Cardioprotective effect of a dual acting epoxyeicosatrienoic acid analogue towards ischaemia reperfusion injury

British Journal of Pharmacology

Volumn 162, Issue 4, 2011, Pages 897-907

  Batchu, S N ^a   Lee, S B ^a   Qadhi, R S ^a   Chaudhary, K R ^a   El Sikhry, H ^a   Kodela, R ^b   Falck, J R ^b   Seubert, J M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF TEXAS AT DALLAS   (United States)

Author keywords

cardioprotection; EET surrogates; ischaemia reperfusion; mitochondria and sEHi

Indexed keywords

11,12 EPOXY 5,8,14 ICOSATRIENOIC ACID; 13 (2 [BUTYLAMINO] 2 OXOACETAMIDO)TRIDEC 8 ENOIC ACID; 13 (3 PROPYLUREIDO)TRIDEC 8 ENOIC ACID; 2 (4 HYDROXYPHENYL) 4 MORPHOLINOPYRIDO[3',2':4,5]FURO[3,2 D]PYRIMIDINE; CARDIOVASCULAR AGENT; EPOXIDE HYDROLASE; PHOSPHATIDYLINOSITOL 3 KINASE; RECEPTOR BLOCKING AGENT; UA 7; UA 8; UNCLASSIFIED DRUG; WORTMANNIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANOXIA; ARTICLE; C57BL 6 MOUSE; CELL DEATH; CELL STRAIN; CONTROLLED STUDY; DISORDERS OF MITOCHONDRIAL FUNCTIONS; DRUG MECHANISM; FEMALE; HEART INFARCTION; HEART LEFT VENTRICLE PRESSURE; HEART MITOCHONDRION; HEART MUSCLE ISCHEMIA; HEART MUSCLE OXYGEN CONSUMPTION; HEART MUSCLE REPERFUSION; HEART PROTECTION; ISOLATED HEART; MALE; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; NONHUMAN; PRIORITY JOURNAL; REOXYGENATION; REPERFUSION INJURY; SIGNAL TRANSDUCTION;

8,11,14-EICOSATRIENOIC ACID; ACETAMIDES; ANIMALS; APOPTOSIS; CARDIOTONIC AGENTS; CELL HYPOXIA; CELL LINE; ENZYME INHIBITORS; FEMALE; HEART; MALE; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE; MICE, INBRED C57BL; MYOCARDIAL INFARCTION; MYOCARDIAL ISCHEMIA; MYOCARDIAL REPERFUSION INJURY; MYOCYTES, CARDIAC; OLEIC ACIDS; PHOSPHATIDYLINOSITOL 3-KINASES; RATS; RECEPTORS, EICOSANOID;

EID: 79251476881     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2010.01093.x     Document Type: Article

References (38)

