Molecular recognition of cyclic urea HIV-1 protease inhibitors

Journal of Biological Chemistry

Volumn 273, Issue 20, 1998, Pages 12325-12331

  Ala, Paul J ^a   DeLoskey, Richard J ^a   Huston, Edward E ^a   Jadhav, Prabhakar K ^a   Lam, Patrick Y S ^a   Eyermann, Charles J ^a   Hodge, C Nicholas ^a   Schadt, Margaret C ^a   Lewandowski, Frank A ^a   Weber, Patricia C ^a   McCabe, Denise D ^a   Duke, Jodie L ^a   Chang, Chong Hwan ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,7 DIBENZYL 2,3,4,5,6,7 HEXAHYDRO 5,6 DIHYDROXY 1,3 BIS[4 (HYDROXYMETHYL)BENZYL] 2H 1,3 DIAZEPIN 2 ONE; MOZENAVIR; PROTEINASE INHIBITOR; SD 146; UNCLASSIFIED DRUG; XK 216; XK 263; XV 636;

ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL;

ANTI-HIV AGENTS; AZEPINES; HIV PROTEASE; HIV PROTEASE INHIBITORS; HIV-1; HYDROGEN BONDING; MOLECULAR CONFORMATION; UREA;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 15444345861     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.273.20.12325     Document Type: Article

References (35)

