Inhibition of soluble epoxide hydrolase by trans-4- [4-(3-adamantan-1-yl- ureido)-cyclohexyloxy]-benzoic acid is protective against ischemia-repefusion injury

Journal of Cardiovascular Pharmacology

Volumn 55, Issue 1, 2010, Pages 67-73

  Chaudhary, Ketul R ^a   Abukhashim, Mohamed ^a   Hwang, Sung Hee ^b   Hammock, Bruce D ^b   Seubert, John M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cardioprotection; Epoxyeicosatrienoic acid; Ischemia and reperfusion; SEH inhibitors

Indexed keywords

14,15 EPOXY 5,8,11 ICOSATRIENOIC ACID; 2 MORPHOLINO 8 PHENYLCHROMONE; 4 [4 (3 ADAMANTAN 1 YL UREIDO)CYCLOHEXYLOXY]BENZOIC ACID; EPOXIDE HYDROLASE; PHOSPHATIDYLINOSITOL 3 KINASE INHIBITOR; TRIPHENYLTETRAZOLIUM; UNCLASSIFIED DRUG; WORTMANNIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG METABOLISM; FEMALE; HEART INFARCTION SIZE; HEART MUSCLE ISCHEMIA; HEART PROTECTION; HEART VENTRICLE PRESSURE; INHALATIONAL DRUG ADMINISTRATION; MALE; MOUSE; NONHUMAN; PHENOTYPE; PRIORITY JOURNAL; REPERFUSION; REPERFUSION INJURY;

EID: 75749084460     PISSN: 01602446     EISSN: None     Source Type: Journal    
DOI: 10.1097/FJC.0b013e3181c37d69     Document Type: Article

References (31)