1. Anandan SK, Do ZN, Webb HK, Patel DV, Gless RD, (2009). Non-urea functionality as the primary pharmacophore in soluble epoxide hydrolase inhibitors. Bioorg Med Chem Lett 19: 1066-1070.
2. Batchu SN, Law E, Brocks DR, Falck JR, Seubert JM, (2009). Epoxyeicosatrienoic acid prevents postischemic electrocardiogram abnormalities in an isolated heart model. J Mol Cell Cardiol 46: 67-74.
3. Chan DC, (2006). Mitochondria: dynamic organelles in disease, aging, and development. Cell 125: 1241-1252.
4. Chaudhary KR, Abukhashim M, Hwang SH, Hammock BD, Seubert JM, (2009a). Inhibition of soluble epoxide hydrolase by trans-4-[4-(3-adamantan-1-yl-ureido)- cyclohexyloxy]-benzoic acid (t-AUCB) is protective against ischemia reperfusion injury. J Cardiovasc Pharmacol 55: 67-73.
5. Chaudhary KR, Batchu SN, Das D, Suresh MR, Falck JR, Graves JP, et al. (2009b). Role of B-type natriuretic peptide in epoxyeicosatrienoic acid-mediated improved post-ischaemic recovery of heart contractile function. Cardiovasc Res 83: 362-370.
6. Chiamvimonvat N, Ho CM, Tsai HJ, Hammock BD, (2007). The soluble epoxide hydrolase as a pharmaceutical target for hypertension. J Cardiovasc Pharmacol 50: 225-237.
7. Dhanasekaran A, Gruenloh SK, Buonaccorsi JN, Zhang R, Gross GJ, Falck JR, et al. (2008). 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 294: H724-H735.
8. Falck JR, Krishna UM, Reddy YK, Kumar PS, Reddy KM, Hittner SB, et al. (2003). Comparison of vasodilatory properties of 14,15-EET analogs: structural requirements for dilation. Am J Physiol Heart Circ Physiol 284: H337-H349.
9. Falck JR, Kodela R, Manne R, Atcha KR, Puli N, Dubasi N, et al. (2009). 14,15-epoxyeicosa-5,8,11-trienoic acid (14,15-EET) surrogates containing epoxide bioisosteres: influence upon vascular relaxation and soluble epoxide hydrolase inhibition. J Med Chem 52: 5069-5075.
10. Fang X, Kaduce TL, Weintraub NL, Spector AA, (1997). Cytochrome P450 metabolites of arachidonic acid: rapid incorporation and hydration of 14,15-epoxyeicosatrienoic acid in arterial smooth muscle cells. Prostaglandins Leukot Essent Fatty Acids 57: 367-371.
11. Fang X, Weintraub NL, Oltman CL, Stoll LL, Kaduce TL, Harmon S, et al. (2002). Human coronary endothelial cells convert 14,15-EET to a biologically active chain-shortened epoxide. Am J Physiol Heart Circ Physiol 283: H2306-H2314.
12. Fang X, Weintraub NL, McCaw RB, Hu S, Harmon SD, Rice JB, et al. (2004). Effect of soluble epoxide hydrolase inhibition on epoxyeicosatrienoic acid metabolism in human blood vessels. Am J Physiol Heart Circ Physiol 287: H2412-H2420.
13. Fitzpatrick FA, Aguirre R, Pike JE, Lincoln FH, (1980). The stability of 13,14-dihydro-15 keto-PGE2. Prostaglandins 19: 917-931.
14. Gauthier KM, Falck JR, Reddy LM, Campbell WB, (2004). 14,15-EET analogs: characterization of structural requirements for agonist and antagonist activity in bovine coronary arteries. Pharmacol Res 49: 515-524.
15. Gross GJ, Hsu A, Falck JR, Nithipatikom K, (2007). Mechanisms by which epoxyeicosatrienoic acids (EETs) elicit cardioprotection in rat hearts. J Mol Cell Cardiol 42: 687-691.
16. Jones PD, Tsai HJ, Do ZN, Morisseau C, Hammock BD, (2006). Synthesis and SAR of conformationally restricted inhibitors of soluble epoxide hydrolase. Bioorg Med Chem Lett 16: 5212-5216.
17. Juhaszova M, Zorov DB, Kim SH, Pepe S, Fu Q, Fishbein KW, et al. (2004). Glycogen synthase kinase-3beta mediates convergence of protection signaling to inhibit the mitochondrial permeability transition pore. J Clin Invest 113: 1535-1549.
18. Kaspera R, Totah RA, (2009). Epoxyeicosatrienoic acids: formation, metabolism and potential role in tissue physiology and pathophysiology. Expert Opin Drug Metab Toxicol 5: 757-771.
