Attenuation of myocardial ischemia-reperfusion injury by trimetazidine derivatives functionalized with antioxidant properties

Journal of Pharmacology and Experimental Therapeutics

Volumn 317, Issue 3, 2006, Pages 921-928

  Kutala, Vijay Kumar ^a   Khan, Mahmood ^a   Mandal, Rajarsi ^a   Ganesan, Latha P ^a   Tridandapani, Susheela ^a   Kalai, Tamas ^b   Hideg, Kalman ^b   Kuppusamy, Periannan ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF PÉCS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

2,2,5,5 TETRAMETHYL 4 PHENYLPYRROLINYLTRIMETAZIDINE; 2,2,5,5 TETRAMETHYLPYRROLINYLTRIMETAZIDINE; CREATINE KINASE; HO 2921; HO 3630; LACTATE DEHYDROGENASE; MITOGEN ACTIVATED PROTEIN KINASE P38; PEROXY RADICAL; PROTEIN KINASE B; SUPEROXIDE DISMUTASE; TRIMETAZIDINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CARDIOVASCULAR RISK; CONTROLLED STUDY; CORONARY ARTERY BLOOD FLOW; DOSE RESPONSE; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME PHOSPHORYLATION; HEART FUNCTION; HEART HEMODYNAMICS; HEART INFARCTION; HEART LEFT VENTRICLE PRESSURE; HEART MUSCLE ISCHEMIA; HEART PROTECTION; ISOLATED HEART; NONHUMAN; PRIORITY JOURNAL; RAT; REPERFUSION INJURY;

ANIMALS; CARDIOTONIC AGENTS; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FREE RADICAL SCAVENGERS; HEMODYNAMIC PROCESSES; MOLECULAR STRUCTURE; MYOCARDIAL INFARCTION; MYOCARDIAL REPERFUSION INJURY; MYOCARDIUM; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PHOSPHORYLATION; PROTO-ONCOGENE PROTEINS C-AKT; RATS; RATS, SPRAGUE-DAWLEY; SUPEROXIDES; TRIMETAZIDINE;

EID: 33646814422     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.105.100834     Document Type: Article

References (40)