1. Seubert JM, Sinal CJ, Graves J, et al. Role of soluble epoxide hydrolase in postischemic recovery of heart contractile function. Circ Res. 2006;99: 442-450.
2. Seubert JM, Zeldin DC, Nithipatikom K, et al. Role of epoxyeicosatrienoic acids in protecting the myocardium following ischemia/ reperfusion injury. Prostaglandins Other Lipid Mediat. 2007;82:50-59.
3. Spector AA, Norris AW. Action of epoxyeicosatrienoic acids on cellular function. Am J Physiol Cell Physiol. 2007;292:C996-C1012.
4. Spector AA, Fang X, Snyder GD, et al. Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Prog Lipid Res. 2004;43:55-90.
5. Chiamvimonvat N, Ho CM, Tsai HJ, et al. The soluble epoxide hydrolase as a pharmaceutical target for hypertension. J Cardiovasc Pharmacol. 2007;50:225-237.
6. Gauthier KM, YangW, Gross GJ, et al. Roles of epoxyeicosatrienoic acids in vascular regulation and cardiac preconditioning. J Cardiovasc Pharmacol. 2007;50:601-608.
7. Hao CM, Breyer MD. Physiologic and pathophysiologic roles of lipid mediators in the kidney. Kidney Int. 2007;71:1105-1115.
8. Pratt PF, Medhora M, Harder DR. Mechanisms regulating cerebral blood flow as therapeutic targets. Curr Opin Investig Drugs. 2004;5: 952-956.
9. Batchu SN, Law E, Brocks DR, et al. Epoxyeicosatrienoic acid prevents postischemic electrocardiogram abnormalities in an isolated heart model. J Mol Cell Cardiol. 2009;46:67-74.
10. Chaudhary KR, Batchu SN, Das D, et al. Role of B-type natriuretic peptide in epoxyeicosatrienoic acid mediated improved postischemic recovery of heart contractile function. Cardiovasc Res. 2009;83:362-370.
11. Gross GJ, Gauthier KM, Moore J, et al. Effects of the selective EET antagonist, 14,15-EEZE, on cardioprotection produced by exogenous or endogenous EETs in the canine heart. Am J Physiol Heart Circ Physiol. 2008;294:H2838-H2844.
12. Katragadda D, Batchu SN, Cho WJ, et al. Epoxyeicosatrienoic acids limit damage to mitochondrial function following stress in cardiac cells. J Mol Cell Cardiol. 2009;46:867-875.
13. Seubert J, Yang B, Bradbury JA, et al. Enhanced postischemic functional recovery in CYP2J2 transgenic hearts involves mitochondrial ATPsensitive K+ channels and p42/p44 MAPK pathway. Circ Res. 2004;95: 506-514.
14. Wang YX, Zeng XJ, Lu LQ, et al. [Effects of 11, 12-epoxyeicosatrienoic acid preconditioning and postconditioning on Ca(2+)- handling proteins in myocardial ischemia/reperfusion injury in rats]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2007;29:787-791.
15. Motoki A, Merkel MJ, Packwood WH, et al. Soluble epoxide hydrolase inhibition and gene deletion are protective against myocardial ischemiareperfusion injury in vivo. Am J Physiol Heart Circ Physiol. 2008;295: H2128-H2134.
16. Morisseau C, Hammock BD. Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu Rev Pharmacol Toxicol. 2005;45: 311-333.
17. Zhang W, Koerner IP, Noppens R, et al. Soluble epoxide hydrolase: a novel therapeutic target in stroke. J Cereb Blood Flow Metab. 2007;27: 1931-1940.
18. Harris TR, Li N, Chiamvimonvat N, et al. The potential of soluble epoxide hydrolase inhibition in the treatment of cardiac hypertrophy. Congest Heart Fail. 2008;14:219-224.
19. Monti J, Fischer J, Paskas S, et al. Soluble epoxide hydrolase is a susceptibility factor for heart failure in a rat model of human disease. Nat Genet. 2008;40:529-537.
20. Ai D, Pang W, Li N, et al. Soluble epoxide hydrolase plays an essential role in angiotensin II-induced cardiac hypertrophy. Proc Natl Acad Sci U S A. 2009;106:564-569.
21. Li J, Carroll MA, Chander PN, et al. Soluble epoxide hydrolase inhibitor, AUDA, prevents early salt-sensitive hypertension. Front Biosci. 2008;13: 3480-3487.
22. Morisseau C, Du G, Newman JW, et al. Mechanism of mammalian soluble epoxide hydrolase inhibition by chalcone oxide derivatives. Arch Biochem Biophys. 1998;356:214-228.
23. Morisseau C, Goodrow MH, Dowdy D, et al. Potent urea and carbamate inhibitors of soluble epoxide hydrolases. Proc Natl Acad Sci U S A. 1999; 96:8849-8854.
24. Liu JY, Tsai HJ, Hwang SH, et al. Pharmacokinetic optimization of four soluble epoxide hydrolase inhibitors for use in a murine model of inflammation. Br J Pharmacol. 2009;156:284-296.
25. Kim IH, Morisseau C,Watanabe T, et al. Design, synthesis, and biological activity of 1,3-disubstituted ureas as potent inhibitors of the soluble epoxide hydrolase of increased water solubility. J Med Chem. 2004;47: 2110-2122.
26. Hwang SH, Tsai HJ, Liu JY, et al. Orally bioavailable potent soluble epoxide hydrolase inhibitors. J Med Chem. 2007;50:3825-3840.
27. Revermann M, Barbosa-Sicard E, Dony E, et al. Inhibition of the soluble epoxide hydrolase attenuates monocrotaline-induced pulmonary hypertension in rats. J Hypertens. 2009;27:322-331.
28. Xu D, Li N, He Y, et al. Prevention and reversal of cardiac hypertrophy by soluble epoxide hydrolase inhibitors. Proc Natl Acad Sci U S A. 2006;103: 18733-18738.
29. Anandan SK, Do ZN, Webb HK, et al. Non-urea functionality as the primary pharmacophore in soluble epoxide hydrolase inhibitors. Bioorg Med Chem Lett. 2009;19:1066-1070.
30. Xie Y, Liu Y, Gong G, et al. Discovery of potent non-urea inhibitors of soluble epoxide hydrolase. Bioorg Med Chem Lett. 2009;19:2354-2359.
31. Dhanasekaran A, Gruenloh SK, Buonaccorsi JN, et al. Multiple antiapoptotic targets of the PI3K/Akt survival pathway are activated by epoxyeicosatrienoic acids to protect cardiomyocytes from hypoxia/anoxia. Am J Physiol Heart Circ Physiol. 2008;294:H724-H735.