4D-QSAR Analysis of a Series of Antifungal P450 Inhibitors and 3D-Pharmacophore Comparisons as a Function of Alignment

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 6, 2003, Pages 2170-2179

  Liu, Jianzhong ^a   Pan, Dahua ^a   Tseng, Yufeng ^a   Hopfinger, Anton J ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENTS; PHARMACORPHORE SITES;

CATALYSTS; COMPUTER SOFTWARE; CORRELATION METHODS; CRYSTAL STRUCTURE; ENZYMES; HYDROGEN BONDS; MEMBRANES; PATHOLOGY;

DRUG THERAPY;

ANTIFUNGAL AGENT; CYTOCHROME P450; ENZYME INHIBITOR;

ALGORITHM; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DRUG ANTAGONISM; PROTEIN CONFORMATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ALGORITHMS; ANTIFUNGAL AGENTS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; MODELS, MOLECULAR; PROTEIN CONFORMATION; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0344254799     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci034142z     Document Type: Article

References (28)

1. Fromtling, R. A. Imidazoles as Medically Important Antifungal Agents: An Overview. Drugs Today 1986, 20, 235-349.
2. D'Arcy, P. F.; Scott, E. M. Antifungal Agents. Prog. Drug Res. 1987, 22, 94-147.
3. Kerridge, D. Antifungal Drugs, Drugs Today 1988, 24, 705-715.
4. Koltin, Y. Target for Antifungal Drug Discovery. Annu. Rep. Med. Chem. 1990, 25, 141-148.
5. Yeagle, P. L.; Martin, R. B.; Lala, A. K.; Lin, H.; Block, K. Differential Effects of Cholesterol and Lanosterol on Artificial Membranes. Proc. Nati. Acad. Sci. U.S.A. 1977, 74, 4924-4926.
6. Vanden Bossche, H.; Bellens, D.; Cools, W.; Gorrens, P. M.; Verhoeven, H.; Willemsens, G.; De Coster, R.; Beerens, D.; Haelterman, C.; Coene, M. C.; Lauwers, W.; Le Jeune, L. Cytochrome P450: Target for Itraconazole. Drug Dev. Res. 1986, 8, 287-298.
7. Hichcock, A.; Brown, B.; Evans, E. G. V.; Adams, D. J. Cytochrome P-450-Dependent 14α-Demethylation of Lanosterol in Candida albicans. Biochem. J. 1989, 260, 549-556.
8. Adams, J. L.; Metcalf, B. W. Therapeutic Consequences of the Inhibition of Sterol Metabolism. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, England, 1990; Vol. 2, pp 333-364.
9. Asai, K.; Tsuchimori, N.; Okonogi, K.; Perfect, J. R.; Gotoh, O.; Yoshida, Y. Formation of Azole-Resistant Candida albicans by Mutation of Sterol 14-Demethylase P450. Antimicrob. Agents Chemother. 1999, 43, 1163-1169.
10. Buchel, K. H.; Draber, W.; Regel, E.; Plempel, M. Synthesen und Eigenschften von Clotrimazol und Weiteren Antimykotischen 1-Triphenylmethylimidazolen (Syntheses and Properties of Clotrimazole and Further Antimycotic 1-(Triphenylmethyl)imidazoles). Arzneim.-Forsch. 1972, 22, 1260-1272.
11. Tafi, A.; Anastassopoulou, J.; Theophanides, T.; Botta, M.; Corelli, F.; Massa, S.; Artico, M.; Costi, R.; Di Santo, R.; Ragno, R. Molecular Modeling of Azole Antifungal Agents Active Against Candida albicans. 1. A Comparative Molecular Field Analysis Study, J. Med. Chem. 1996, 39, 1227-1235.
12. 14αDMInhibiting Azole Antifungal Agents. J. Chem. Inf. Comput. Sci. 1999, 39, 204-210.
13. Tafi, A.; Costi, R.; Botta, M.; Di Santo, R.; Corelli, F.; Massa, S.; Ciacci, A.; Manetti, F. Artico, M. Antifungal Agents, 10, New Derivatives of 1-[(Aryl)[4-aryl-1H-pyrrol-3-yl]methyl]-1H-imidazole, Synthesis, Anti-Candida Activity, and Quantitative Structure Analysis Relationship Studies, J. Med. Chem. 2002, 45, 2720-2732.
14. Ji H.; Zhang, W.; Zhou, Y.; Zhang, M.; Zhu, J.; Song, Y.; Lu, J.; Zhu, J. A Three-Dimensional Model of Lanosterol 14α-Demethylase of Candida albicans and Its Interaction with Azole Antifungals. J. Med. Chem. 2000, 43, 2493-2505.
15. 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.
16. 4D-QSAR User's Manual, Version 3.0, The ChemBats21 Group, Inc., 1780 Wilson Dr., Lake Forest, IL 60045, 2003.
17. HyperChem Program Release 6.03 for Windows; Hypercube, Inc.; 1999.
18. Doherty, D. C. MOLSIM User's Guide, The ChemBats21 Group, Inc., 1780 Wilson Dr., Lake Forest, IL 60045, 1997.
19. Allinger, N. L. Conformational analysis. 130. MM2. A hydrocarbon force field utilizing VI and V2 torsional terms. J. Am. Chem. Soc. 1977, 99, 8127-8134.
20. Hopfinger, A. J.; Pearlstein, R. A. Molecular mechanics force-field parametrization procedures. J. Comput. Chem. 1984, 5, 486-492.
21. Duca, J. S.; Hopfinger, A. J. Estimation of Molecular Similarity Based on 4D-QSAR Analysis: Formalism and Validation J. Chem. Inf. Comput. Sci. 2001, 41, 1367-1387.
22. Krasowski, M. D.; Hong, X.; Hopfinger, A. J.; Harrison, N. L. 4D-QSAR Analysis of a Set of Propofol Analogues: Mapping Binding Sites for an Anesthetic Phenol on the GABAA Receptor. J. Med. Chem. 2002, 45, 3210-3221.
23. Glen, W. G.; Dunn, W. J., III.; Scott, D. R. Principal components analysis and partial least squares. Tetrahedron Comput. Methods 1989, 2, 349-354.
24. 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.
25. 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.
26. Friedman, J. Multivariate adaptive regression splines. Technical Report No. 102; Laboratory for Computational Statistics, Department of Statistics, Stanford University, Stanford, CA, November 1988 (revised August 1990).
27. Brian S. E.; Sabine L.; Morven L. Cluster analysis, 4th ed.; Oxford University Press: 2001.
28. Podust, L. M.; Poulos, T. L.; Waterman, M. R. Crystal Structure of Cytochrome P450 14α-sterol Demethylase (CYP51) from Mycobacterium tuberculosis in Complex with Azole Inhibitors. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 3068-3073.