1. Henderson, L. E., Benveniste, R. E., Sowder, R., Copeland, T. D., Schultz, A. M., and Oroszlan, S. (1988) J. Virol. 62, 2587-2595
2. Loeb, D. D., Hutchison, C. A., III, Edgell, M. H., Farmerie, W. G., and Swanstrom, R. (1989) J. Virol. 63, 111-121
3. Fitzgerald, P. M. D., and Springer, J. P. (1991) Annu. Rev. Biophys. Biophys. Chem. 20, 299-320
4. Wlodawer, A., and Erickson, J. W. (1993) Annu. Rev. Biochem. 62, 543-585
5. Darke, P. L., and Huff, J. R. (1994) Adv. Pharmacol. 25, 399-454
6. Ho, D. D, Toyoshima, T., Mo, H., Kempf, D. J., Norbeck, D., Chen, C.-M., Wideburg, N. E., Burt, S. K., Erickson, J. W., and Singh, M. K (1994) J. Virol. 68, 2016-2020
7. Kaplan, A. H., Michael, S. F., Wehbie, R. S., Knigge, M. F., Paul, D. A., Everitt, L., Kempf, D. J., Norbeck, D. W., Erickson, J. W., and Swanstrom, R. (1994) Proc. Natl. Acad. Sci U. S. A. 91, 5597-5601
8. el-Farrash, M. A., Kuroda, M. J., Kitazaki, T., Masuda, T., Kato, K., Hatanaka, M., and Harada, S. (1994) J. Virol. 68, 233-239
9. Condra, J. H., Schleif, W. A., Blahy, O. M., Gabryelski, L. J., Graham, D. J., Quintero, J. C., Rhodes, A., Robbins, H. L., Roth, E., Shivaprakash, M., Titus, D., Yang, T., Teppler, H., Squires, K. E., Deutsch, P. J., and Emini, E. A. (1995) Nature 374, 569-571
10. Markowitz, M., Mo, H., Kempf, D. J., Norbeck, D. W., Bhat, T. N., Erickson, J. W., and Ho, D. D. (1995) J. Virol. 69, 701-706
11. Gulick, R. M., Mellors, J. W., Havlir, D., Eron, J. J., Gonzalez, C., McMahon, D., Richman, D. D., Valentine, F. T., Jonas, L., Meibohm, A., Emini, E. A., and Chodakewitz, J. A. (1997) N. Engl. J. Med. 337, 734-739
12. Erickson, J., Neidhart, D. J., VanDrie, J., Kempf, D. J., Wang, X. C., Norbeck, D. W., Plattner, J. J., Rittenhouse, J. W., Turon, M., Wideburg, N., Kohlbrenner, W. E., Simmer, R., Helfrich, R., Paul, D. A., and Knigge, M. (1990) Science 249, 527-533
13. Dreyer, G. B., Boehm, J. C., Chenera, B., DesJarlais, R. L., Hassell, A. M., Meek, T. D., Tomaszek, T. A., Jr., and Lewis, M. (1993) Biochemistry 32, 937-947
14. Lam, P. Y. S., Jadhav, P. K., Eyermann, C. J, Hodge, C. N., Ru, Y., Bacheler, L. T., Meek, J. L., Otto, M. J., Rayner, M. M., Wong, Y. N., Chang, C.-H., Weber, P. C., Jackson, D. A., Sharpe, T. R., and Erickson-Viitanen, S. (1994) Science 263, 380-384
15. De Lucca, G. V., Erickson-Viitanen, S., and Lam, P. Y. S. (1997) Drug Discovery Today 2, 6-18
16. Sham, H. L., Zhao, C., Stewart, K. D., Betebenner, D. A., Lin, S., Park, C. H., Kong, X. P., Rosenbrook, W., Jr, Herrin, T., Madigan, D., Vasavanonda, S., Lyons, N., Molla, A., Saldivar, A., Marsh, K. C., McDonald, E., Wideburg, N. E., Denissen, J. F., Robins, T., Kempf, D. J., Plattner, J. J., and Norbeck, D. W. (1996) J. Med. Chem. 39, 392-397
17. Hultén, J., Bonham, N. M., Nillroth, U., Hansson, T., Zuccarello, G., Bouzide, A., Åqvist, J., Classon, B., Danielson, H., Karlén, A., Kvarnström, I., Samuelsson, B., and Hallberg, A. (1997) J. Med. Chem. 40, 885-897
18. Bäckbro, K., S., Österlund, K., Atepo, J., Unge, T., Hultén, J., Bonham, N. M., Schaal, W., Karlén, A., and Hallberg, A. (1997) J. Med. Chem. 40, 898-902
19. Lam, P. Y. S., Ru, Y., Jadhav, P. K., Aldrich, P. E., DeLucca, G. V., Eyermann, C. J., Chang, C.-H., Emmett, G., Holler, E. R., Daneker, W. F., Li. L., Confalone, P. N., McHugh, R. J., Han, Q., Li, R., Markwalder, J. A., Seitz, S. P., Sharpe, T. R., Bacheler, R. T., Rayner, M. M., Klabe, R. M., Shum, L., Winslow, D. L., Kornhauser, D. M., Jackson, D. A., Erickson-Viitanen, S., and Hodge, C. N. (1996) J. Med. Chem. 39, 3514-3525
20. Lam, P. Y. S., Eyermann, C. J., Hodge, C. N., Jadhav, P. K., and Delucca, G. V. (March 11, 1997) U. S. Patent 5610294
21. Hodge, C. N., Aldrich, P., E., Bacheler, L. T., Chang, C.-H., Eyermann, C. J., Garber, S., Grubb, M., Jackson, D. A., Jadhav, P. K, Korant, B., Lam, P. Y. S., Maurin, M. B., Meek, J. L., Otto, M. J., Rayner, M. M., Reid, C., Sharpe, T. R., Shum, L., Winslow, D. L., and Erickson-Viitanen, S. (1996) Chem. Biol. 3, 301-314
22. Jadhav, P. K., Ala, P., Woerner, F. J., Chang, C.-H., Garber, S. S., Anton, E. D., and Bacheler, L. T. (1997) J. Med. Chem. 40, 181-191
23. Erickson-Viitanen, S., Klabe, R. M., Cawood, P. G., O'Neal, P. L., and Meek, J. L. (1994) Antiviral Chem. & Chemother. 38, 1628-1634
24. Korant, B., and Rizzo, C. (1992) Biol. Chem. Hoppe-Seyler 373, 517-521
25. Geng, X., and Chang, X. (1992) J. Chromatogr. 599, 185-194
26. Brünger, A. T., Kuriyan, J., and Karplus, M. (1987) Science 235, 458-460
27. Brünger, A. T. (1996) X-PLOR Version 3.851: A System for Crystallography and NMR, Yale University Press, New Haven, CT
28. Miller, M., Schneider, J., Sathyanarayana, B. K., Toth, M. V., Marshall, G. R., Clawson, L., Selk, L., Kent, S. B. H., and Wlodawer, A. (1989) Science 246, 1149-1152
29. Ala, P. J., Huston, E. E., Klabe, R. M., McCabe, D. D., Duke, J. L., Rizzo, C. J., Korant, B. D., DeLoskey, R. J., Lam, P. Y. S., Hodge, C. N., and Chang, C.-H. (1997) Biochemistry 36, 1573-1580
30. Nicholson, L. K., Yazamaki, T., Torchia, D. A., Grezesiek, S., Bax, S., Stahl, S. J., Kaufman, J. D., Wingfield, P. T., Lam, P. Y. S., Jadhav, P. K., Hodge, C. N., Domaille, P. J., and Chang, C.-H. (1995) Nat. Struct. Biol. 2, 274-279
31. Grzesiek, S., Bax, A., Nicholson, L. K., Yamazaki, T., Wingfield, P., Stahl, S. J., Eyermann, C. J., Torchia, D. A., Hodge, C. N., Lam, P. Y. S., Jadhav, P. K., and Chang, C.-H. (1994) J. Am. Chem. Soc. 116, 1581-1582
32. Roberts, N. A., Martin, J. A., Kinchington, D., Broadhurst, A. V., Craig, J . C., Duncan, I. B., Galpin, S. A., Handa, B. K., Kay, J., Kröhn, A., Lambert, R. W., Merrett, J. H., Mills, J. S., Parkes, K. E. B., Redshaw, S., Ritchie, A. J., Taylor, D. L., Thomas, G. J., and Machin, P. J. (1990) Science 248, 358-361
33. Chen, Z., Li, Y., Chen, E., Hall, D. L., Darke, P. L., Culberson, C., Shafe, J. A., and Kuo, L. C. (1994) J. Biol. Chem. 269, 26344-26348
34. Kempf, D. J., Marsh, K. C., Denissen, J. F., McDonald, E., Vasavanonda, S., Flentge, C. A., Green, B. E., Fino, L., Park, C. H., Kong, X. P., Wideburg, N. E., Saldivar, A., Ruiz, L., Kati, W. M., Sham, H. L., Robins, T., Stewart, K. D., Hsu, A., Plattner, J. J., Leonard, J. M., and Norbeck, D. W. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 2484-2488
35. Loeb, D. D., Swanstrom, R., Everitt, L., Manchester, M., Stamper, S. E., and Hutchison, C. A., III (1989) Nature 340, 397-400