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Chemical Compound Review:

CHEMBL245466 (5E,8E,11E)-13-(3- pentyloxiran-2...

Synonyms: LS-157165, AC1NS3ZT, 14(15)-EpETrE, (+/-)14,15-EET, 81276-03-1, ...

Wu, S. et al., Peri, K.G. et al., Gross, G.J. et al., Chen, J.K. et al., Peri, K.G. et al., et al.

Gauthier, Edwards, Falck, Reddy, Campbell, Gross, Falck, Gross, Isbell, Moore, Nithipatikom, Fang, Faraci, Kaduce, Harmon, Modrick, Hu, Moore, Falck, Weintraub, Spector,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of 14,15-epoxyeicosatrienoic acid

Importantly, neither 14,15-epoxyeicosatrienoic acid nor 19-hydroxyeicosatetraenoic acid significantly improved functional recovery following global ischemia, demonstrating the specificity of the biological effect for the 11, 12-epoxyeicosatrienoic acid regioisomer [1].

High impact information on 14,15-epoxyeicosatrienoic acid

In addition to its important functions in detoxification of foreign chemicals and biosynthesis of steroid hormones, the cytochrome P450 enzyme system metabolizes arachidonate to 14,15-epoxyeicosatrienoic acid (14,15-EET) [2].
Moreover, 5,6-epoxyeicosatrienoic acid and 14,15-epoxyeicosatrienoic acid, the cytochrome P450-dependent metabolites of AA, significantly stimulated MAPK activity in renal proximal tubule epithelial cells [3].
Fibroblast growth factor-2 is a downstream mediator of phosphatidylinositol 3-kinase-Akt signaling in 14,15-epoxyeicosatrienoic acid-induced angiogenesis [4].
14,15-Epoxyeicosatrienoic acid potentiated the effect of arginine vasopressin to enhance [3H]thymidine incorporation [5].
Permeability increased in both groups after the Ca2+ ionophore A23187 or 14,15-epoxyeicosatrienoic acid, independent of store depletion [6].

Biological context of 14,15-epoxyeicosatrienoic acid

14,15-Epoxyeicosatrienoic acid inhibits platelet aggregation in mouse cerebral arterioles [7].
This is the first direct evidence of stimulation of an immediate-early gene product, specifically PGHS-2, by an AA epoxygenase metabolite, 14,15-epoxyeicosatrienoic acid, as well as of a heterologous regulation of PGHS-2 synthesis by these monoxygenase products [8].
Effect of 14,15-epoxyeicosatrienoic acid infusion on blood pressure in normal and hypertensive rats [9].

Anatomical context of 14,15-epoxyeicosatrienoic acid

14,15-Epoxyeicosatrienoic acid metabolism in endothelial cells [10].
However, we find that like 14,15-epoxyeicosatrienoic acid (14,15-EET), 20-HETE produces dilation of mouse basilar artery preconstricted with U-46619 in vitro [11].
14,15-epoxyeicosatrienoic acid represents a transferable endothelium-dependent relaxing factor in bovine coronary arteries [12].
We demonstrate that canine pulmonary microsomes metabolize [1-(14)C]AA to a variety of products, including the cytochrome P-450 metabolites 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid (EET) [13].

Gene context of 14,15-epoxyeicosatrienoic acid

RP-HPLC-MS analysis revealed that CYP2C19 oxygenated arachidonic acid to 19-HETE, 14,15-epoxyeicosatrienoic acid (EET), and 8,9-EET as main metabolites [14].
This blockade by CYP450 inhibitors could be overcome by the addition of the AA epoxygenase metabolite 14,15-epoxyeicosatrienoic acid (14,15-EET); other EET regio-isomers were unable to elevate PGHS-2 mRNA level [15].
Preincubation of somatotrophs with somatostatin inhibited growth hormone-releasing hormone-stimulated growth hormone secretion, cAMP accumulation, and 14,15-epoxyeicosatrienoic acid stimulated cAMP accumulation [16].
Mechanism of rat mesenteric arterial KATP channel activation by 14,15-epoxyeicosatrienoic acid [17].
Four isomers of epoxyeicosatrienoic acid (EET) can be formed by cytochrome P-450 oxidation of arachidonic acid: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid [18].

