Leonurine-cysteine analog conjugates as a new class of multifunctional anti-myocardial ischemia agent

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 3996-4009

  Liu, Chunhua ^a   Guo, Wei ^a   Shi, Xueru ^a   Kaium, M A ^a   Gu, Xianfeng ^a   Zhu, Yi Zhun ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Apoptosis; Cardioprotection; Leonurine cysteine analog conjugates

Indexed keywords

3,5 DIMETHOXY 4 (2 AMINO 3 PROP 2 YNYLSULFANYL PROPIONYL) BENZOIC ACID 4 GUANIDINO BUTYL ESTER; 3,5 DIMETHOXY 4 (2 ANIMO 3 ALLYSULFANYL PROPIONYL) BENZOIC ACID 4 GUANIDINO BUTYL ESTER; 3,5 DIMETHOXY 4 (3 (2 CHLOROCARBONYL ETHYLDISULFANYL) PROPIONYL) BENZOIC ACID 4 GUANIDINO BUTYL ESTER; CARDIOVASCULAR AGENT; CASPASE 3; CHLORAMPHENICOL ACETYLTRANSFERASE; CYSTEINE CONJUGATE; HYDROGEN SULFIDE; LEONURINE; PROTEIN BAX; PROTEIN BCL 2; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANIMAL CELL; APOPTOSIS; ARTICLE; CELL PROTECTION; CONTROLLED STUDY; DRUG ACTIVITY; GENE; GENE EXPRESSION; HEART MUSCLE CELL; HEART MUSCLE ISCHEMIA; HEART PROTECTION; HYPOXIA; NONHUMAN; PROTEIN EXPRESSION; RAT; SIGNAL TRANSDUCTION;

ANIMALS; ANIMALS, NEWBORN; BLOTTING, WESTERN; CATALASE; CELLS, CULTURED; CYSTEINE; GALLIC ACID; HEART VENTRICLES; MAGNETIC RESONANCE SPECTROSCOPY; MALONDIALDEHYDE; MASS SPECTROMETRY; MYOCARDIAL ISCHEMIA; POLYMERASE CHAIN REACTION; RATS; SUPEROXIDE DISMUTASE;

EID: 80052943314     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.05.073     Document Type: Article

References (35)