1. Ambrosio G, Zweier JL, Duilio C, Kuppusamy P, Santoro G, Elia PP, Tritto I, Cirillo P, Condorelli M, Chiariello M, et al. (1993) Evidence that mitochondrial respiration is a source of potentially toxic oxygen free radicals in intact rabbit hearts subjected to ischemia and reflow. J Biol Chem 268:18532-18541.
2. Armstrong SC (2004) Protein kinase activation and myocardial ischemia/reperfusion injury. Cardiovasc Res 61:427-436.
3. Brown JM, Terada LS, Grosso MA, Whitman GJ, Velasco SE, Patt A, Harken AH, and Repine JE (1988) Hydrogen peroxide mediates reperfusion injury in the isolated rat heart. Mol Cell Biochem 84:173-175.
4. Charlon V, Boucher F, Clauser P, Harpey C, Favier A, Koukay N, Mouhieddine S, and de Leiris J (1990) Effect of a 5-day trimetazidine pretreatment in a model of ischemic and reperfused isolated rat heart: spin trapping experiments. Adv Exp Med Biol 264:377-382.
5. Das DK, Cordis GA, Rao PS, Liu XK, and Maity S (1991) High-performance liquid chromatographic detection of hydroxylated benzoic acids as an indirect measure of hydroxyl radical in heart: its possible link with the myocardial reperfusion injury. J Chromatogr 536:273-282.
6. Das DK, Maulik N, Yoshida T, Engelman RM, and Zu YL (1996) Preconditioning potentiates molecular signaling for myocardial adaptation to ischemia. Ann NY Acad Sci 793:191-209.
7. Dennis SC, Gevers W, and Opie LH (1991) Protons in ischemia: where do they come from; where do they go to? J Mol Cell Cardiol 23:1077-1086.
8. Ganesan LP, Wei G, Pengal RA, Moldovan L, Moldovan N, Ostrowski MC, and Tridandapani S (2004) The serine/threonine kinase Akt promotes Fc γ receptor-mediated phagocytosis in murine macrophages through the activation of p70S6 kinase. J Biol Chem 279:54416-54425.
9. Gelvan D, Saltman P, and Powell SR (1991) Cardiac reperfusion damage prevented by a nitroxide free radical. Proc Natl Acad Sci USA 88:4680-4684.
10. Goldstein S, Merenyi G, Russo A, and Samuni A (2003) The role of oxoammonium cation in the SOD-mimic activity of cyclic nitroxides. J Am Chem Soc 125:789-795.
11. Griendling KK, Ushio-Fukai M, Lassegue B, and Alexander RW (1997) Angiotensin II signaling in vascular smooth muscle: new concepts. Hypertension 29:366-373.
12. Guarnieri C and Muscari C (1993) Effect of trimetazidine on mitochondrial function and oxidative damage during reperfusion of ischemic hypertrophied rat myocardium. Pharmacology 46:324-331.
13. Harpery C, Clauser P, Labrid C, Freyria JL, and Poirier JP (1989) Trimetazidine, a cellular anti-ischemic agent. Cardiovasc Drug Rev 1989:292-312.
14. Hausenloy DJ, Tsang A, and Yellon DM (2005) The reperfusion injury salvage kinase pathway: a common target for both ischemic preconditioning and postconditioning. Trends Cardiovasc Med 15:69-75.
15. Hausenloy DJ and Yellon DM (2004) New directions for protecting the heart against ischaemia-reperfusion injury: targeting the reperfusion injury salvage kinase (RISK) pathway. Cardiovasc Res 61:448-460.
16. Kalai T, Khan M, Balog M, Kutala VK, Kuppusamy P, and Hideg K (2006) Structure and antioxidant activity relationship of trimetazidine derivatives. Bioorg Med Chem, in press.
17. Kantor PF, Lucien A, Kozak R, and Lopaschuk GD (2000) The antianginal drug trimetazidine shifts cardiac energy metabolism from fatty acid oxidation to glucose oxidation by inhibiting mitochondrial long-chain 3-ketoacyl coenzyme A thiolase. Circ Res 86:580-588.
18. Khan M, Varadharaj S, Ganesan LP, Shobha JC, Naidu MU, Tridandapani S, Parinandi NL, Kutala VK, and Kuppusamy P (2006) C-phycocyanin protects against ischemia-reperfusion injury of heart through involvement of p38 MAPK and ERK signaling. Am J Physiol, in press.
19. Kloner RA, Przyklenk K, and Whittaker P (1989) Deleterious effects of oxygen radicals in ischemia/reperfusion: resolved and unresolved issues. Circulation 80:1115-1127.
20. .- or as SOD mimics? J Biol Chem 271:26026-26031.
21. Kukreja RC and Hess ML (1992) The oxygen free radical system: from equations through membrane-protein interactions to cardiovascular injury and protection. Cardiovasc Res 26:641-655.
22. Li H, Xu KY, Zhou L, Kalai T, Zweier JL, Hideg K, and Kuppusamy P (2000) A pyrroline derivative of mexiletine offers marked protection against ischemia/reperfusion-induced myocardial contractile dysfunction. J Pharmacol Exp Ther 295:563-571.
