Docking and 3D-QSAR studies of BMS-806 analogs as HIV-1 gp120 entry inhibitors

European Journal of Medicinal Chemistry

Volumn 44, Issue 9, 2009, Pages 3524-3532

  Teixeira, C ^a   Serradji, N ^a   Maurel, F ^a   Barbault, F ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

3D QSAR; CoMFA; CoMSIA; Docking; gp120 inhibitors

Indexed keywords

4 BENZOYL 1 [(4 METHOXY 1H PYRROLO[2,3 B]PYRIDIN 3 YL)OXOACETYL] 2 METHYLPIPERAZINE; BMS 043; CD4 ANTIGEN; GLYCOPROTEIN GP 120; LIGAND; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; DRUG CONFORMATION; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; HOST CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; IC 50; LIGAND BINDING; MOLECULAR DOCKING; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY; STEREOSPECIFICITY; VIRUS INHIBITION;

ANTI-HIV AGENTS; COMPUTER SIMULATION; HIV ENVELOPE PROTEIN GP120; HIV-1; MODELS, MOLECULAR; PIPERAZINES; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67650395305     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.03.028     Document Type: Article

References (39)

1. Kwong P.D., Wyatt R., Robinson J., Sweet R.W., Sodroski J., and Hendrickson W.A. Nature 393 (1998) 648-659
2. Borkow G., and Lapidot A. Curr. Drug Targets Infect. Disord. 5 (2005) 3-15
3. Harrison S.C. Adv. Virus Res. 64 (2005) 231-261
4. Blair W.S., Lin P.F., Meanwell N.A., and Wallace O.B. Drug Discov. Today 5 (2000) 183-194
5. Moore J.P., and Doms R.W. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 10598-10602
6. Huang C.C., Tang M., Zhang M.Y., Majeed S., Montabana E., Stanfield R.L., Dimitrov D.S., Korber B., Sodroski J., Wilson I.A., Wyatt R., and Kwong P.D. Science 310 (2005) 1025-1028
7. Kwong P.D., Wyatt R., Majeed S., Robinson J., Sweet R.W., Sodroski J., and Hendrickson W.A. Structure 8 (2000) 1329-1339
8. Wyatt R., Kwong P.D., Desjardins E., Sweet R.W., Robinson J., Hendrickson W.A., and Sodroski J.G. Nature 393 (1998) 705-711
9. Vermeire K., and Schols D. Expert Opin. Investig. Drugs 14 (2005) 1199-1212
10. Berchanski A., and Lapidot A. Biochim. Biophys. Acta 1768 (2007) 2107-2119
11. Borkow G., Vijayabaskar V., Lara H.H., Kalinkovich A., and Lapidot A. Antiviral Res. 60 (2003) 181-192
12. Cabrera C., Gutierrez A., Barretina J., Blanco J., Litovchick A., Lapidot A., Clotet B., and Este J.A. Antiviral Res. 53 (2002) 1-8
13. Catani M.V., Corasaniti M.T., Ranalli M., Amantea D., Litovchick A., Lapidot A., and Melino G. J. Neurochem. 84 (2003) 1237-1245
14. Hegde R., Borkow G., Berchanski A., and Lapidot A. FEBS J. 274 (2007) 6523-6536
15. Guo Q., Ho H.T., Dicker I., Fan L., Zhou N., Friborg J., Wang T., McAuliffe B.V., Wang H.G., Rose R.E., Fang H., Scarnati H.T., Langley D.R., Meanwell N.A., Abraham R., Colonno R.J., and Lin P.F. J. Virol. 77 (2003) 10528-10536
16. Wang H.G., Williams R.E., and Lin P.F. Curr. Pharm. Des. 10 (2004) 1785-1793
17. Wang T., Zhang Z., Wallace O.B., Deshpande M., Fang H., Yang Z., Zadjura L.M., Tweedie D.L., Huang S., Zhao F., Ranadive S., Robinson B.S., Gong Y.F., Ricarrdi K., Spicer T.P., Deminie C., Rose R., Wang H.G., Blair W.S., Shi P.Y., Lin P.F., Colonno R.J., and Meanwell N.A. J. Med. Chem. 46 (2003) 4236-4239
