Evaluation of the inhibitory effect of dihydropyridines on N-type calcium channel by virtual three-dimensional pharmacophore modeling

Arzneimittel-Forschung/Drug Research

Volumn 59, Issue 6, 2009, Pages 283-288

  Ogihara, Takuo ^a   Kano, Takashi ^a   Kakinuma, Chihaya ^a  

^a TAKASAKI UNIVERSITY OF HEALTH AND WELFARE   (Japan)

Author keywords

Amlodipine; Azelnidipine; Benidipine; Calcium channel blockers, dihydropyridine, L type, N type; Cilnidipine; Efonidipine; Nifedipine; Pharmacophore modeling

Indexed keywords

AMLODIPINE; AZELNIDIPINE; BENIDIPINE; CALCIUM CHANNEL N TYPE; CILNIDIPINE; DIHYDROPYRIDINE DERIVATIVE; EFONIDIPINE; NIFEDIPINE; OMEGA CONOTOXIN GVIA;

ARTICLE; CHANNEL GATING; COMPUTER MODEL; IC 50; MOLECULAR MODEL; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

EID: 68549140137     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296398     Document Type: Article

References (28)

1. Levy JH. Management of systemic and pulmonary hypertension. Tex Heart Inst J . 2005;32:467-471
2. Mason RP. Atheroprotective effects of long-acting dihydropyridine- type calcium channel blockers: evidence from clinical trials and basic scientific research. Cerebrovasc Dis . 2003;16Suppl. 3:11-17
3. Sher E, Giovannini F, Codignola A, Passafaro M, Giorgi- Rossi P, Volsen S, et al. Voltage-operated calcium channel heterogeneity in pancreatic beta cells: physiopathological implications. J Bioenerg Biomembr . 2003; 35:687-696 (Pubitemid 38124821)
4. Kameyama A, Kameyama M. [Structure, function and expression of Ca2+ channels]. Nippon Rinsho. 1996;54:672-678
5. Hayashi K, Wakino S, Sugano N, Ozawa Y, Homma K, Saruta T. Ca2+ channel subtypes and pharmacology in the kidney. Circ Res . 2007;16:342-353 (Pubitemid 46272406)
6. Watanabe K, Hosono M, Hayashi Y. Antihypertensive effect of Clinidipine (FRC-8653) in Stroke-Prone Spontaneously Hypertensive rats. Jpn Pharmacol Ther . 1995;23:3001-3011
7. Yamanaka K, Suzuki M, Munehasu S, Ishiko J. [Effect of amlodipine, a new calcium antagonist on isolated blood vessels]. Nippon Yakurigaku Zasshi. 1991;97:167-178
8. Sata T, Mizuno M, Miyama C, Wada Y, Koike H. Pharmacological properties of azelnidipine, a long-acting calcium channel blocker with high-affinity for vascular tissues (Part1)-Calciumchannel blocking actions in receptor binding and isolated blood vessel studies. Jpn Pharmacol Ther . 2002;30:703-709 (Pubitemid 35239033)
9. Karasawa A, Kubo K. Calcium antagonistic effects and the in vitro duration of actions of KW-3049, a new 1,4-dihydropyridine derivative, in isolated canine coronary arteries. Jpn J Pharmacol. 1988;47:35-44. (Pubitemid 18142605)
10. Fleckenstein A. Specific pharmacology of calcium in myocardium, cardiac pacemakers, and vascular smooth muscle. Annu Rev Pharmacol Toxicol. 1977;17:149-166
11. Masuda Y, Iwama T, Yamashita T, Sakai T, Hibi M, Tanaka S, et al. Cardiac and vascular effects of NZ-105, a novel dihydropyridine derivative, in vitro. Arch Int Pharmacodyn Ther . 1991;314:57-73.
12. Fujii S, Kameyama K, Hosono M, Hayashi Y, Kitamura K. Effect of cilnidipine, a novel dihydropyridine Ca++-channel antagonist, on N-type Ca++ channel in rat dorsal root ganglion neurons. J Pharmacol Exp Ther . 1997;280:1184-1191 (Pubitemid 27166712)
13. Unayama H, Maeda K, Domoto H, Yoshimoto R, Inoue K, Akaike N. Cilnidipine blocks N-type Ca2+ channel in acutely dissociated rat sympathetic neurons. Jap J Pharmacol. 1997;73:267.
