(±)18hete

(±)18-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid. When formed by the CYP2E1 isoform, 18-HETE is comprised 100% of the (R) isomer. 18(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, whereas 18(S)-HETE does not affect perfusion pressure. 18-HETE has negligible effects on ATPase activity. 18(R)-HETE at 1 μM completely blocks 20-HETE-induced vasoconstriction of renal arterioles.

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.

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.

(±)5-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. It contains equal amounts of 5(S)-HETE and 5(R)-HETE. (±)5-HETE induces the aggregation of isolated neutrophils with an IC50 value of 200 nM.[1]

5(R)-HETE is a rare lipoxygenase product of arachidonic acid. Nearly all plant and animal 5-LOs produce 5(S)-HETE, but the presence of a 5(R)-LO and the synthesis of 5(R)-HpETE and 5(R)-HETE have been confirmed in oocytes of the bivalve mollusk, S. solidissima. 5(R)-HETE is more potent than the (S)-enantiomer as a chemotactic agent for human neutrophils.

8(S)-HETE, a major lipoxygenase product in PMA-treated murine epidermis, activates mouse keratinocyte protein kinase C with an IC50 of 100 μM and selectively activates PPARα at concentrations as low as 0.3 μM. The stereochemical assignment of the (S) 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. 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(R)-HETE is an inactive isomer of 17-HETE, whereas the (S) enantiomer can inhibit proximal tubule ATPase activity at a concentration of 2 μM.

9(R)-HETE, which constitutes 50% of (±)9-HETE, activates RXRγ-dependent transcription 1.5-fold relative to a control at a concentration of 300 nM. The stereochemical assignment of the (R) enantiomer is based on the comparison of chiral HPLC retention times to published results.

Biosynthesis of 12(R)-HETE in invertebrates is via lipoxygenation of arachidonic acid . In mammals, 12(R)-HETE can be produced by 12(R)-LOs and also by CYP450 oxidation. The activity of 12(R)-HETE in mammals is predominantly proinflammatory. 12(R)-HETE exhibits dose-dependent leukocyte chemotaxis at concentrations as low as 100 nM, and lowers intraocular pressure in rabbits.

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.

11(R)-HETE is biosynthesized by 11(R)-LOs of the sea urchin, S. purpuratus, and the fresh water hydra, H. vulgaris. The biological activity of 11(R)-HETE relates to oocyte maturation and tentacle regeneration, respectively, in these two species. 11(R)-HETE is also produced when aspirin-treated recombinant COX-2 is incubated with arachidonic acid. 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. 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.[1]

19(R)-HETE is a renal artery vasodilator that can be used to study angiotensin II-induced cardiac hypertrophy.

Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)16-HETE is the racemic version of a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation. The biological activity of 16-HETE is stereospecific. 16(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, however 16(S)-HETE does not affect perfusion pressure. At a concentration of 2 μM the (S)-enantiomer of 16-HETE inhibits proximal tubule ATPase activity by as much as 60%, whereas the (R)-isomer has negligible effects on ATPase activity.

8(R)-HETE is biosynthesized via lipoxygenation of arachidonic acid in marine invertebrates, including gorgonian corals and starfish. The stereochemical assignment of the (R) enantiomer is confirmed by comparing chiral HPLC retention times to published results.

(±)9-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. The individual R and S isomers of racemic HETEs have been separated and identified using chiral phase HPLC. The racemic HETEs have been quantified as an index of lipid peroxidation using GC/MS.

(±)11-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid . The individual R and S isomers of racemic HETEs have been separated and identified using chiral phase HPLC. The racemic HETEs have been quantified as an index of lipid peroxidation using GC/MS.

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.