18. Madani N., Perdigoto A.L., Srinivasan K., Cox J.M., Chruma J.J., LaLonde J., Head M., Smith III A.B., and Sodroski J.G. J. Virol. 78 (2004) 3742-3752
19. Schon A., Madani N., Klein J.C., Hubicki A., Ng D., Yang X., Smith III A.B., Sodroski J., and Freire E. Biochemistry 45 (2006) 10973-10980
20. Si Z., Madani N., Cox J.M., Chruma J.J., Klein J.C., Schon A., Phan N., Wang L., Biorn A.C., Cocklin S., Chaiken I., Freire E., Smith III A.B., and Sodroski J.G. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5036-5041
21. Stricher F., Martin L., Barthe P., Pogenberg V., Mechulam A., Menez A., Roumestand C., Veas F., Royer C., and Vita C. Biochem. J. 390 (2005) 29-39
22. Kong R., Tan J.J., Ma X.H., Chen W.Z., and Wang C.X. Biochim. Biophys. Acta 1764 (2006) 766-772
23. Lu R.J., Tucker J.A., Zinevitch T., Kirichenko O., Konoplev V., Kuznetsova S., Sviridov S., Pickens J., Tandel S., Brahmachary E., Yang Y., Wang J., Freel S., Fisher S., Sullivan A., Zhou J., Stanfield-Oakley S., Greenberg M., Bolognesi D., Bray B., Koszalka B., Jeffs P., Khasanov A., Ma Y.A., Jeffries C., Liu C., Proskurina T., Zhu T., Chucholowski A., Li R., and Sexton C. J. Med. Chem. 50 (2007) 6535-6544
24. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639-1662
25. Hawkins G.D., Cramer C.J., and Truhlar D.G. J. Phys. Chem. 100 (1996)
26. Tsui V., and Case D.A. Biopolymers 56 (2001) 275-291
27. Case D., Darden T., Cheatham T., Simmerling C., Wang J., Duke R., Luo R., Merz K., Pearlman D., Crowley M., Walker R., Zhang W., Wang B., Hayik S., Roitberg A., Seabra G., Wong K., Paesani F., Wu X., Brozell S., Tsui V., Gohlke H., Yang L., Tan C., Mongan J., Hornak V., Cui G., Beroza P., Mathews D., Schafmeister C., Ross W., and Kollman P. AMBER (2006), University of California, San Francisco
28. Humphrey W., Dalke A., and Schulten K. J. Mol. Graph. 14 (1996) 33-38
29. Hu Q.X., Barry A.P., Wang Z.X., Connolly S.M., Peiper S.C., and Greenberg M.L. J. Virol. 74 (2000) 11858-11872
30. Mink M., Mosier S.M., Janumpalli S., Davison D., Jin L., Melby T., Sista P., Erickson J., Lambert D., Stanfield-Oakley S.A., Salgo M., Cammack N., Matthews T., and Greenberg M.L. J. Virol. 79 (2005) 12447-12454
31. Klebe G., Abraham U., and Mietzner T. J. Med. Chem. 37 (1994) 4130-4146
32. Staahle L., and Wold S. J. Chemom. 1 (1987) 185-196
33. S. Wold, C. Albano, W.J. Dunn, U. Edlund, K. Esbenson, P. Geladi, S. Hellberg, W. Lindburg, M. Sjostrom. Chemometrics: Mathematics and Statistics in Chemistry, The Netherlands, Dordrecht, 1984.
34. Vong R., Geladi P., Wold S., and Esbensen K. J. Chemom. 2 (1988) 281-296
35. Xiang S.H., Kwong P.D., Gupta R., Rizzuto C.D., Casper D.J., Wyatt R., Wang L., Hendrickson W.A., Doyle M.L., and Sodroski J. J. Virol. 76 (2002) 9888-9899
36. Bohm M., Abraham U., and Mietzner T. J. Med. Chem. 37 (1994)
37. Cho S.J., and Tropsha A. J. Med. Chem. 38 (1995) 1060-1066
38. Bringmann G., and Rummey C. J. Chem. Inf. Comput. Sci. 43 (2003) 304-316
39. AMPAC, Semichem, Inc., PO Box 1649, Shawnee, KS 66222, 1992-2004.