23. Liu HR, Gao F, Tao L, Yan WL, Gao E, Christopher TA, Lopez BL, Hu A, and Ma XL (2004) Antiapoptotic mechanisms of benidipine in the ischemic/reperfused heart. Br J Pharmacol 142:627-634.
24. Lopaschuk GD, Barr R, Thomas PD, and Dyck JR (2003) Beneficial effects of trimetazidine in ex vivo working ischemic hearts are due to a stimulation of glucose oxidation secondary to inhibition of long-chain 3-ketoacyl coenzyme a thiolase. Circ Res 93:e33-e37.
25. Ma XL, Kumar S, Gao F, Louden CS, Lopez BL, Christopher TA, Wang C, Lee JC, Feuerstein GZ, and Yue TL (1999) Inhibition of p38 mitogen-activated protein kinase decreases cardiomyocyte apoptosis and improves cardiac function after myocardial ischemia and reperfusion. Circulation 99:1685-1691.
26. Miller FJ Jr, Gutterman DD, Rios CD, Heistad DD, and Davidson BL (1998) Superoxide production in vascular smooth muscle contributes to oxidative stress and impaired relaxation in atherosclerosis. Circ Res 82:1298-1305.
27. Niki E (1999) Free radical initiators as a source of water- or lipid-soluble peroxyl radicals. Methods Enzymol 186:B100-B108.
28. Omura T, Yoshiyama M, Shimada T, Shimizu N, Kim S, Iwao H, Takeuchi K, and Yoshikawa J (1999) Activation of mitogen-activated protein kinases in in vivo ischemia/reperfused myocardium in rats. J Mol Cell Cardiol 31:1269-1279.
29. Pantos C, Bescond-Jacquet A, Tzeis S, Paizis I, Mourouzis I, Moraitis P, Malliopoulou V, Politi ED, Karageorgiou H, Varonos D, et al. (2005) Trimetazidine protects isolated rat hearts against ischemia-reperfusion injury in an experimental timingdependent manner. Basic Res Cardiol 100:154-160.
30. Samuni A, Winkelsberg D, Pinson A, Hahn SM, Mitchell JB, and Russo A (1991) Nitroxide stable radicals protect beating cardiomyocytes against oxidative damage. J Clin Investig 87:1526-1530.
31. Shankar RA, Hideg K, Zweier JL, and Kuppusamy P (2000) Targeted antioxidant properties of N-[(tetramethyl-3-pyrroline-3-carboxamido)propyl] phthalimide and its nitroxide metabolite in preventing postischemic myocardial injury. J Pharmacol Exp Ther 292:838-845.
32. Shimizu N, Yoshiyama M, Omura T, Hanatani A, Kim S, Takeuchi K, Iwao H, and Yoshikawa J (1998) Activation of mitogen-activated protein kinases and activator protein-1 in myocardial infarction in rats. Cardiovasc Res 38:116-124.
33. Sumida T, Otani H, Kyoi S, Okada T, Fujiwara H, Nakao Y, Kido M, and Imamura H (2005) Temporary blockade of contractility during reperfusion elicits a cardioprotective effect of the p38 MAP kinase inhibitor SB-203580. Am J Physiol 288:H2726-H2734.
34. Takada Y, Hashimoto M, Kasahara J, Aihara K, and Fukunaga K (2004) Cytoprotective effect of sodium orthovanadate on ischemia/reperfusion-induced injury in the rat heart involves Akt activation and inhibition of fodrin breakdown and apoptosis. J Pharmacol Exp Ther 311:1249-1255.
35. Toth A, Halmosi R, Kovacs K, Deres P, Kalai T, Hideg K, Toth K, and Sumegi B (2003) Akt activation induced by an antioxidant compound during ischemiareperfusion. Free Radic Biol Med 35:1051-1063.
36. Tritto I, Wang P, Kuppusamy P, Giraldez R, Zweier JL, and Ambrosio G (2005) The anti-anginal drug trimetazidine reduces neutrophil-mediated cardiac reperfusion injury. J Cardiovasc Pharmacol 46:89-98.
37. Walker DM, Pasini E, Kucukoglu S, Marber MS, Iliodromitis E, Ferrari R, and Yellon DM (1993) Heat stress limits infarct size in the isolated perfused rabbit heart. Cardiovasc Res 27:962-967.
38. Weiss JN, Korge P, Honda HM, and Ping P (2003) Role of the mitochondrial permeability transition in myocardial disease. Circ Res 93:292-301.
39. Yue TL, Ma XL, Wang X, Romanic AM, Liu GL, Louden C, Gu JL, Kumar S, Poste G, Ruffolo RR Jr, et al. (1998) Possible involvement of stress-activated protein kinase signaling pathway and Fas receptor expression in prevention of ischemia/reperfusion-induced cardiomyocyte apoptosis by carvedilol. Circ Res 82:166-174.
40. Yue TL, Wang C, Gu JL, Ma XL, Kumar S, Lee JC, Feuerstein GZ, Thomas H, Maleeff B, and Ohlstein EH (2000) Inhibition of extracellular signal-regulated kinase enhances ischemia/reoxygenation-induced apoptosis in cultured cardiac myocytes and exaggerates reperfusion injury in isolated perfused heart. Circ Res 86:692-699.