Design, synthesis and biological evaluation of small molecule inhibitors of CD4-gp120 binding based on virtual screening

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 1, 2011, Pages 91-101

  Lalonde, Judith M ^a   Elban, Mark A ^b   Courter, Joel R ^b   Sugawara, Akihiro ^b   Soeta, Takahiro ^b   Madani, Navid ^c   Princiotto, Amy M ^c   Kwon, Young Do ^d   Kwong, Peter D ^d   Schön, Arne ^e   Freire, Ernesto ^e   Sodroski, Joseph ^c   Smith III, Amos B ^b  

^a BRYN MAWR COLLEGE   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c DANA FARBER CANCER INSTITUTE   (United States)

^d NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES   (United States)

^e JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

CD4; Docking; Entry inhibitor; gp120; HIV; Shape based similarity; Virtual screening

Indexed keywords

AMINE; ANTIVIRUS AGENT; CD4 ANTIGEN; GLYCOPROTEIN GP 120; SMALL MOLECULE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR DOCKING; NONHUMAN; PROTEIN INTERACTION; RECEIVER OPERATING CHARACTERISTIC; STRUCTURE ACTIVITY RELATION; VIRUS INFECTION; VIRUS INFECTIVITY;

ANTI-HIV AGENTS; ANTIGENS, CD4; DRUG DESIGN; HIV ENVELOPE PROTEIN GP120; MEMBRANE FUSION; MODELS, MOLECULAR; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 78650721466     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.11.049     Document Type: Article

References (45)