Analytical, diagnostic and therapeutic context of 14,15-epoxyeicosatrienoic acid

On the other hand, a group of regioisomers resulting from the epoxidation of AA, including 5,6-, 8,9-, 11,12- and 14,15-epoxyeicosatrienoic acid (EETs), have been shown to reduce ischemic and/or reperfusion injury in the heart and vasculature [19].
Determination of 14,15-epoxyeicosatrienoic acid and 14,15-dihydroxyeicosatrienoic acid by fluoroimmunoassay [20].
It is sensitive to stimulants and inhibitors of the cytochrome-P450-dependent epoxygenase system and co-migrates on HPLC with 14,15-epoxyeicosatrienoic acid (14,15-EET), which is an epoxygenase product [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]
Heparin-binding EGF-like growth factor mediates the biological effects of P450 arachidonate epoxygenase metabolites in epithelial cells. Chen, J.K., Capdevila, J., Harris, R.C. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
Phospholipase A2-mediated activation of mitogen-activated protein kinase by angiotensin II. Dulin, N.O., Alexander, L.D., Harwalkar, S., Falck, J.R., Douglas, J.G. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
Fibroblast growth factor-2 is a downstream mediator of phosphatidylinositol 3-kinase-Akt signaling in 14,15-epoxyeicosatrienoic acid-induced angiogenesis. Zhang, B., Cao, H., Rao, G.N. J. Biol. Chem. (2006) [Pubmed]
Endogenous non-cyclooxygenase metabolites of arachidonic acid modulate growth and mRNA levels of immediate-early response genes in rat mesangial cells. Sellmayer, A., Uedelhoven, W.M., Weber, P.C., Bonventre, J.V. J. Biol. Chem. (1991) [Pubmed]
Resistance to store depletion-induced endothelial injury in rat lung after chronic heart failure. Alvarez, D.F., King, J.A., Townsley, M.I. Am. J. Respir. Crit. Care Med. (2005) [Pubmed]
14,15-Epoxyeicosatrienoic acid inhibits platelet aggregation in mouse cerebral arterioles. Heizer, M.L., McKinney, J.S., Ellis, E.F. Stroke (1991) [Pubmed]
Stimulation of prostaglandin G/H synthase-2 expression by arachidonic acid monoxygenase product, 14,15-epoxyeicosatrienoic acid. Peri, K.G., Varma, D.R., Chemtob, S. FEBS Lett. (1997) [Pubmed]
Effect of 14,15-epoxyeicosatrienoic acid infusion on blood pressure in normal and hypertensive rats. Lin, W.K., Falck, J.R., Wong, P.Y. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
14,15-Epoxyeicosatrienoic acid metabolism in endothelial cells. VanRollins, M., Kaduce, T.L., Knapp, H.R., Spector, A.A. J. Lipid Res. (1993) [Pubmed]
20-Hydroxyeicosatetraenoic acid is a potent dilator of mouse basilar artery: role of cyclooxygenase. Fang, X., Faraci, F.M., Kaduce, T.L., Harmon, S., Modrick, M.L., Hu, S., Moore, S.A., Falck, J.R., Weintraub, N.L., Spector, A.A. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
14,15-epoxyeicosatrienoic acid represents a transferable endothelium-dependent relaxing factor in bovine coronary arteries. Gauthier, K.M., Edwards, E.M., Falck, J.R., Reddy, D.S., Campbell, W.B. Hypertension (2005) [Pubmed]
Inhibition of cytochrome P-450 attenuates hypoxemia of acute lung injury in dogs. Stephenson, A.H., Sprague, R.S., Weintraub, N.L., McMurdo, L., Lonigro, A.J. Am. J. Physiol. (1996) [Pubmed]
Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS. Bylund, J., Ericsson, J., Oliw, E.H. Anal. Biochem. (1998) [Pubmed]
A role for protein kinase C alpha in stimulation of prostaglandin G/H synthase-2 transcription by 14,15-epoxyeicosatrienoic acid. Peri, K.G., Almazan, G., Varma, D.R., Chemtob, S. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
Effect of epoxyeicosatrienoic acids on growth hormone release from somatotrophs. Snyder, G.D., Yadagiri, P., Falck, J.R. Am. J. Physiol. (1989) [Pubmed]
Mechanism of rat mesenteric arterial KATP channel activation by 14,15-epoxyeicosatrienoic acid. Ye, D., Zhou, W., Lu, T., Jagadeesh, S.G., Falck, J.R., Lee, H.C. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
Collisionally induced dissociation of epoxyeicosatrienoic acids and epoxyeicosatrienoic acid-phospholipid molecular species. Bernstrom, K., Kayganich, K., Murphy, R.C. Anal. Biochem. (1991) [Pubmed]
Cytochrome P450 and arachidonic acid metabolites: role in myocardial ischemia/reperfusion injury revisited. Gross, G.J., Falck, J.R., Gross, E.R., Isbell, M., Moore, J., Nithipatikom, K. Cardiovasc. Res. (2005) [Pubmed]
Determination of 14,15-epoxyeicosatrienoic acid and 14,15-dihydroxyeicosatrienoic acid by fluoroimmunoassay. Nithipatikom, K., Falck, J.R., Bhatt, R.K., Hanke, C.J., Campbell, W.B. Anal. Biochem. (1997) [Pubmed]
Production of epoxygenase metabolite by human reproductive tissues. Patel, L., Sullivan, M.H., Elder, M.G. Prostaglandins (1989) [Pubmed]

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