Counteracting HIV-1 protease drug resistance: Structural analysis of mutant proteases complexed with XV638 and SD146, cyclic urea amides with broad specificities

Biochemistry

Volumn 37, Issue 43, 1998, Pages 15042-15049

  Ala, Paul J ^a,b   Huston, Edward E ^a   Klabe, Ronald M ^a   Jadhav, Prabhakar K ^a   Lam, Patrick Y S ^a   Chang, Chong Hwan ^a  

^a DUPONT COMPANY   (United States)

^b Scriptgen Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPRENAVIR; ANTIVIRUS AGENT; INDINAVIR; NELFINAVIR; PROTEINASE INHIBITOR; RITONAVIR; SAQUINAVIR; SD 146; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFICACY; DRUG RESISTANCE; ENZYME ACTIVE SITE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; PRIORITY JOURNAL; PROTEIN CONFORMATION; STRUCTURE ANALYSIS;

AMINO ACID SUBSTITUTION; BINDING SITES; DRUG RESISTANCE, MICROBIAL; HIV PROTEASE; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; SUBSTRATE SPECIFICITY; UREA;

EID: 0032573197     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi980386e     Document Type: Article

References (41)

1. Robins, T., and Plattner, J. (1993) J. Acquired Immune Defic. Syndr. 6, 162-170.
2. Kohl, N. E., Emini, E. A., Schleif, W. A., Davis, L. J., Heimbach, J. C., Dixon, R. A. F., Scolnick, E. M., and Sigal, I. S. (1988) Proc. Natl. Acad. Sci. U.S.A. 85, 4686-4690.
3. Peng, C., Ho, B. K., Chang, T. W., and Chang, N. T. (1989) J. Virol. 63, 2550-2556.
4. Wlodawer, A., and Erickson, J. W. (1993) Annu. Rev. Biochem. 62, 543-585.
5. De Lucca, G., Erickson-Viitanen, S., and Lam, P. Y. S. (1997) Drug Discovery Today 2, 6-18.
6. 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.
7. Dorsey, B. D., Levin, R. B., McDaniel, S. L., Vacca, J. P., Guare, J. P., Darke, P. L., Zugay, J. A., Emini, E. A., Schleif, W. A., Quintero, J. C., Lin, J. H., Chen, I.-W., Holloway, M. K., Fitzgerald, P. M. D., Axel, M. G., Ostovic, D., Anderson, P. S., and Huff, J. R. (1994) J. Med. Chem. 37, 3443-3451.
8. 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.
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. Molla, A., Korneyeva, M., Gao, Q., Vasavanonda, S., Schipper, P. J., Mo, H.-M., Markowitz, M., Chernyavskiy, T., Niu, P., Lyons, N., Hsu, A., Granneman, G. R., Ho, D. D., Boucher, C. A. B., Leonard, J. M., Norbeck, D. W., and Kempf, D. J. (1996) Nat. Med. 2, 760-766.
11. Patick, A. K., Mo, H., Markowitz, M., Appelt, K., Wu, B., Musick, L., Kalish, V., Kaldor, S., Reich, S., Ho, D., and Webber, S. (1996) Antimicrob. Agents Chemother. 40, 292-297.
12. Ives, K. J., Jacobsen, H., Galpin, S. A., Garaev, M. M., Dorrell, L., Mous, J., Bragman, K., and Weber, J. N. (1997) J. Antimicrob. Chemother. 39, 771-779.
13. Wong, J. K., Hezareh, M., Günthard, H. F., Havlir, D. V., Ignacio, C. C., Spina, C. A., and Richman, D. D. (1997) Science 278, 1291-1295.
14. Mellors, J. W., Larder, B. A., and Schinazi, R. F. (1995) International Antiviral News 3, 8-13.
15. 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.
16. Baldwin, E. T., Bhat, T. N., Liu, B., Pattabiraman, N., and Erickson, J. W. (1995) Nat. Struct. Biol. 2, 244-249.
17. Hong, L., Treharne, A., Hartsuck, J. A., Foundling, S., and Tang, J. (1996) Biochemistry 35, 10627-10633.
18. Kervinen, J., Thanki, N., Zdanov, A., Tino, J., Barrish, J., Lin, P. F., Colonno, R., Riccardi, K., Samanta, H., and Wlodawer, A. (1996) Protein Pept. Lett. 3, 399-406.
19. 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.
20. Gulnik, S. V., Suvorov, L. I., Liu, B., Yu, B., Anderson, B., Mitsuya, H., and Erickson, J. W. (1995) Biochemistry 34, 9282-9287.
21. Klabe, R. M., Bacheler, L. T., Ala, P. J., Erickson-Viitanen, S., and Meek, J. L. (1998) Biochemistry 37, 8735-8742.
22. 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.
23. 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.
24. King, R. W., Garber, S., Winslow, D. L., Reid, C., Bacheler, L. T., Anton, E., and Otto, M. J. (1995) Antiviral Chem. Chemother. 6, 80-88.
25. 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.
26. Ala, P. J., DeLoskey, R. J., Huston, E. E., Jadhav, P. K., Lam, P. Y. S., Eyermann, C. J., Hodge, C. N., Schadt, M. C., Lewandowski, F. A., Weber, P. C., McCabe, D. D., Duke, J. L., and Chang, C.-H. (1998) J. Biol. Chem. 273, 12325-12331.
27. Geng, X., and Chang, X. (1992) J. Chromatogr. 599, 185-194.
28. 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.
29. Brünger, A. T., Kuriyan, J., and Karplus, M. (1987) Science 235, 458-460.
30. Erickson-Viitanen, S., Klabe, R. M., Cawood, P. G., O'Neal, P. L., and Meek, J. L. (1994) Antiviral Chem. Chemother. 38, 1628-1634.
31. Brünger, A. T. (1996) X-PLOR Version 3.851: A system for crystallography and NMR, Yale University Press, New Haven, CT.
32. Williams, K. J., and Loeb, L. A. (1992) Curr. Top. Microbiol. Immunol. 176, 165-180.
33. Wei, X., Ghosh, S. K., Taylor, M. E., Johnson, V. A., Emini, E. A., Deutsch, P., Lifson, J. D., Bonhoeffer, S., Nowak, M. A., Hahn, B. H., Saag, M. S., and Shaw, G. M. (1995) Nature 373, 117-122.
34. Pazhanisamy, S., Stuver, C. M., Cullinan, A. B., Margolin, N., Rao, B. G., and Livingston, D. J. (1996) J. Biol. Chem. 271, 17979-17985.
35. Schock, H. B., Garsky, V. M., and Kuo, L. C. (1996) J. Biol. Chem. 271, 31957-31963.
36. 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.
37. Furfine, E. S., D'Souza, E., Ingold, K. J., Leban, J. J., Spector, T., and Porter, D. J. T. (1992) Biochemistry 31, 7886-7891.
38. Ponder, J. W., and Richards, F. M. (1987) J. Mol. Biol. 193, 775-791.
39. Jacobsen, H., Yasargil, K., Winslow, D. L., Craig, J. C., Kröhn, A., Duncan, I. B., and Mous, J. (1995) Virology 206, 527-534.
40. 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.
41. Partaledis, J. A., Yamaguchi, K., Tisdale, M., Blair, E. E., Falcione, C., Maschera, B., Myers, R. E., Pazhanisamy, S., Futer, O., Cullinan, A. B., Stuver, C. M., Byrn, R. A., and Livingston, D. J. (1995) J. Virol. 69, 5228-5235.