biological activity. 16(S)-HETE inhibits proximal tubule ATPase activity by as much as 60% at a concentration of 2 μM.

8(S),15(S)-DiHETE is formed when 15(S)-HETE is subjected to further oxidation by 15-LO. It causes eosinophil chemotaxis with an ED50 value of 1.5 μM but is not chemotactic for neutrophils. 8(S),15(S)-DiHETE antagonizes the hyperalgesic activity of 8(R),15(S)-DiHETE and LTB4 in the rat hind paw pain model.

11(S)-HETE, an (S) enantiomer of 11(R)-HETE and a type of oxylipin, is non-enzymatically synthesized from arachidonic acid. Compared to its counterpart, 11(S)-HETE levels are found to be elevated in both isolated human plasma and serum, as well as in LPS-stimulated isolated human plasma. Notably, patients with allergic rhinitis exhibit a decrease in 11(S)-HETE levels in their serum following one year of double-mite subcutaneous immunotherapy (DM-SCIT), correlating with an enhanced quality of life, particularly in aspects related to rhinoconjunctivitis.

Novel oxylipins, referred to as docosanoids, have been derived from C22polyunsaturated fatty acids 7(S),17(S)-dihydroxy-8(E),10(Z),13(Z),15(E),19(Z)-Docosapentaenoic acid (7(S),17(S)-hydroxy DPA) is a DPA-derived analog of the 17(S)-dihydroxy series of docosanoids known as protectins. Protectin D1, a DHA-derived dihydroxy fatty acid, exhibits potent anti-inflammatory activities.1,2,3Potentially, 7(S),17(S)-hydroxy DPA demonstrates similar properties; however, its biological activity has yet to be determined. 1.Serhan, C.N., Gotlinger, K., Hong, S., et al.Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: Assignments of dihydroxy-containing docosatrienesJ. Immunol.176(3)1848-1859(2006) 2.Ariel, A., and Serhan, C.N.Resolvins and protectins in the termination program of acute inflammationTRENDS in Immunology28(4)176-183(2007) 3.Schwab, J.M., Chiang, N., Arita, M., et al.Resolvin E1 and protectin D1 activate inflammation-resolution programmesNature447(7146)869-874(2007)

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylnon-8-enoic acid is a useful organic compound for research related to life sciences. The catalog number is T66542 and the CAS number is 1311933-83-1.

9(S)-HETE is an enantiomer which makes up 50% of (±)9-HETE . There are no reports of 9(S)-HETE occurring as an enzymatic lipoxygenation product. Whereas 12(S)-HETE promotes adhesion of several cell lines to endothelial cell monolayes, 9(S)-HETE and other positional HETEs are without effect. Stereochemical assignment of the (S) enantiomer is based on comparison of chiral HPLC retention times to published results.

1-Stearoyl-2-15(S)-HETE-sn-glycero-3-PE is a phospholipid that contains stearic acid at the sn-1 position and 15(S)-HETE at the sn-2 position. It is formed in human peripheral monocytes activated by the calcium ionophore A23187 by direct oxidation of 1-stearoyl-2-arachidonoyl-sn-glycero-3-PE by 15-LO. Phosphoethanolamine (PE) HETEs (PE-HETEs), including 1-stearoyl-2-15(S)-HETE-sn-glycero-3-PE, are the main source of esterified HETE in ionophore-activated monocytes.

5(S)-HETE lactone is a cyclic ester formed by acid-catalyzed nucleophilic addition of the C-5 hydroxyl to the C-1 carboxyl of 5(S)-HETE. The ability of (±)5-HETE lactone to inhibit rat basophilic leukemia cell 5-lipoxygenase (IC50 = 27 μM) may be entirely due to the 5(S) isomer, but the enantiomers have not been tested separately.

G(8-O-4)S Glycerol is a natural product for research related to life sciences. The catalog number is TN5408 and the CAS number is 1313434-74-0.

S(-)-8-Hydroxy-DPAT hydrobromide is an agonist of 5-HT1A serotonin receptor.

Isoprostanes are produced by the non-enzymatic, free radical peroxidation of phospholipid-esterified arachidonic acid. They have been used as biomarkers of oxidative stress, but they also have been found to have potent biological activity. ent-8-iso-15(S)-Prostaglandin F2α (ent-8-iso-15(S)-PGF2α) is a potent vasoconstrictor of porcine retinal and brain microvessels with EC50 values of 15 and 24 nM, respectively. This isoprostane is about ten-fold more potent than 8-iso-PGF2α in a whole blood platelet aggregation inhibition assay.

8(R),11(S)-DiHODE, a fungal oxylipin identified in various Aspergillus species, is synthesized through the isomerization of an 8(R)-HpODE intermediate during linoleic acid oxidation.

(1'R,3a'R,8a'S,9'S,9a'S)-1'-Methyl-3'-oxo-N,N-diphenyl-3',3a',5',7',8',8a',9',9a'-octahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carboxamide is a useful organic compound for research related to life sciences. The catalog number is T67324 and the CAS number is 900160-98-7.

12(S)-HETE is the predominant lipoxygenase product of mammalian platelets. [1] It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix at 0.1μM181M.[2][3]

CAY10514 is an aromatic analog of 8(S)-HETE. It acts as a dual agonist of PPARα and PPARγ with EC50 values of 0.173 and 0.642 μM, respectively.