3D-pharmacophores of flavonoid binding at the benzodiazepine GABAA receptor site using 4D-QSAR analysis

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 1, 2003, Pages 324-336

  Hong, Xuan ^a   Hopfinger, A J ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOBUTYRIC ACID; FLAVONOID;

COMPUTER SIMULATION; CONFORMATIONS; DRUG PRODUCTS; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; OPTIMIZATION; QUANTUM THEORY;

CHEMICAL BONDS;

4 AMINOBUTYRIC ACID A RECEPTOR; FLAVONOID; LIGAND;

ARTICLE; BINDING SITE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; DRUG DESIGN; METABOLISM; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BINDING SITES; COMPUTER SIMULATION; DRUG DESIGN; FLAVONOIDS; LIGANDS; MODELS, CHEMICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, GABA-A;

EID: 0037208269     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci0200321     Document Type: Article

References (33)

1. A receptor agonists, partial agonists and antagonists. The GABA receptors, 2nd ed; Enna, S. J., Bowery, Norman G., Eds.; 1997.
2. A receptors". TIPS 1995, 16, 162-168.
3. Woods, J. H.; Katz, J. L.; Winger, G. Benzodiazepines: use, abuse and consequences. Pharmacol. Rev. 1992, 44, 151-347.
4. Medina, J. H.; Viola, H.; Wolfman, C.; Marder, M.; Wasowski, C.; Calvo, D.; Paladini, A. C. Overview - flavonoids: a new family of benzodiazepine receptor ligands. Neurochem. Res. 1997, 22(4), 419-425.
5. Marder, M.; Viola, H.; Wasowski, C.; Waterman, P. G.; Cassels, B. K.; Medina, J. H.; Paladini, A. C. 6-Bromoflavone, a high affinity ligand for the central benzodiazepine receptors is member of a family of active flavonoids. Biochem. Biophys. Res. Commun. 1996, 223(2), 384-389.
6. Haberlin, H.; Tschiersch, K. P.; Schafer, H. L. Flavonoids from Leptospermum scoparium with affinity to the benzodiazepine receptor characterized by structure activity relationships and in vivo studies of a plant extract. Pharmazie 1994, 49, 912-921.
7. Shen, X.-L.; Nielsen, M.; Witt, M. R.; Sterner, O.; Bergendorff, O.; Khayyal, M. Inhibition of [methyl-3H] diazepam binding to rat brain membranes in vitro by dinatin and skrofulein. Acta Pharmacol. Sinica. 1994, 15, 385-388.
8. A receptor complex. J. Med. Chem. 1999, 42, 4343-4350.
9. A receptor complex. Bioorg. Med. Chem. 2001, 9, 323-335.
10. A receptors. J. Med. Chem. 2001, 44, 1883-1891.
11. A receptor. J. Med. Chem. 2002. 45, 4188-4201.
12. Hopfinger, A. J.; Wang, S.; Tokarski, J. S.; Jin, B.; Albuquerque, M.; Madhav, P. J.; Duraiswami, C. Construction of 3D-QSAR models using the 4D-QSAR analysis formalism. J. Am. Chem. Soc. 1997, 119, 10509-10524.
13. Venkatarangan, P.; Hopfinger, A. J. Prediction of ligand-receptor binding free energy by 4D-QSAR analysis: application to a set of glucose analogue inhibitors of glycogen phosphorylase. J. Chem. Inf. Comput. Sci. 1999, 39, 1141-1150.
14. 2 receptor antagonists. J. Chem. Inf. Comput. Sci. 1998, 38, 925-938.
15. Ravi, M.; Hopfinger, A. J.; Hormann, R. E.; Dinan, L. 4D-QSAR analysis of a set of ecdysteroids and a comparison to CoMFA modeling. J. Chem. Inf. Comput. Sci. 2001, 41, 1587-1604.
16. A receptor. J. Med. Chem. 2002, 45, 3210-3221.
17. Vedani, A.; Briem, H.; Dobler, M.; Dollinger, K.; McMasters, D. R. Multiple conformation and protonation-state representation in 4D-QSAR: The neurokinin-1 receptor system. J. Med. Chem. 2000, 43, 4416-4427.
18. Vedani, A.; McMasters, D. R.; Dobler, M. Multi-conformational ligand representation in 4D-QSAR: Reducing the bias associated with ligand alignment. Quant. Struct.-Act. Relat. 2000, 19, 149-161.
19. Streich, D.; Neuburger-Zehnder, M.; Vedani, A. Induced fit - The key for understanding LSD activity. A 4D-QSAR study on the 5-HT2A receptor system. Quant. Struct.-Act. Relat. 2000, 19, 563-573.
20. HyperChem Program Release 5.01 for Windows; Hypercube, Inc.; 1996.
21. Doherty, D. C. MOLSIM User's Guide, The Chem21 Group, Inc., 1780 Wilson Dr., Lake Forest, IL 60045, 1997.
22. Allinger, N. L. Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms. J. Am. Chem. Soc. 1977, 99, 8127-8134.
23. Hopfinger, A. J.; Pearlstein, R. A. Molecular mechanics force-field parametrization precedures. J. Comput. Chem. 1984, 5, 486-492.
24. Glen, W. G.; Dunn, W. J., III; Scott, D. R. Principal components analysis and partial least squares. Tetrahedron Comput. Methods. 1989. 2, 349-354.
25. 4D-QSAR User's Manual, Version 2.0, The Chem21 Group, Inc., 1780 Wilson Dr., Lake Forest, IL 60045, 1997.
26. Rogers, D. G/SPLINES; A hybrid of Friedman's multivariate adaptive regression splines (MARS) algorithm with Holland's genetic algorithm. The Proceedings of the Fourth International Conference on Genetic Algorithm; San Diego, 1991; pp. 38-46.
27. Rogers, D.; Hopfinger, A. J. Application of genetic function approximation to quantitative structure - activity relationships and quantitative structure - property relationships. J. Chem. Inf. Comput. Sci. 1994, 34, 854-866.
28. Friedman, J. Multivariate adaptive regression splines. Technical Report No. 102; Laboratory for Computational Statistics, Department of Statistics, Stanford University, Stanforf, CA, November 1988 (revised August 1990).
29. Walters, W. P.; Stahl, M. T.; Murcko, M. A. Virtual screening - an overview. Drug Discovery Today 1998, 3, 160-194.
30. Hopfinger, A. J.; Reaka, A.; Venkatarangan, P.; Duca, J. S.; Wang, S. Construction of a virtual high throughput screen by 4D-QSAR analysis: application to a combinatorial library of glucose inhibitors of glycogen phosphorylase b. J. Chem. Inf. Comput. Sci. 1999, 39, 1151-1160.
31. Rossi, M.; Rickles, L. F.; Halpin, W. A. The crystal and molecular structure of quercetin: A biologically active and naturally occurring flavonoid. Bioorg. Chem. 1986, 14, 55-69.
32. Rossi, M.; Meyer, R.; Constantinou, P.; Caruso, F.; Castelbuono, D.; O'Brien, M.; Narasimhan, V. Molecular structure and activity toward DNA of baicalein, a flavone constituent of the Asian herbal medicine "Sho-saiko-to". J. Nat. Prod. 2001, 64, 26-31.
33. Ishiki, H. M.; Alemán, C.; Galembeck, S. E. Conformational preferences of flavone and isoflavone in the gas phase, aqueous solution and organic solution. Chem. Phys. Lett. 1998, 287, 579-584.