Different pharmacological properties of the optical isomers of MN9202, a novel 1,4-dihydropyridine Ca 2+ channel modulator, in rat ventricular myocytes

Clinical and Experimental Pharmacology and Physiology

Volumn 37, Issue 8, 2010, Pages 817-825

  Li, Xiao Qiang ^a   Cao, Wei ^a   Zeng, Ai Guo ^c   Yang, Zhi Fu ^b   Xing, Bin ^a   Dong, Ling ^a   Zhang, Hai Feng ^a   Mei, Qi Bing ^a  

^a FOURTH MILITARY MEDICAL UNIVERSITY   (China)

^b FOURTH MILITARY MEDICAL UNIVERSITY   (China)

^c XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

calcium channel blocker; cardiomyocytes; contraction; enantiomers; L type Ca 2+ channel

Indexed keywords

1,4 DIHYDRO 2,6 DIMETHYL 4 (3 NITROPHENYL) 3,5 PYRIDINEDICARBOXYLIC ACID METHYL PENTYL ESTER; 1,4 DIHYDROPYRIDINE DERIVATIVE; CALCIUM CHANNEL; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM CURRENT; CHIRALITY; CONTROLLED STUDY; DEPOLARIZATION; ENANTIOMER; EVALUATION; HEART VENTRICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; KINETICS; MUSCLE CELL; MUSCLE CONTRACTILITY; NONHUMAN; RAT; STEADY STATE;

ALGORITHMS; ANIMALS; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS, L-TYPE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIHYDROPYRIDINES; ELECTROPHYSIOLOGY; KINETICS; MALE; MYOCARDIAL CONTRACTION; MYOCYTES, CARDIAC; NITROBENZENES; PATCH-CLAMP TECHNIQUES; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955115026     PISSN: 03051870     EISSN: 14401681     Source Type: Journal    
DOI: 10.1111/j.1440-1681.2010.05381.x     Document Type: Article

References (32)