1. F. Barre-Sinoussi, J.C. Chermann, F. Rey, M.T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier Science 220 1983 868
2. R.C. Gallo, S.Z. Salahuddin, M. Popovic, G.M. Shearer, M. Kaplan, B.F. Haynes, T.J. Palker, R. Redfield, J. Oleske, and B. Safai Science 224 1984 500
3. M. Kowalski, J. Potz, L. Basiripour, T. Dorfman, W.C. Goh, E. Terwilliger, A. Dayton, C. Rosen, W. Haseltine, and J. Sodroski Science 237 1987 1351
4. A.G. Dalgleish, P.C. Beverley, P.R. Clapham, D.H. Crawford, M.F. Greaves, and R.A. Weiss Nature 312 1984 763
5. Q.J. Sattentau, and J.P. Moore J. Exp. Med. 174 1991 407
6. Q.J. Sattentau, J.P. Moore, F. Vignaux, F. Traincard, and P. Poignard J. Virol. 67 1993 7383
7. T. Dragic, V. Litwin, G.P. Allaway, S.R. Martin, Y. Huang, K.A. Nagashima, C. Cayanan, P.J. Maddon, R.A. Koup, J.P. Moore, and W.A. Paxton Nature 381 1996 667
8. Y. Feng, C.C. Broder, P.E. Kennedy, and E.A. Berger Science 272 1996 872
9. H. Deng, R. Liu, W. Ellmeier, S. Choe, D. Unutmaz, M. Burkhart, P. Di Marzio, S. Marmon, R.E. Sutton, C.M. Hill, C.B. Davis, S.C. Peiper, T.J. Schall, D.R. Littman, and N.R. Landau Nature 381 1996 661
10. R. Brasseur, B. Cornet, A. Burny, M. Vandenbranden, and J.M. Ruysschaert AIDS Res. Hum. Retroviruses 4 1988 83
11. R. Wyatt, and J. Sodroski Science 280 1998 1884
12. P.D. Kwong, R. Wyatt, J. Robinson, R.W. Sweet, J. Sodroski, and W.A. Hendrickson Nature 393 1998 648
13. R. Diskin, P.M. Marcovecchio, and P.J. Bjorkman Nat. Struct. Mol. Biol. 17 2010 608
14. U. Moebius, L.K. Clayton, S. Abraham, S.C. Harrison, and E.L. Reinherz J. Exp. Med. 176 1992 507
15. P.D. Kwong, R. Wyatt, S. Majeed, J. Robinson, R.W. Sweet, J. Sodroski, and W.A. Hendrickson Struct. Fold Des. 8 2000 8
16. D.G. Myszka, R.W. Sweet, P. Hensley, M. Brigham-Burke, P.D. Kwong, W.A. Hendrickson, R. Wyatt, J. Sodroski, and M.L. Doyle Proc. Natl. Acad. Sci. U.S.A. 97 2000 9026
17. S.A. Leavitt, A. Schon, J.C. Klein, U. Manjappara, I.M. Chaiken, and E. Freire Curr. Protein Pept. Sci. 5 2004 1
18. Q. Zhao, L. Ma, S. Jiang, H. Lu, S. Liu, Y. He, N. Strick, N. Neamati, and A.K. Debnath Virology 339 2005 213
19. N. Madani, A. Schon, A.M. Princiotto, J.M. Lalonde, J.R. Courter, T. Soeta, D. Ng, L. Wang, E.T. Brower, S.H. Xiang, Y.D. Kwon, C.C. Huang, R. Wyatt, P.D. Kwong, E. Freire, A.B. Smith 3rd, and J. Sodroski Structure 16 2008 1689
20. Y. Yamada, C. Ochiai, K. Yoshimura, T. Tanaka, N. Ohashi, T. Narumi, W. Nomura, S. Harada, S. Matsushita, and H. Tamamura Bioorg. Med. Chem. Lett. 20 2009 354
21. A. Schon, N. Madani, J.C. Klein, A. Hubicki, D. Ng, X. Yang, A.B. Smith 3rd, J. Sodroski, and F. Freire Biochemistry 45 2006 10973
22. H. Haim, Z. Si, N. Madani, L. Wang, J.R. Courter, A. Princiotto, A. Kassa, M. DeGrace, K. McGee-Estrada, M. Mefford, D. Gabuzda, A.B. Smith 3rd, and J. Sodroski PLoS Pathog. 5 2009 e1000360
23. K. Yoshimura, S. Harada, J. Shibata, M. Hatada, Y. Yamada, C. Ochiai, H. Tamamura, and S. Matsushita J. Virol. 84 2010 7558
24. T. Narumi, C. Ochiai, K. Yoshimura, S. Harada, T. Tanaka, W. Nomura, H. Arai, T. Ozaki, N. Ohashi, S. Matsushita, and H. Tamamura Bioorg. Med. Chem. Lett. 20 2010 5853 5858
25. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727
26. M.L. Verdonk, J.C. Cole, M.J. Hartshorn, C.W. Murray, and R.D. Taylor Proteins 52 2003 609
27. J.A. Grant, M.A. Gallardo, and B. Pickup J. Comput. Chem. 17 1996 1653
28. T.S. Rush 3rd, J.A. Grant, L. Mosyak, and A. Nicholls J. Med. Chem. 48 2005 1489
29. J.J. Irwin, and B.K. Shoichet J. Chem. Inf. Model. 45 2005 177
30. Zinc, http://zinc.docking.org/index.shtml, 2006.
31. Chembridge, San Diego, CA http://www.chembridge.com/.
32. MOE. Molecular Operating Environment, Chemical Computing Group Montreal Canada, http//www.chemcomp.com/, 2008.
33. T.A. Halgren J. Comput. Chem. 20 1999 720
34. T.A. Halgren J. Comput. Chem. 20 1999 740
35. S.C. Lovell, I.W. Davis, W.B. Arendall III, P.I.W. de Bakker, J.M. Word, M.G. Prisant, J.S. Richardson, and D.C. Richardson Proteins: Struct., Funct. Genet. 50 2003 437
36. J. Word, S. Lovell, J. Richardson, and D. Richardson J. Mol. Biol. 285 1999 1735
37. W.L. Jorgensen, D.S. Maxwell, and J. Tirado-Rives J. Am. Chem. Soc. 117 1996 11225
38. T.A. Halgren, R.B. Murphy, R.A. Friesner, H.S. Beard, L.L. Frye, W.T. Pollard, and J.L. Banks J. Med. Chem. 47 2004 1750
39. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, D.T. Mainz, M.P. Repasky, E.H. Knoll, M. Shelley, J.K. Perry, D.E. Shaw, P. Francis, and P.S. Shenkin J. Med. Chem. 47 2004 1739
40. ROCS, OpenEye Scientific Software, Inc 3600 Cerrillos Road, Suite 1107, Santa Fe, NM 87507, www.eyesopen.com, 2008.
41. J.E.J. Mills, and P.M. Dean J. Comput. Aided Mol. Des. 10 1996 607
42. T. Mirzabekov, N. Bannert, M. Farzan, W. Hofmann, P. Kolchinsky, L. Wu, R. Wyatt, and J. Sodroski J. Biol. Chem. 274 1999 28745
43. G.J. Babcock, T. Mirzabekov, W. Wojtowicz, and J. Sodroski J. Biol. Chem. 276 2001 38433
44. H.M. Rho, B. Poiesz, F.W. Ruscetti, and R.C. Gallo Virology 112 1981 355
45. Schön, A.; Madani, N.; Smith, A. B, 3rd; LaLonde, J. M; Freire, E. Chem. Biol. Drug Des. 2010, in press.