Discovery of dual inhibitors targeting both HIV-1 capsid and human cyclophilin A to inhibit the assembly and uncoating of the viral capsid

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 8, 2009, Pages 3177-3188

  Li, Jiebo ^a   Tan, Zhiwu ^a   Tang, Shixing ^b   Hewlett, Indira ^b   Pang, Ruifang ^a   He, Meizi ^a   He, Shanshan ^a   Tian, Baohe ^a   Chen, Kan ^a   Yang, Ming ^a  

^a PEKING UNIVERSITY   (China)

^b CENTER FOR BIOLOGICS EVALUATION AND RESEARCH   (United States)

Author keywords

Assembly; Capsid; Cyclophilin A; Disassembly; Dual inhibitor; HIV 1

Indexed keywords

1 (2,4,5 TRICHLOROPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (3 BROMOPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (3 BROMOPHENYL) 3 [2 [2 (DIETHYLAMINO) 6 METHYL 5 NITROPYRIMIDIN 4 YLAMINO]ETHYL]THIOUREA; 1 (3 BROMOPHENYL) 3 [2 [2 (DIETHYLAMINO) 6 METHYLPYRIMIDIN 4 YLAMINO]ETHYL]THIOUREA; 1 (3 CHLORO 4 METHYLPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (3 CHLORO 4 METHYLPHENYL) 3 (4 METHYL 3 NITROPHENYL)THIOUREA; 1 (3 CHLORO 4 METHYLPHENYL) 3 [2 [2 (DIETHYLAMINO) 6 METHYL 5 NITROPYRIMIDIN 4 YLAMINO]ETHYLTHIOUREA; 1 (3 CHLOROPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (3 FLUOROPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL) 3 (2 TOLYL)THIOUREA; 1 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL) 3 (4 TOLYL)THIOUREA; 1 (3,5 DIFLUOROPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (4 CHLOROPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (4 FLUOROPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (4 METHOXYPHENYL) 3 (3 OXO 1,3 DIHYDROISOBENZOFURAN 5 YL)THIOUREA; 1 (4 METHOXYPHENYL) 3 (NAPHTHALEN 2 YL)THIOUREA; 4 (3 (3 CHLOROPHENYL)THIOUREIDO) N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 (3 (3 FLUOROPHENYL)THIOUREIDO) N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 (3 (4 CHLOROPHENYL)THIOUREIDO) N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 (3 (4 FLUOROPHENYL)THIOUREIDO) N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 [3 (3 BROMOPHENYL)THIOUREIDO] N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 [3 (3 CHLORO 4 METHYLPHENYL)THIOUREIDO] N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 [3 (4 CHLOROPHENYL)THIOUREIDO] N (4 METHOXYPHENYL)BENZENESULFONAMIDE; 4 [3 (4 METHOXYPHENYL)THIOUREIDO] N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; INDORAMIN; N (5 METHYLISOXAZOL 3 YL) 4 (3 PHENYLTHIOUREIDO)BENZENESULFONAMIDE; N (5 METHYLISOXAZOL 3 YL) 4 [3 (2 TOLYL)THIOUREIDO]BENZENESULFONAMIDE; N (5 METHYLISOXAZOL 3 YL) 4 [3 (4 TOLYL)THIOUREIDO]BENZENESULFONAMIDE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; NONHUMAN; PROTEIN ASSEMBLY; PROTEIN BINDING; SIMIAN IMMUNODEFICIENCY VIRUS; VIRUS ASSEMBLY; VIRUS CAPSID; VIRUS REPLICATION;

ANTI-HIV AGENTS; CAPSID; CAPSID PROTEINS; CYCLOPHILIN A; DRUG DESIGN; DRUG RESISTANCE, VIRAL; HIV-1; HUMANS; MODELS, MOLECULAR; VIRUS ASSEMBLY; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1; MIRIDAE; SIMIAN IMMUNODEFICIENCY VIRUS;

EID: 64049088223     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.02.051     Document Type: Article

References (28)

