3D-QSAR CoMFA/CoMSIA models based on theoretical active conformers of HOE/BAY-793 analogs derived from HIV-1 protease inhibitor complexes

European Journal of Medicinal Chemistry

Volumn 44, Issue 11, 2009, Pages 4344-4352

  da Cunha, Elaine Fontes Ferreira ^a,b,c   Sippl, Wolfgang ^b   de Castro Ramalho, Teodorico ^a   Ceva Antunes, Octavio Augusto ^c   de Alencastro, Ricardo Bicca ^c   Albuquerque, Magaly Girão ^c  

^a FEDERAL UNIVERSITY OF LAVRAS   (Brazil)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

3D QSAR CoMFA CoMSIA; Aspartyl protease; C2 Symmetric diol; HIV 1 protease inhibitor HOE BAY 793; Molecular modeling; Peptidomimetic

Indexed keywords

HOE BAY 793 DERIVATIVE; PEPTIDOMIMETIC AGENT; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; ELECTRICITY; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 70349770582     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.05.016     Document Type: Article

References (31)

1. Wlodawer A., and Erickson J.W. Annu. Rev. Biochem. 62 (1993) 543-585
2. Harte Jr. W.E., Swaminathan S., Mansuri M.M., Martin J.C., Rosenberg I.E., and Beveridge D.L. Proc. Natl. Acad. Sci. U S A 87 (1990) 8864-8868
3. Scott W.R.P., and Schiffer C.A. Structure 8 (2000) 1259-1265
4. de Clercq E. J. Med. Chem. 48 (2005) 1297-1313
5. Budt K.H., Peyman A., Hansen J., Knolle J., Meichsner C., Paessens A., Ruppert D., and Stowasser B. Bioorg. Med. Chem. 3 (1995) 559-571
6. Garg R., Gupta S.P., Gao H., Babu M.S., Debnath A.K., and Hansch C. Chem. Rev. 99 (1999) 3525-3602
7. Gayathri P., Pande V., Sivakumar R., and Gupta S.P. Bioorg. Med. Chem. 9 (2001) 3059-3063
8. Cramer III R.D., Patterson D.E., and Bunce J.D. J. Am. Chem. Soc. 110 (1988) 5959-5967
9. Klebe G., Abraham U., and Meitzner T. J. Med. Chem. 37 (1994) 4130-4146
10. Sippl W., and Holtje H.D. J. Mol. Struct. (Theochem) 503 (2000) 31-50
11. Sippl W. J. Comput. Aided Mol. Des. 16 (2002) 825-830
12. da Cunha E.F.F., Albuquerque M.G., Antunes O.A.C., and de Alencastro R.B. QSAR Comb. Sci. 24 (2005) 240-253
13. SYBYL 6.22, TRIPOS International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA 2001.
14. Lange-Savage G., Berchtold H., Liesum A., Budt K.H., Peyman A., Knolle J., Sedlacek J., Fabry M., and Hilgenfeld R. Eur. J. Biochem. 248 (1997) 313-322
15. Gasteiger J., and Marsili M. Tetrahedron 36 (1980) 3219-3228
16. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902-3909
17. Halgren T.A. J. Comput. Chem. 17 (1996) 490-519
18. Perkins R., Fang H., Tong W., and Welsh W.J. Environ. Toxicol. Chem. 22 (2003) 1666-1679
19. Folkers G., Merz A., and Rognan D. In: Kubinyi H. (Ed). 3D-QSAR in Drug Design. Theory, Methods and Applications (1993), ESCOM, Leiden, The Netherlands 583-618
20. Viswanadhan V.N., Ghose A.K., Revankar G.R., and Robins R.K. J. Chem. Inf. Comput. Sci. 29 (1989) 163-172
21. Kamath S., and Buolamwini J.K. J. Med. Chem. 46 (2003) 4657-4668
22. Bohm M., Sturzebecher J., and Klebe G. J. Med. Chem. 42 (1999) 458-477
23. Hou T.J., Li Z.M., Li Z., Liu J., and Xu X.J. J. Chem. Inf. Comput. Sci. 40 (2000) 1002-1009
24. Hou T.J., Zhu L.L., Chen L.R., and Xu X.J. J. Chem. Inf. Comput. Sci. 43 (2003) 273-287
25. Burkert U., and Allinger N.L. Molecular Mechanics, ACS Monograph 177 (1982), American Chemical Society, Washington
26. Dreyer G.B., Boehm J.C., Chenera B., DesJarlais R.L., Hassell A.M., Meek T.D., Tomaszek Jr. T.A., and Lewis M. Biochemistry 32 (1993) 937-947
27. Hopfinger A.J., Wang S., Tokarski J.S., Jin B., Albuquerque M.G., Madhav P.J., and Duraiswami C. J. Am. Chem. Soc. 119 (1997) 10509-10524
28. Albuquerque M.G., Hopfinger A.J., Barreiro E.J., and de Alencastro R.B. J. Chem. Inf. Comput. Sci. 38 (1998) 925-938
29. Ravi M., Hopfinger A.J., Hormann R.E., and Dinan L. J. Chem. Inf. Comput. Sci. 41 (2001) 1587-1604
30. Pan D.H., Tseng Y.F., and Hopfinger A.J. J. Chem. Inf. Comput. Sci. 43 (2003) 1591-1607
31. Hong X., and Hopfinger A.J. J. Chem. Inf. Comput. Sci. 43 (2003) 324-336