Structure-based thermodynamic analysis of HIV-1 protease inhibitors

Biochemistry

Volumn 36, Issue 22, 1997, Pages 6588-6596

  Bardi, Jason S ^a   Luque, Irene ^a,b   Freire, Ernesto ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 AMINO 2 METHYLPROPYL)IMIDAZOLE; A 74704; A 76889; A 76928; A 77003; A 78791; A 98881; AMPRENAVIR; CGP 53820; PROTEINASE INHIBITOR; SB 203238; SB 203386; SB 206343; U 100313; U 89360; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; ENZYME INHIBITION; ENZYME KINETICS; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL; THERMODYNAMICS; VIRUS MUTATION;

BINDING SITES; DRUG STABILITY; HIV PROTEASE; HIV PROTEASE INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTATION; PROTEIN BINDING; THERMODYNAMICS;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0030905238     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9701742     Document Type: Article

References (42)

1. Abdel-Meguid, S. S., Metcalf, B. W., Carr, T. J., Demarsh, P., DesJarlais, R. L., Fisher, S., Green, D. W., Ivanoff, L., Lambert, D. M., Murthy, K. H. M., Petteway, S. R., Jr., Pitts, W. J., Tomaszek, T. A., Jr., Winborne, E., Baoguang Zhao, B., Dreyer, G. B., & Meek, T. D. (1994) Biochemistry 33, 11671-11677.
2. Baldwin, E. T., Bhat, T. N., Liu, B., Pattabiraman, N., & Erickson, J. W. (1995) Nat. Struct. Biol. 2, 244-249.
3. Baldwin, R. L. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 8069-8072.
4. Cabani, S., Gianni, P., Mollica, V., & Lepori, L. (1981) J. Solution Chem. 10, 563-595.
5. 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., & Emini, E. A. (1995) Nature 374, 569-571.
6. D'Aquino, J. A., Gómez, J., Hilser, V. J., Lee, K. H., Amzel, L. M., & Freire, E. (1996) Proteins 25, 143-156.
7. Erickson, J. W., Neidhart, D. J., Van Drie, 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., & Knigge, M. (1990) Science 249, 527-529.
8. Fassler, A., Rosel, J., Grutter, M., Tintelnot, M., Alter, E., Bold, G., & Lang, M. (1993) Bioorg. Med. Chem. Lett. 3, 2817-2842.
9. García-Moreno, B. E. (1995) Methods Enzymol. 259, 512-538.
10. García-Moreno, B. E., Dwyer, J. J., Gittis, A. G., Lattman, E. E., Spencer, D. S., & Stites, W. E. (1997) Biophys. Chem. (in press).
11. Gomez, J., & Freire, E. (1995) J. Mol. Biol. 252, 337-350.
12. Gomez, J., Hilser, J. V., Xie, D., & Freire, E. (1995) Proteins: Struct., Funct., Genet. 22, 404-412.
13. Hilser, V. J., & Freire, E. (1996a) Proteins (in press).
14. Hilser, V. J., & Freire, E. (1996b) J. Mol. Biol. 262, 756-772.
15. Hilser, V. J., & Freire, E. (1996c) Biophys. Chem. (in press).
16. Hilser, V. J., Gomez, J., & Freire, E. (1996) Proteins 26, 123-133.
17. Ho, D. D., Toyoshima, T., Mo, H., Kempf, D. J., Norbeck, D., Chen, C., Wideburg, N. E., Burt, S. K., Erickson, J. W., & Singh, M. K. (1994) J. Virol. 68, 2016-2020.