14. Furukawa T, Yamakawa T, Midera T, Sagawa T, Mori Y, Nukada T. Selectivities of dihydropyridine derivatives in blocking Ca2+ channel subtypes expressed in Xenopus oocytes. J Pharmacol Exp Ther . 1999;291:464-473 (Pubitemid 29503513)
15. Qu YL, Sugiyama K, Ohnuki T, Hattori K, Watanabe K, Nagatomo T. Comparison of binding affinities of x -conotoxin and amlodipine to N-type Ca2+ channels in rat brain. Acta Pharmacol Sin. 1998;19:97-100. (Pubitemid 28123540)
16. Ehlert FJ, Roeske WR, Itoga E, Yamamura HI. The binding of [ 3 H]nitrendipine to receptors for calcium channel antagonists in the heart, cerebral cortex, and ileum of rats. Life Sci. 1982;30:2191-2202
17. Gould RJ, Murphy KM, Snyder SH. [ 3 H]nitrendipine-labeled calcium channels discriminate inorganic calcium agonists and antagonists. Proc Natl Acad Sci USA. 1982;79: 3656-3660 (Pubitemid 12014529)
18. Moresco RM, Govoni S, Battaini F, Trivulzio S, Trabucchi M. Omegaconotoxin binding decreases in aged rat brain. Neurobiol Aging. 1990;11:433-436 (Pubitemid 20274575)
19. Sato K, Park NG, Kohno T, Maeda T, Kim JI, Kato R, Takahashi M. Role of basic residues for the binding of omegaconotoxin GVIA to N-type calciumchannels. Biochem Biophys Res Commun. 1993;194:1292-1296 (Pubitemid 23255022)
20. Kim JI, Takahashi M, Ogura A, Kohno T, Kudo Y, Sato K. Hydroxyl group of Tyr13 is essential for the activity of omega- conotoxin GVIA, a peptide toxin for N-type calcium channel. J Biol Chem. 1994;269:23876-23878 (Pubitemid 2145433)
21. Flinn JP, Pallaghy PK, Lew MJ, Murphy R, Angus JA, Norton RS. Roles of key functional groups in omega-conotoxin GVIA synthesis, structure and functional assay of selected peptide analogues. Eur J Biochem. 1999;262:447-455 (Pubitemid 29266056)
22. Miri R, Javidnia K, Sarkarzadeh H, Hemmateenejad B. Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1,4- dihydropyridines as calciumchannel antagonist. Bioorg Med Chem. 2006;15: 4842-4849 (Pubitemid 44236030)
23. Schleifer KJ. Stereoselective characterization of the 1,4-dihydropyridine binding site at L-type calcium channels in the resting state and the opened/inactivated state. J Med Chem. 1999;42:2204-2211 (Pubitemid 29284239)
24. Yao X, Liu H, Zhang R, Liu M, Hu Z, Panaye A, et al. QSAR and classification study of 1,4-dihydropyridine calcium channel antagonists based on least squares support vector machines. Mol Pharm . 2005;2:348-356 (Pubitemid 41503675)
25. Valentijn K, Tranchand Bunel D, Vaudry H. Omega-conotoxin- and nifedipine-insensitive voltage-operated calcium channels mediate K + -induced release of pro-thyrotropinreleasing hormone-connecting peptides Ps4 and Ps5 from perifused rat hypothalamic slices. Brain Res Mol Brain Res . 1992;14:221-230
26. FavreauP, Gilles N, Lamthanh H, BournaudR, ShimaharaT, Bouet F. et al. A new omega-conotoxin that targets N-type voltage-sensitive calcium channels with unusual specificity. Biochemistry. 2001;40:14567-14575 (Pubitemid 33111740)
27. Villoutreix BO, Renault N, Lagorce D, Sperandio O,Montes M, Miteva MA. Free resources to assist structure-based virtual ligand screening experiments. Curr Protein Pept Sci . 2007;8:381-411. (Pubitemid 47321574)
28. Li H, Yap CW, Ung CY, Xue Y, Li ZR, Han LY, et al. Machine learning approaches for predicting compounds that interact with therapeutic and ADMET related proteins. J Pharm Sci . 2007;96:2838-2860 (Pubitemid 350221187)