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Chemical Compound Review:

E5641_SIGMA (5E,8E)-10-[3-[(E)-oct-2- enyl]oxiran-2...

Synonyms: HMDB04673, LS-59241, AC1NS3ZE, 11,12-Eet, 81276-02-0, ...

Wu, S. et al., Wei, Y. et al., Fisslthaler, B. et al., Yang, Q. et al., Imig, J.D. et al., et al.

Sacerdoti, Colombrita, Di Pascoli, Schwartzman, Bolognesi, Falck, Gatta, Abraham, Imig, Inscho, Deichmann, Reddy, Falck, Sacerdoti, Bolognesi, Di Pascoli, Gatta, McGiff, Schwartzman, Abraham, Imig, Zhao, Falck, Wei, Capdevila, Falck, Reddy, Reddy, Bondlela, Krishna, Ji, Sun, Liao, Seki, Wang, Miyata, Laniado-Schwartzman,

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Disease relevance of 11,12-epoxyeicosatrienoic acid

Based on these data, we conclude that (a) CYP2J3 is one of the predominant enzymes responsible for the oxidation of endogenous arachidonic acid pools in rat heart myocytes and (b) 11,12-epoxyeicosatrienoic acid may play an important functional role in the response of the heart to ischemia [1].

High impact information on 11,12-epoxyeicosatrienoic acid

Here we show that the induction of cytochrome P450 (CYP) 2C8/34 in native porcine coronary artery endothelial cells by beta-naphthoflavone enhances the formation of 11,12-epoxyeicosatrienoic acid, as well as EDHF-mediated hyperpolarization and relaxation [2].
11,12-Epoxyeicosatrienoic acid stimulates endogenous mono-ADP-ribosylation in bovine coronary arterial smooth muscle [3].
11,12-Epoxyeicosatrienoic acid-induced inhibition of FOXO factors promotes endothelial proliferation by down-regulating p27Kip1 [4].
Nifedipine enhanced endothelial CYP2C protein expression, as well as the generation of 11,12-epoxyeicosatrienoic acid [5].
The current study determined the contribution of protein kinase-A (PKA) and protein kinase-G (PKG) to the vasodilation elicited by the N-methylsulfonimide analog of 11,12-epoxyeicosatrienoic acid (11, 12-EET) [6].

Biological context of 11,12-epoxyeicosatrienoic acid

OBJECTIVES: Epoxygenase metabolites produced by the kidney affect renal blood flow and tubular transport function and 11,12-epoxyeicosatrienoic acid (11,12-EET) has been putatively identified as an endothelium-derived hyperpolarizing factor [7].
The IC50 value for production of 11,12-epoxy-5,8,14-eicosatrienoic acid (11,12-EET) by CYP4A2 and 4A3 averaged 12.7 nM and 22.0 nM, respectively [8].

Anatomical context of 11,12-epoxyeicosatrienoic acid

Functional implications of a newly characterized pathway of 11,12-epoxyeicosatrienoic acid metabolism in arterial smooth muscle [9].
Arachidonate metabolites of cortical microsomes were identified by g.c.-m.s. as 20- and 19-hydroxyeicosatetraenoic acid, 11,12-epoxyeicosatrienoic acid and 11,12-dihydroxyeicosatrienoic acid [10].
11,12-Epoxyeicosatrienoic acid (11,12-EET), a potent vasodilator produced by the endothelium, acts on calcium-activated potassium channels and shares biological activities with the heme oxygenase/carbon monoxide (HO/CO) system [11].
Potentiation of Ca2+ signaling in endothelial cells by 11,12-epoxyeicosatrienoic acid [12].

Associations of 11,12-epoxyeicosatrienoic acid with other chemical compounds

A concentration of synthetic 14,15- and 11,12-epoxyeicosatrienoic acid of 5 micrograms/ml CSF had little or no effect on diameter, whereas 8,9-epoxyeicosatrienoic acid caused a maximum dilation of 8% [13].
Because 11,12-epoxyeicosatrienoic acid (11,12-EET) inhibits ENaC activity in the CCD (Wei Y, Lin DH, Kemp R, Yaddanapudi GSS, Nasjletti A, Falck JR, and Wang WH. J Gen Physiol 124: 719-727, 2004), we examined the role of 11,12-EET in mediating the effect of adenosine on ENaC [14].

Gene context of 11,12-epoxyeicosatrienoic acid

11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression [15].
11,12-Epoxyeicosatrienoic acid stimulates heme-oxygenase-1 in endothelial cells [16].
Activation of rat mesenteric arterial KATP channels by 11,12-epoxyeicosatrienoic acid [17].

Analytical, diagnostic and therapeutic context of 11,12-epoxyeicosatrienoic acid

Close arterial injection of 1 to 20 micrograms of 5,6-, 8,9- and 11,12-epoxyeicosatrienoic acid (EET) dose-dependently decreased perfusion pressure [18].
Effect of 11,12-epoxyeicosatrienoic acid as an additive to St. Thomas' cardioplegia and University of Wisconsin solutions on endothelium-derived hyperpolarizing factor-mediated function in coronary microarteries: influence of temperature and time [19].
Using microelectrode potential measurements, we tested the involvement of Cl- conductances in the hyperpolarization induced by 5,6- and 11,12-epoxyeicosatrienoic acid (EET) in airway smooth muscle (ASM) cells [20].
CYP epoxygenase activity was analyzed by reverse-phase high-pressure liquid chromatography; and the results showed that 11,12- epoxyeicosatrienoic acid (EET) was the major product metabolized by CYP epoxygenases in rat corpora cavernosa [21].