1. Y.Z. Zhu, C.L. Chong, S.C. Chuah, S.H. Huang, H.S. Nai, H.T. Tong, M. Whiteman, and P.K. Moore Cardioprotective effects of nitroparacetamol and paracetamol in acute phase of myocardial infarction in experimental rats Am. J. Physiol-Heart C 290 2006 H517 H524
2. A. Haunstetter, and S. Izumo Apoptosis - basic mechanisms and implications for cardiovascular disease Circ. Res. 82 1998 1111 1129
3. A. Haunstetter, and S. Izumo Toward antiapoptosis as a new treatment modality Circ. Res. 86 2000 371 376
4. S.K. Wattanapitayakul, and J.A. Bauer Oxidative pathways in cardiovascular disease - roles, mechanisms, and therapeutic implications Pharmacol. Therapeut 89 2001 187 206
5. L.J.S. Greenlund, T.L. Deckwerth, and E.M. Johnson Superoxide-dismutase delays neuronal apoptosis - a role for reactive oxygen species in Programmed Neuronal Death Neuron 14 1995 303 315
6. Q. Wang, X.L. Wang, H.R. Liu, P. Rose, and Y.Z. Zhu Protective effects of cysteine analogues on acute myocardial ischemia: novel modulators of endogenous H2S production Antioxid. Redox Signaling 12 2010 1155 1165
7. L. Li, A. Hsu, and P.K. Moore Actions and interactions of nitric oxide, carbon monoxide and hydrogen sulphide in the cardiovascular system and in inflammation - a tale of three gases! Pharmacol. Therapeut 123 2009 386 400
8. B. O'Rourke Pathophysiological and protective roles of mitochondrial ion channels J. Physiology-London 529 2000 23 36
9. T.T. Pan, Z.N. Feng, S.W. Lee, P.K. Moore, and J.S. Bian Endogenous hydrogen sulfide contributes to the cardioprotection by metabolic inhibition preconditioning in the rat ventricular myocytes J. Mol. Cell. Cardiol. 40 2006 119 130
10. K. Hamano, Y. Ikeda, T. Kobayashi, T.S. Li, H. Ito, and A. Mikamo CABG in combination with neovascularization or surgical ventricular restoration for the treatment of severe ischemic heart disease J. Card. Fail. 11 2005 S255
11. R. Morphy, C. Kay, and Z. Rankovic From magic bullets to designed multiple ligands Drug Discov. Today 9 2004 641 651
12. R. Morphy, and Z. Rankovic Designed multiple ligands. An emerging drug discovery paradigm J. Med. Chem. 48 2005 6523 6543
13. A. Gasco, D. Boschi, K. Chegaev, C. Cena, A. Di Stilo, R. Fruttero, L. Lazzarato, B. Rolando, and P. Tosco Multitarget drugs: focus on the NO-donor hybrid drugs Pure Appl. Chem. 80 2008 1693 1701
14. C. Liu, X. Gu, and Y.Z. Zhu Synthesis and biological evaluation of novel leonurine-SPRC conjugate as cardioprotective agents Bioorg. Med. Chem. Lett. 2010
15. X.H. Liu, H. Xin, A.J. Hou, and Y.Z. Zhu Protective effects of leonurine in neonatal rat hypoxic cardiomyocytes and rat infarcted heart Clin. Exp. Pharmacol. P 36 2009 696 703
16. K.P. Loh, J. Qi, B.K. Tan, X.H. Liu, B.G. Wei, and Y.Z. Zhu Leonurine protects middle cerebral artery occluded rats through antioxidant effect and regulation of mitochondrial function Stroke 41 2010 2661 2668
17. Q. Wang, H.R. Liu, Q. Mu, P. Rose, and Y.Z. Zhu S-propargyl-cysteine protects both adult rat hearts and neonatal cardiomyocytes from ischemia/hypoxia injury: the contribution of the hydrogen sulfide-mediated pathway J. Cardiovasc. Pharm. 54 2009 139 146
18. K.F. Cheng, C.S. Yip, H.W. Yeung, and Y.C. Kong Leonurine, an improved synthesis Experientia 35 1979 571 572
19. S.C. Chuah, P.K. Moore, and Y.Z. Zhu S-allylcysteine mediates cardioprotection in an acute myocardial infarction rat model via a hydrogen sulfide-mediated pathway Am. J. Physiol-Heart C 293 2007 H2693 H2701
20. J. Sun, B.K.H. Tan, S.H. Huang, M. Whiteman, and Y.Z. Zhu Effects of natural products on ischemic heart diseases and cardiovascular system Acta Pharmacologica Sinica 23 2002 1142 1151
21. Y.Z. Zhu, S.H. Huang, B.K.H. Tan, J. Sun, M. Whiteman, and Y.C. Zhu Antioxidants in Chinese herbal medicines: a biochemical perspective Nat. Prod. Rep. 21 2004 478 489
22. X.H. Liu, L.L. Pan, P.F. Chen, and Y.Z. Zhu Leonurine improves ischemia-induced myocardial injury through antioxidative activity Phytomedicine 17 2010 753 759
23. B. Freude, T.N. Masters, S. Kostin, F. Robicsek, and J. Schaper Cardiomyocyte apoptosis in acute and chronic conditions Basic Res. Cardiol. 93 1998 85 89
24. X. Liu, L. Pan, Q. Gong, and Y. Zhu Leonurine (SCM-198) improves cardiac recovery in rat during chronic infarction Eur. J. Pharmacol. 649 2010 236 241
25. J. Kajstura, W. Cheng, K. Reiss, W.A. Clark, E.H. Sonnenblick, S. Krajewski, J.C. Reed, G. Olivetti, and P. Anversa Apoptotic and necrotic myocyte cell deaths are independent contributing variables of infarct size in rats Lab. Invest. 74 1996 86 107
26. Z.Q. Zhao, M. Nakamura, N.P. Wang, J.N. Wilcox, S. Shearer, R.S. Ronson, R.A. Guyton, and J. Vinten-Johansen Reperfusion induces myocardial apoptotic cell death Cardiovasc. Res. 45 2000 651 660
27. E.S. Alnemri, D.J. Livingston, D.W. Nicholson, G. Salvesen, N.A. Thornberry, W.W. Wong, and J. Yuan Human ICE/CED-3 protease nomenclature Cell 87 1996 171
28. N.A. Thornberry, and Y. Lazebnik Caspases: enemies within Science 281 1998 1312 1316
29. S.H. Kaufmann, S. Desnoyers, Y. Ottaviano, N.E. Davidson, and G.G. Poirier Specific proteolytic cleavage of poly(ADP-ribose) polymerase: an early marker of chemotherapy-induced apoptosis Cancer Res. 53 1993 3976 3985
30. S. Han, R.A. Moore, and R.E. Viola Synthesis and evaluation of alternative substrates for arginase Bioorg. Chem. 30 2002 81 94
31. H. Yanagisawa, S. Ishihara, A. Ando, T. Kanazaki, S. Miyamoto, H. Koike, Y. Iijima, K. Oizumi, Y. Matsushita, and T. Hata Angiotensin-Converting enzyme-Inhibitors - Perhydro-1,4-Thiazepin-5-One Derivatives J. Med. Chem. 30 1987 1984 1991
32. R.D. Rakhit, R.J. Edwards, J.W. Mockridge, A.R. Baydoun, A.W. Wyatt, G.E. Mann, and M.S. Marber Nitric oxide-induced cardioprotection in cultured rat ventricular myocytes Am. J. Physiol. Heart Circ. Physiol. 278 2000 H1211 H1217
33. P.F. Li, R. Dietz, and R. von Harsdorf Differential effect of hydrogen peroxide and superoxide anion on apoptosis and proliferation of vascular smooth muscle cells Circulation 96 1997 3602 3609
34. L. Li, G. Rossoni, A. Sparatore, L.C. Lee, P. Del Soldato, and P.K. Moore Anti-inflammatory and gastrointestinal effects of a novel diclofenac derivative Free Radic. Biol. Med. 42 2007 706 719
35. T. Kakita, K. Hasegawa, T. Morimoto, S. Kaburagi, H. Wada, and S. Sasayama p300 protein as a coactivator of GATA-5 in the transcription of cardiac-restricted atrial natriuretic factor gene J. Biol. Chem. 274 1999 34096 34102