Pseudoreceptor models and 3D-QSAR for imidazobenzodiazepines at GABA A/BzR subtypes αxβ3γ2 [x = 1-3, 5, and 6] via Flexible Atom Receptor Model

Journal of Chemical Information and Computer Sciences

Volumn 44, Issue 3, 2004, Pages 1130-1136

  Lu, Aijun ^a   Zhou, Jiaju ^a  

^a INSTITUTE OF PROCESS ENGINEERING   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; COMPUTER AIDED DESIGN; HYDROGEN BONDS; MOLECULAR STRUCTURE; NEUROLOGY; PATIENT TREATMENT;

CENTRAL NERVOUS SYSTEM (CNS); COMPUTER-AIDED DRUG DESIGNS; FLEXIBLE ATOM RECEPTOR MODEL (FLARM); PHARMACOPHORES;

DRUG PRODUCTS;

4 AMINOBUTYRIC ACID A RECEPTOR; BENZODIAZEPINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BENZODIAZEPINES; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, GABA-A;

EID: 3042624115     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci034281g     Document Type: Article

References (42)

1. Chebib, M.; Johnston, G. A. R. GABA-activated ligand gated ion channels: medicinal chemistry and molecular biology. J. Med. Chem. 2000, 43, 1427-1447.
2. A receptors. Brain Res. Rev. 1999, 29, 196-217.
3. Davies, P. A.; Hanna, M. C.; Hales, T. G.; Kirkness, E. F. Insensitivity to anaesthetic agents conferred by a class of GABAA receptor subunit. Nature 1997, 385, 820-823.
4. Sieghart, W. Structure and pharmacology of GABAA receptor subtypes. Pharmacol Rev. 1995, 47(2), 181-234.
5. A receptor populations with novel subunit combinations and drug binding profiles identified in brain by 5- and subunit-specific immunopurification. J. Biol. Chem. 1993, 268, 5965-5973.
6. Benavides, J.; Peny, B.; Ruano, D.; Vitorica, J.; Scatton, B. Comparative autoradiographic distribution on central (benzodiazepine) modulatory site subtypes with high, intermediate, and low affinity for zolpidem and alpidem. Brain Res. 1993, 604, 240-250.
7. 3H]-Ro 15-4513, in cerebellar membranes from two rat lines developed far high and law alcohol sensitivity. J. Neurochern 1990, 54, 1980-1987.
8. 3H]-Ro 15-4513 binding in intact cultured cerebellar granule cells. Eur. J. Pharmacol 1989, 169, 53-60.
9. 3H]-Ro 15-4513 binding sites. Eur. J. Pharm. 1992, 213, 323-329.
10. Wong, G.; Skolnick, P. High affinity ligands for diazepam-insensitive benzodiazepine receptors. Eur. J. Pharm. Mol. Pharm. Sec. 1992, 225, 63-68.
11. A receptor subtype that is insensitive to diazepam. J. Pharmacol. Exp. Ther. 1991, 247, 1236-1242.
12. A receptor-selective for a behavioural alcohol antagonist. Nature 1990, 346, 648-651.
13. A receptors. J. Med. Chem. 1996, 39, 1928-1934.
14. A receptors. Mol. Pharmacol. 1993, 43, 970-975.
15. Whiting, J. G.; Mckernan, R. M.; Iversen, L. L. Another mechanism for creating diversity in γ-aminobutyrate type receptors: RNA splicing directs expression of two forms of γ2 subunit, one of which contains a protein kinase C phosphorylation site. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 9966-9970.
16. Doble, A.; Martin, I. L. Multiple benzodiazepine receptors: no reason for anxiety. Trends Pharmacol. Sci. 1992, 13, 76-81.
17. Jain, A. N.; Dietterich, T. G.; Lathrop, R. H.; Chapman, D.; Critchlow, R. E.; Bauer, B. E.; Webster, T. A.; Lozano-Perez, T. A shape-based machine learning tool for drug design. J. Comput.-Aided Mol. Des. 1994, 8, 635-652.
18. Vedani, A.; Zbinden, P.; Snyder, J. P.; Greenidge, P. A. Pseudoreceptor modeling: the construction of three-dimensional receptor surrogates. J. Am. Chem. Soc. 1995, 117, 4987-4994.
19. Walters, D. E.; Hinds, R. M. Genetically evolved receptor models: A computational approach to construction of receptor models. J. Med. Chem. 1994, 37, 2527-2536.
20. Hahn, M. Receptor surface models. 1. Definition and construction. J. Med. Chem. 1995, 38, 2080-2090.
21. Hahn, M. Receptor surface models. 2. Application to quantitative structure-activity relationships studies. J. Med. Chem. 1995, 38, 2091-2102.
22. Chen, H.; Zhou, J.; Xie, G. PARM: A genetic evolved algorithm to predict bioactivity. J. Chem. Inf. Comput. Sci. 1998, 38, 243-250.