1. Geison GL, Secord JA. Pasteur and the process of discovery. The case of optical isomerism. Isis 1988 79:6 36.
2. Ilisz I, Berkecz R, Peter A. Application of chiral derivatizing agents in the high-performance liquid chromatographic separation of amino acid enantiomers: A review. J. Pharm. Biomed. Anal. 2008 47:1 15.
3. De Camp WH. Chiral drugs: The FDA perspective on manufacturing and control. J. Pharm. Biomed. Anal. 1993 11:1167 1172.
4. Franckowiak G, Bechem M, Schramm M, Thomas G. The optical isomers of the 1,4-dihydropyridine BAYK 8644 show opposite effects on Ca channels. Eur. J. Pharmacol. 1985 114:223 226.
5. Artigas P, Ferreira G, Reyes N, Brum G, Pizarro G. Effects of the enantiomers of BayK 8644 on the charge movement of L-type Ca channels in guinea-pig ventricular myocytes. J. Membr. Biol. 2003 193:215 227.
6. Mikus G, Mast V, Ratge D, Wisser H, Eichelbaum M. Stereoselectivity in cardiovascular and biochemical action of calcium antagonists: Studies with the enantiomers of the dihydropyridine nitrendipine. Clin. Pharmacol. Ther. 1995 57:52 61.
7. Yang ZF, Zhou SY, Mei QB, Yang TH, Liu ZG. Metabolic kinetics of MN9202 in beagle dog liver microsomes. Acta Pharmacol. Sin. 2005 40:1019 1023.
8. Yang ZF, Zhou SY, Yang TH, Liu XY, Mei QB. Pharmacokinetics of the analogs at C3 and C5 of m-nifedipine in beagle dogs. Biopharm. Drug Dispos. 2008 29:485 494.
9. Mi M, Hu YZ, Zhang QH, Zhu XX, Zhao YF, Mei QB. Effects of calcium channel blocker MN9202 on hemodynamics of rabbits. Chin. Heart J. 2005 17:106 108.
10. Susic D, Varagic J, Frohlich ED. Pharmacologic agents on cardiovascular mass, coronary dynamics and collagen in aged spontaneously hypertensive rats. J. Hypertens. 1999 17:1209 1215. (Pubitemid 29389570)
11. Nayler WG, Liu JJ, Panagiotopoulos S. Nifedipine and experimental cardioprotection. Cardiovasc. Drugs Ther. 1990 4 (Suppl. 5 879 885.
12. Gaviraghi G, Micheli D, Trist DG. Recent developments in the use of calcium antagonists in myocardial protection. Pharmacol. Res. 1995 31:251 254.
13. Inomata K, Tanaka H. Protective effect of benidipine against sodium azide-induced cell death in cultured neonatal rat cardiac myocytes. J. Pharmacol. Sci. 2003 93:163 170.
14. Zhu X, Zhu X, Niu X et al. Inhibition of cardiomyocyte contractile/relaxation by MN9202 and mechanisms involved. Arch. Med. Res. 2008 39:489 495.
15. Li XQ, Zhao MG, Mei QB et al. Effects of tumor necrosis factor-alpha on calcium movement in rat ventricular myocytes. Acta Pharmacol. Sin. 2003 24:1224 1230.
16. Ren J, Wold LE. Measurement of cardiac mechanical function in isolated ventricular myocytes from rats and mice by computerized video-based imaging. Biol. Proced. Online 2001 3:43 53.
17. 2+ channel in ventricular myocytes. J. Appl. Physiol. 2002 93:1660 1668.
18. Li XQ, Zheng YM, Rathore R, Ma J, Takeshima H, Wang YX. Genetic evidence for functional role of ryanodine receptor 1 in pulmonary artery smooth muscle cells. Pflügers Arch. 2009 457:771 783.
19. Fischer C, Schönberger F, Mück W, Heuck K, Eichelbaum M. Simultaneous assessment of the intravenous and oral disposition of the enantiomers of racemic nimodipine by chiral stationary-phase high-performance liquid chromatography and gas chromatography/ mass spectroscopy combined with a stable isotope technique. J. Pharm. Sci. 1993 82:244 250.
20. i. Am. J. Physiol. 1995 268:C271 7.
21. Bers DM, Perez-Reyes E. Ca channels in cardiac myocytes. Structure and function in Ca influx and intracellular Ca release. Cardiovasc. Res. 1999 42:339 360.
22. Bers DM. Cardiac excitation-contraction coupling. Nature 2002 415:198 205.
23. 2+ channel remodels its own signalling pathway in cardiac cells. Prog. Biophys. Mol. Biol. 2006 90:118 135.
24. 2+ channel: Model construction and docking calculations. J. Med. Chem. 2007 50:1504 1513.
25. Kojda G, Klaus W, Werner G, Fricke U. The influence of 3-ester side chain variation on the cardiovascular profile of nitrendipine in porcine isolated trabeculae and coronary arteries. Naunyn Schmiedebergs Arch. Pharmacol. 1991 344:488 494.
26. 2+ channels and ryanodine receptors in heart cells. Nature 2001 410:592 596.
27. Liew R, Stagg MA, MacLeod KT, Collins P. Raloxifene acutely suppresses ventricular myocyte contractility through inhibition of the L-type calcium current. Br. J. Pharmacol. 2004 142:89 96.
28. Pietrobon D, Hess P. Novel mechanism of voltage-dependent gating in L-type calcium channels. Nature 1990 346:651 655.
29. Bean BP. Nitrendipine block of cardiac calcium channels: High-affinity binding to the inactivated state. Proc. Natl Acad. Sci. USA 1984 81:6388 6392.
30. Sanguinetti MC, Kass RS. Voltage-dependent block of calcium channel current in the calf cardiac Purkinje fiber by dihydropyridine calcium channel antagonists. Circ. Res. 1984 55:336 348.
31. Snyders DJ, Hondeghem LM. Effects of quinidine on the sodium current of guinea pig ventricular myocytes. Evidence for a drug-associated rested state with altered kinetics. Circ. Res. 1990 66:565 579.
32. Huang Z, Shi G, Gao F et al. Effects of N-n-butyl haloperidol iodide on L-type calcium channels and intracellular free calcium in rat ventricular myocytes. Biochem. Cell Biol. 2007 85:182 188. (Pubitemid 46841686)