82864-43-5
Chemical Structure
8(9)-EET
- CAS No.: 82864-43-5
- Formula:C20H32O3
- Molecular Weight:320.47
InChIKey: DBWQSCSXHFNTMO-QJVNBQAESA-N
SMILES: CCCCC/C=C\C/C=C\C[C@H]1[C@H](O1)C/C=C\CCCC(O)=O
Biological Activity: 8(9)-EET is one of the main metabolites produced by the metabolism of arachidonic acid (HY-109590) through the cytochrome P450 epoxide pathway. 8(9)-EET is an effective substrate for COX-1 and COX-2. 8(9)-EET activates PPARα in HEK293 cells and inhibits the activity of NF-κB induced by IL-1β in a PPARα-dependent and -independent manner. The (8S,9R)-isomer of 8(9)-EET ([(8S,9R)-EET]) causes vasoconstriction, thereby reducing renal plasma flow and glomerular filtration rate[1][2][3][4][5].
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8(9)-EET | 8(9)-EET is one of the main metabolites produced by the metabolism of arachidonic acid (HY-109590) through the cytochrome P450 epoxide pathway. 8(9)-EET is an effective substrate for COX-1 and COX-2. 8(9)-EET activates PPARα in HEK293 cells and inhibits the activity of NF-κB induced by IL-1β in a PPARα-dependent and -independent manner. The (8S,9R)-isomer of 8(9)-EET ([(8S,9R)-EET]) causes vasoconstriction, thereby reducing renal plasma flow and glomerular filtration rate. | |||||||||||||||||||||
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References
- [1]. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982). [Content Brief]
- [2]. Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem. Biophys. Res. Commun. 183(1), 138-143 (1992). [Content Brief]
- [3]. Bystrom, J., Wray, J.A., Sugden, M.C., et al. Endogenous epoxygenases are modulators of monocyte/macrophage activity. PloS One 6(10), e26591 (2011). [Content Brief]
- [4]. Rand, A.A., Barnych, B., Morisseau, C., et al. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc. Natl. Acad. Sci. USA 114(17), 4370-4375 (2017). [Content Brief]
- [5]. Katoh T, et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 1991 Oct;261(4 Pt 2):F578-86. [Content Brief]