18. Hoog, S. S., Zhao, B., Winbornel, E., Fisher, S., Green, D. W., DesJarlais, R. L., Newlander, K. A., Callahan, J. F., Moore, M. L., Huffman, W. F., & Abdel-Meguid, S. S. (1995) J. Med. Chem. 38, 3246-3252.
19. Hyland, L. J., Tomaszek, J. T. A., & Meek, T. D. (1991) Biochemistry 30, 8454-8463.
20. Janin, J. (1995) Proteins 21, 30-39.
21. 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. (1994) Proc. Natl. Acad. Sci. U.S.A. 91, 5597-5601.
22. Kauzmann, W. (1959) Adv. Protein Chem. 14, 1-63.
23. Kim, E. E., Baker, C. T., Dwyer, M. D., Murcko, M. A., Rao, B. G., Tung, R. D., & Navia, M. A. (1995) J. Am. Chem. Soc. 117, 1181-1182.
24. Lee, B., & Richards, F. M. (1971) J. Mol. Biol. 55, 379-400.
25. Lee, K. H., Xie, D., Freire, E., & Amzel, L. M. (1994) Proteins: Struct., Funct., Genet. 20, 68-84.
26. Lin, Y., Lin, X., Hong, L., Foundling, S., Heinrikson, R. L., Thaisrivongs, S., Leelamanit, W., Raterman, D., Shah, M., Dunn, B. D., & Tang, J. (1995) Biochemistry 34, 1143-1152.
27. Luque, I., Mayorga, O., & Freire, E. (1996) Biochemistry 35, 13681-13688.
28. Madhusoodan, V. H., Bhat, T. N., Kempf, D. J., Baldwin, E. T., Liu, B., Gulnik, S., Wideburg, N. E., Norbeck, D. W., Appelt, K., & Erickson, J. W. (1994) J. Am. Chem. Soc. 116, 847-855.
29. Murphy, K. P., & Freire, E. (1992) Adv. Protein Chem. 43, 313-361.
30. Murphy, K. P., Bhakuni, V., Xie, D., & Freire, E. (1992) J. Mol. Biol. 227, 293-306.
31. Murphy, K. P., Xie, D., Thompson, K., Amzel, L. M., & Freire, E. (1994) Proteins: Struct., Funct., Genet. 18, 63-67.
32. Roberts, N. A. (1995) AIDS 9, S27-S32.
33. Schellman, J. A. (1955a) C. R. Trav. Lab. Carlsberg, Ser. Chim. 29, 230-259.
34. Schellman, J. A. (1955b) C. R. Trav. Lab. Carlsberg, Ser. Chim. 29, 223-229.
35. Schinazi, R. F., Larder, B. A., & Mellors, J. W. (1996) Int. Antiviral News 4, 95-100.
36. Smith, R., Brereton, I. M., Chai, R. Y., & Kent, S. B. H. (1996) Nat. Struct. Biol. 3, 946-950.
37. Spinelli, S., Liu, Q. Z., Alzari, P. M., Hirel, P. H., & Poljak, R. J. (1991) Biochimie 73, 1391-1396.
38. Thaisrivongs, S., Watenpaugh, K. D., Howe, W. J., Timich, P. K., Dolak, L. A., Chong, K. T., Tomich, C. S., Tomasselli, A. G., Turner, S. R., Strohbach, J. W., Mulichak, A. M., Janakiraman, M. N., Moon, J. B., Lynn, J. C., Horng, M. M., Hinshaw, R. R., Curry, K. A., & Rothrock, D. J. (1995) J. Med. Chem. 38, 3624-3637.
39. Thompson, S. K., Murthy, K. H. M., Zhao, B., Winborne, E., Green, D. W., Fisher, S. M., DesJarlais, R. L., Tomaszek, T. A., Jr., Meek, T. D., Gleason, J. G., & Abdel Meguid, S. S. (1994) J. Med. Chem. 37, 3100-3107.
40. Tisdale, M. (1996) Int. Antiviral News 4, 38-40.
41. Wang, Y. X., Freedberg, D. I., Yamazaki, T., Wingfield, P. T., Stahl, S. J., Kaufman, J. D., Kiso, Y., & Torchia, D. A. (1996) Biochemistry 35, 9945-9950.
42. Wlodawer, A., & Erickson, J. W. (1993) Annu. Rev. Biochem. 62, 543-585.