23. Vedani, A.; Zbinden, P. Quasi-atomistic receptor modeling. A bridge between 3D QSAR and receptor fitting. Pharm. Acta Helv. 1998, 73(1), 11-18.
24. Zbinden, P.; Dobler, M.; Folkers, G.; Vedani, A. PrGen: Pseudoreceptor modeling using receptor-mediated ligand alignment and pharmacophore equilibration. Quant. Struct.-Act. Relat. 1998, 17, 122-130.
25. Pei, J.; Zhou, J.; Xie, G.; Chen, H.; He, X. PARM: A practical utility for drug design. J. Mol. Graph. Model. 2001, 19, 448-454.
26. A/benzodiazepine receptor subtype. Med. Chem. Res. 1995, 5, 700-709.
27. Zhang, W.; Koehler, K. F.; Zhang, P.; Cook, J. M. Development of a comprehensive pharmacophore model for the benzodiazepine receptor. Drug Des. Discov. 1995, 12, 193-248.
28. A/Benzodiazepine Receptor Subtypes [αxβ3γ2 (x = 1-3, 5, and 6)] via Comparative Molecular Field Analysis. J. Med. Chem. 1998, 41, 4130-4142.
29. Filizola, M.; Harris, D. L.; Loew, G. H. Development of a 3D Pharmacophore for Nonspecific Ligand Recognition of α1. α2, α3, α5, and α6 Containing GABAA/Benzodiazepine Receptors. Bioorg. Med. Chem. 2000, 8, 1799-1807.
30. SYBYL version 6.5; Tripos Associates: St. Louis. MO 1998.
31. Hempel, A.; Camerman, N.; Camerman, A. Benzodiazepine stereo chemistry: crystal structures of the diazepam antagonist Ro15-1788 and the anomalous benzodiazepine Ro 5-4864. Can. J. Chem. 1987, 65, 1608-1612.
32. Codding, P.; Muir, A. Molecular structure of Ro15-1788 and a model for the binding of benzodiazepine receptor ligands. Structural iden tification of common features in antagonists. Mol. Pharmacol. 1985, 28, 178-184.
33. Wong, G.; Koehler, K. F.; Skolnick, P.; Gu, Z. Q.; Ananthan, S.; Schonholzer, P.; Hunkeler, W.; Zhang, W.; Cook, J. M. Synthetic and computer-assisted analysis of the structural requirements for selective, high affinity ligand binding to diazepam-insensitive benzodiazepine receptors. J. Med. Chem. 1993, 36, 1820-1830.
34. Fryer, R. I.; Zhang, P.; Lin, K. Y.; Upasani, R. B.; Wong, G.; Skolnick, P. Conformational similarity of diazepam-sensitive and insensitive benzodiazepine receptors determined by chiral pyrroloimidazobenzo diazepines. Med. Chem. Res. 1993, 3, 183-191.
35. A/benzodiazepine receptor subsites. Potent affinities of the (S)-enantiomers of framework-constrained 4,5-substituted pyrroloimida zobenzodiazepines. Med. Chem. Res. 1997, 7, 25-35.
36. Haefely, W.; Kyburz, E.; Gerecke, M.; Mohler, H. Recent advances in the molecular pharmacology of benzodiazepine receptors and in the structure-activity relationships of their agonists and antagonists. In Advances in Drug Research; Editor Editors Ed.; Academic Press: New York, 1985; pp 165-322.
37. Ghose, A; Crippen, G. Modeling the benzodiazepine receptor binding site by the general three-dimensional structure-directed quantitative structure-activity relationship method REMOTEDISC. Mol. Phar macol. 1990, 37, 725-734.
38. Crippen, G. Distance geometry analysis of the benzodiazepine binding site. Mol. Pharmacol. 1982, 22, 11-19.
39. Fryer, R. I.; Cook, C.; Gilman, N. W.; Walser, A. Conformational shifts at the benzodiazepine receptor related to the binding of agonists antagonists and inverse agonists. Life Sci. 1986, 39(21), 1947-1957.
40. Borea, P.; Gilli, G.; Bertolasi, V.; Ferretti, V. Stereochemical features controlling binding and intrinsic activity properties of benzodiazepine- receptor ligands. Mol. Pharmacol. 1987, 31, 334-344.
41. Gardner, C. A review of recently developed ligands for neuronal benzodiazepine receptors and their pharmacological activities. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 1992, 16(6), 755-781.
42. Huang, Q.; He, X.; Ma, C.; Liu, R.; Yu, S.; Dayer, C. A.; Wenger, G. R.; Mckernan, R.; Cook, J. M. Pharmacophore/Receptor Models for GABAA/BzR Subtypes α1β3γ2, α6β3γ2, and α6β3γ2) via a Com prehensive Ligand-Mapping Approach. J. Med. Chem. 2000, 43, 71-95.