(±)8(9)-EET-d11 Chemical Properties

solubility 

DMF: 50 mg/ml
DMSO: 50 mg/ml
Ethanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml

(±)8(9)-EET-d11 Usage And Synthesis

Description

(±)8(9)-EET-d11 is intended for use as an internal standard for the quantification of (±)8(9)-EET (Item No. 50351) by GC- or LC-MS. (±)8(9)-EET is a racemic mixture of the R/S enantiomeric forms biosynthesized from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 (±)8(9)-EET is a major cytochrome P450 (CYP) metabolite in the renal cortex.3 It activates PPARα in HEK293 cells when used at a concentration of 1 µM but inhibits NF-κB activity induced by IL-1β in a PPARα-dependent and -independent fashion.4 It is also a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 µM.5 (8S,9R)-EET (1 µg/kg), but not (8R,9S)-EET, reduces the glomerular filtration rate (GFR) through COX-dependent pre-glomerular vasoconstriction in rats.6WARNING This product is not for human or veterinary use.

References

[1] N. CHACOS . Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid[J]. Biochemical and biophysical research communications, 1982, 104 3: Pages 916-922. DOI: 10.1016/0006-291x(82)91336-5
[2] E. OLIW J O F Guengerich. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates.[J]. The Journal of Biological Chemistry, 1982, 109 1: 3771-3781. DOI: 10.1016/s0021-9258(18)34848-8
[3] JI Y. ZHANG . Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase[J]. Biochemical and biophysical research communications, 1992, 183 1: Pages 138-143. DOI: 10.1016/0006-291x(92)91619-2
[4] JONAS BYSTROM. Endogenous epoxygenases are modulators of monocyte/macrophage activity.[J]. PLoS ONE, 2011: e26591. DOI: 10.1371/journal.pone.0026591
[5] AMY A RAND. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2017, 114 17: 4370-4375. DOI: 10.1073/pnas.1616893114
[6] T KATOH. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney.[J]. American Journal of Physiology, 1991, 261 4 Pt 2: F578-86. DOI: 10.1152/ajprenal.1991.261.4.f578