1. Coffin J.M. Science 267 (1995) 483
2. Rossmann M.G. Proc. Natl. Acad. Sci. 85 (1988) 4625
3. Popovic M., Tenner-Racz K., Pelser C., Stellbrink H., Lunzen J., Lewis G., Kalyanaraman V., Gallo C.R., and Racz P. Proc. Natl. Acad. Sci. 102 (2005) 14807
4. Stremlau M. Science 318 (2007) 1565
5. Ganser-Pornillos B.K., von Schwedler U.K., Stray K.M., Aiken C., and Sundquist W.I. J. Virol. 78 (2004) 2545
6. Ganser-Pornillos B.K., Cheng A., and Yeager M. Cell 131 (2007) 70
7. Sundquist W.I., and Hill P.C. Cell 131 (2007) 17
8. Ternois F., Sticht J., Duquerroy S., Krausslich H.G., and Rey F.A. Nat. Struct. Mol. Biol. 12 (2005) 678
9. Tang C., Loeliger E., Kinde I., Kyere S., Mayo K., Barklis E., Sun Y., Huang M., and Summers M.F. J. Mol. Biol. 327 (2003) 1013
10. Kelly B.N., Kyere S., Kinde I., Tang C., Howard R.B., Robinson H., Sundquist I.W., Summers F.M., and Hill P.C. J. Mol. Biol. 373 (2007) 355
11. Jean-Francois G., Julien V., Clément M., Guy S., Yea-Lih L., and Alain C. J. Med. Chem. 49 (2006) 900
12. Li J., Chen J., Gui C.S., Li Z., Yu Q., Xu Q., Zhang J., Liu H., Xu S., and Jiang H.L. Bioorg. Med. Chem. 14 (2006) 2209
13. Nisole S., Lynch C., Stoye P.J., and Yap W.M. Proc. Natl. Acad. Sci. 101 (2004) 13324
14. Lanman J., Sexton J., Sakalian M., and Prevelige P.E. J. Virol. 76 (2002) 6900
15. Luban J. Cell 87 (1996) 1157
16. Li J., Chen J., Zhang L., Wang F., Gui C., Zhang L., Qin Y., Xu Q., Liu H., Nan F., Shen J., Bai D., Chen K., Shen X., and Jiang H.L. Bioorg. Med. Chem. 14 (2006) 5527
17. Liu J., Chen C.M., and Walsh C.T. Biochemistry 30 (1991) 2306
18. Fischer G., Berger E., and Bang H. FEBS Lett. 2 (1989) 267
19. Kofron J.L., Kuzmic P., Kishore V., Colon-Bonilla E., and Rich H.D. Biochemistry 30 (1991) 6127
20. Thaddeus A.T., Victoria W.M., Heidi G.B., Michael L.M., and Thomas D.M. Biochem. Biophys. Res. Commun. 168 (1990) 264
21. Timothy M.J., Alan E., Rodolfo G., and Rebort C. J. Biol. Chem. 271 (1996) 7712
22. Daria J.H., Jeifrey C.H., Abigail L.W., and Emilio A.E. Nucleic Acids. Res. 22 (1994) 1121
23. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., and Ferrin T.E. J. Comput. Chem. 25 (2004) 1605
24. Gershon H., Grefig A., and Clarke D.D. J. Hetercycl. Chem. 24 (1987) 205
25. Soai K., Yokoyama S., and Mochida K. Synthesis 7 (1987) 647
26. Katritzky A.R., Ji F.B., Fan W.Q., Beretta P., and Bertoldi M. J. Hetercycl. Chem. 29 (1992) 1519
27. Hazuda J.D., Felock P., Witmer M., Wolfe A., Stillmock K., Grobler A.J., Espeseth A., Gabryelski L., Schleif W., Blau C., and Miller D.M. Science 287 (2000) 646
28. Kallen J., Spitzfaden C., Zurini M.M., Wider G., Widmer H., Wuthrich K., and Walknshaw M. Nature 353 (1991) 276