References

Molecular cloning, expression, and functional significance of a cytochrome P450 highly expressed in rat heart myocytes. Wu, S., Chen, W., Murphy, E., Gabel, S., Tomer, K.B., Foley, J., Steenbergen, C., Falck, J.R., Moomaw, C.R., Zeldin, D.C. J. Biol. Chem. (1997) [Pubmed]
Cytochrome P450 2C is an EDHF synthase in coronary arteries. Fisslthaler, B., Popp, R., Kiss, L., Potente, M., Harder, D.R., Fleming, I., Busse, R. Nature (1999) [Pubmed]
11,12-Epoxyeicosatrienoic acid stimulates endogenous mono-ADP-ribosylation in bovine coronary arterial smooth muscle. Li, P.L., Chen, C.L., Bortell, R., Campbell, W.B. Circ. Res. (1999) [Pubmed]
11,12-Epoxyeicosatrienoic acid-induced inhibition of FOXO factors promotes endothelial proliferation by down-regulating p27Kip1. Potente, M., Fisslthaler, B., Busse, R., Fleming, I. J. Biol. Chem. (2003) [Pubmed]
Nifedipine increases cytochrome P4502C expression and endothelium-derived hyperpolarizing factor-mediated responses in coronary arteries. Fisslthaler, B., Hinsch, N., Chataigneau, T., Popp, R., Kiss, L., Busse, R., Fleming, I. Hypertension (2000) [Pubmed]
Afferent arteriolar vasodilation to the sulfonimide analog of 11, 12-epoxyeicosatrienoic acid involves protein kinase A. Imig, J.D., Inscho, E.W., Deichmann, P.C., Reddy, K.M., Falck, J.R. Hypertension (1999) [Pubmed]
Enhanced renal microvascular reactivity to angiotensin II in hypertension is ameliorated by the sulfonimide analog of 11,12-epoxyeicosatrienoic acid. Imig, J.D., Zhao, X., Falck, J.R., Wei, S., Capdevila, J.H. J. Hypertens. (2001) [Pubmed]
Cytochrome P450 4A isoform inhibitory profile of N-hydroxy-N'-(4-butyl-2-methylphenyl)-formamidine (HET0016), a selective inhibitor of 20-HETE synthesis. Seki, T., Wang, M.H., Miyata, N., Laniado-Schwartzman, M. Biol. Pharm. Bull. (2005) [Pubmed]
Functional implications of a newly characterized pathway of 11,12-epoxyeicosatrienoic acid metabolism in arterial smooth muscle. Fang, X., Kaduce, T.L., Weintraub, N.L., VanRollins, M., Spector, A.A. Circ. Res. (1996) [Pubmed]
Regulation of arachidonic acid metabolism by cytochrome P-450 in rabbit kidney. Schwartzman, M.L., Abraham, N.G., Carroll, M.A., Levere, R.D., McGiff, J.C. Biochem. J. (1986) [Pubmed]
Rat mesenteric arterial dilator response to 11,12-epoxyeicosatrienoic acid is mediated by activating heme oxygenase. Sacerdoti, D., Bolognesi, M., Di Pascoli, M., Gatta, A., McGiff, J.C., Schwartzman, M.L., Abraham, N.G. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
Potentiation of Ca2+ signaling in endothelial cells by 11,12-epoxyeicosatrienoic acid. Mombouli, J.V., Holzmann, S., Kostner, G.M., Graier, W.F. J. Cardiovasc. Pharmacol. (1999) [Pubmed]
Brain synthesis and cerebrovascular action of epoxygenase metabolites of arachidonic acid. Amruthesh, S.C., Falck, J.R., Ellis, E.F. J. Neurochem. (1992) [Pubmed]
Adenosine inhibits ENaC via cytochrome P-450 epoxygenase-dependent metabolites of arachidonic acid. Wei, Y., Sun, P., Wang, Z., Yang, B., Carroll, M.A., Wang, W.H. Am. J. Physiol. Renal Physiol. (2006) [Pubmed]
11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression. Falck, J.R., Reddy, L.M., Reddy, Y.K., Bondlela, M., Krishna, U.M., Ji, Y., Sun, J., Liao, J.K. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
11,12-Epoxyeicosatrienoic acid stimulates heme-oxygenase-1 in endothelial cells. Sacerdoti, D., Colombrita, C., Di Pascoli, M., Schwartzman, M.L., Bolognesi, M., Falck, J.R., Gatta, A., Abraham, N.G. Prostaglandins Other Lipid Mediat. (2007) [Pubmed]
Activation of rat mesenteric arterial KATP channels by 11,12-epoxyeicosatrienoic acid. Ye, D., Zhou, W., Lee, H.C. Am. J. Physiol. Heart Circ. Physiol. (2005) [Pubmed]
Cyclooxygenase dependency of the renovascular actions of cytochrome P450-derived arachidonate metabolites. Carroll, M.A., Garcia, M.P., Falck, J.R., McGiff, J.C. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
Effect of 11,12-epoxyeicosatrienoic acid as an additive to St. Thomas' cardioplegia and University of Wisconsin solutions on endothelium-derived hyperpolarizing factor-mediated function in coronary microarteries: influence of temperature and time. Yang, Q., Zhang, R.Z., Yim, A.P., He, G.W. Ann. Thorac. Surg. (2003) [Pubmed]
Direct modulation of tracheal Cl--channel activity by 5,6- and 11,12-EET. Salvail, D., Dumoulin, M., Rousseau, E. Am. J. Physiol. (1998) [Pubmed]
Cytochrome P450 epoxygenases provide a novel mechanism for penile erection. Jin, L., Foss, C.E., Zhao, X., Mills, T.M., Wang, M.H., McCluskey, L.P., Yaddanapud, G.S., Falck, J.R., Imig, J.D., Webb, R.C. FASEB J. (2006) [Pubmed]

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