19. Katragadda D, Batchu SN, Cho WJ, Chaudhary KR, Falck JR, Seubert JM, (2009). Epoxyeicosatrienoic acids limit damage to mitochondrial function following stress in cardiac cells. J Mol Cell Cardiol 46: 867-875.
20. Kim IH, Morisseau C, Watanabe T, Hammock BD, (2004). 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 47: 2110-2122.
21. Lee HC, Lu T, Weintraub NL, VanRollins M, Spector AA, Shibata EF, (1999). Effects of epoxyeicosatrienoic acids on the cardiac sodium channels in isolated rat ventricular myocytes. J Physiol 519 (Pt 1): 153-168.
22. Morisseau C, Hammock BD, (2005). Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu Rev Pharmacol Toxicol 45: 311-333.
23. Motoki A, Merkel MJ, Packwood WH, Cao Z, Liu L, Iliff J, et al. (2008). Soluble epoxide hydrolase inhibition and gene deletion are protective against myocardial ischemia-reperfusion injury in vivo. Am J Physiol Heart Circ Physiol 295: H2128-H2134.
24. Murphy E, Tong H, Steenbergen C, (2003). Preconditioning: is the Akt-ion in the PI3K pathway? J Mol Cell Cardiol 35: 1021-1025.
25. Oudit GY, Penninger JM, (2009). Cardiac regulation by phosphoinositide 3-kinases and PTEN. Cardiovasc Res 82: 250-260.
26. Qiu H, Li N, Liu JY, Harris TR, Hammock BD, Chiamvimonvat N, (2010). Soluble epoxide hydrolase inhibitors and heart failure. Cardiovasc Ther. [Epub ahead of print].
27. Revermann M, Barbosa-Sicard E, Dony E, Schermuly RT, Morisseau C, Geisslinger G, et al. (2009). Inhibition of the soluble epoxide hydrolase attenuates monocrotaline-induced pulmonary hypertension in rats. J Hypertens 27: 322-331.
28. Seubert J, Yang B, Bradbury JA, Graves J, Degraff LM, Gabel S, et al. (2004). Enhanced postischemic functional recovery in CYP2J2 transgenic hearts involves mitochondrial ATP-sensitive K+ channels and p42/p44 MAPK pathway. Circ Res 95: 506-514.
29. Seubert JM, Sinal CJ, Graves J, DeGraff LM, Bradbury JA, Lee CR, et al. (2006). Role of soluble epoxide hydrolase in postischemic recovery of heart contractile function. Circ Res 99: 442-450.
30. Spearman ME, Prough RA, Estabrook RW, Falck JR, Manna S, Leibman KC, et al. (1985). Novel glutathione conjugates formed from epoxyeicosatrienoic acids (EETs). Arch Biochem Biophys 242: 225-230.
31. Spector AA, (2009). Arachidonic acid cytochrome P450 epoxygenase pathway. J Lipid Res 50 (Suppl.): S52-S56.
32. Spector AA, Fang X, Snyder GD, Weintraub NL, (2004). Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Prog Lipid Res 43: 55-90.
33. Stephens L, Anderson K, Stokoe D, Erdjument-Bromage H, Painter GF, Holmes AB, et al. (1998). Protein kinase B kinases that mediate phosphatidylinositol 3,4,5-trisphosphate-dependent activation of protein kinase B. Science 279: 710-714.
34. Suh BC, Hille B, (2008). PIP2 is a necessary cofactor for ion channel function: how and why? Annu Rev Biophys 37: 175-195.
35. Tong H, Imahashi K, Steenbergen C, Murphy E, (2002). Phosphorylation of glycogen synthase kinase-3beta during preconditioning through a phosphatidylinositol-3-kinase-dependent pathway is cardioprotective. Circ Res 90: 377-379.
36. Xie Y, Liu Y, Gong G, Smith DH, Yan F, Rinderspacher A, et al. (2009). Discovery of potent non-urea inhibitors of soluble epoxide hydrolase. Bioorg Med Chem Lett 19: 2354-2359.
37. Yang W, Holmes BB, Gopal VR, Kishore RV, Sangras B, Yi XY, et al. (2007). Characterization of 14,15-epoxyeicosatrienoyl-sulfonamides as 14,15-epoxyeicosatrienoic acid agonists: use for studies of metabolism and ligand binding. J Pharmacol Exp Ther 321: 1023-1031.
38. Zhang Y, El-Sikhry H, Chaudhary KR, Batchu SN, Shayeganpour A, Jukar TO, et al. (2009). Overexpression of CYP2J2 provides protection against doxorubicin-induced cardiotoxicity. Am J Physiol Heart Circ Physiol 297: H37-H46.