Time-resolved fluorescence anisotropy of HIV-1 protease inhibitor complexes correlates with inhibitory activity

Biochemistry

Volumn 37, Issue 9, 1998, Pages 2778-2786

  Kungl, A J ^a   Visser, N V ^b   Van Hoek, A ^b   Visser, A J W G ^b   Billich, A ^a   Schilk, A ^a,c   Gstach, H ^a   Auer, M ^a  

^a Novartis Forschungsinstitut ^*  (Austria)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c BOEHRINGER INGELHEIM RCV GMBH AND CO KG   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANOLAMINE; PROTEINASE; PROTEINASE INHIBITOR; STATIN; TRYPTOPHAN;

ANISOTROPY; ARTICLE; DISSOCIATION CONSTANT; ENZYME CONFORMATION; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; PROTEINASE INHIBITION; STRUCTURE ANALYSIS; VIRUS INHIBITION;

FLUORESCENCE POLARIZATION; HIV PROTEASE; HIV PROTEASE INHIBITORS; KINETICS; MODELS, MOLECULAR; PROTEIN CONFORMATION;

EID: 0032478295     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi971654w     Document Type: Article

References (48)

1. De Clercq, E. (1995) J. Med. Chem. 38, 2491-2517.
2. Mitsuya, H., Yarchoan, R., and Broder, S. (1990) Science 249, 1533-1544.
3. Gait, M. J., and Karn, J. (1995) Trends Biotechnol. 13, 430-438.
4. Collier, A. C., Coombs, R. W., Schoenfeld, D. A., Bassett, R. L., Timpone, J., Baruch, A., Jones, M., Facey, K., Whitacre, C., McAuliffe, V. J., Friedman, H. M., Merigan, T. C., Reichman, R. C., Hooper, C., and Corey, L. (1996) N. Engl. J. Med. 334, 1011-1017.
5. Wlodawer, A., and Erickson, J. W. (1993) Annu. Rev. Biochem. 62, 543-585.
6. Wlodawer, A., Miller, M., Jaskolski, M., Sathyanarayana, B. K., Baldwin, E., Wever, I. T., Selk, L. M., Clawson, L., Schneider, J., and Kent, S. B. H. (1989) Science 245, 616-621.
7. Appelt, K. (1993) Perspect. Drug Discovery Des. 1, 23-48.
8. Ringe, D. (1994) Methods Enzymol. 241, 157-177.
9. Gustchina, A., and Weber, I. T. (1990) FEBS Lett. 269, 269-272.
10. Umezawa, H., Aoyagi, T., Morishima, H., Matsuzaki, M., Hamada, M., and Takeuchi, T. (1970) J. Antibiot. 23, 259-262.
11. Debouck, C. (1992) Res. Hum. Retroviruses 8, 153-164.
12. Billich, A., Charpiot, B., Fricker, G., Gstach, H., Lehr, P., Peichl, P., Scholz, D., and Rosenwirth, B. (1994) Antiviral Res. 25, 215-233.
13. Miller, M., Schneider, J., Sathyanarayana, B. K., Toth, M. V., Marshall, G. R., Clawson, L., Selk, L., Kent, S. H. B., and Wlodawer, A. (1989) Science 246, 1149-1152.
14. Wonacott, A., Cooke, R., Hayes, F. R., Hann, M. M., Jhoti, H., McMeekin, P., Mistry, A., Murray-Rost, P., Singh, O. M., and Weir, M. P. (1993) J. Med. Chem. 36, 3113-3119.
15. 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.
16. Pearlman, D. A., and Murcko, M. A. (1996) J. Med. Chem. 39, 1651-1663.
17. Eftink, M. R. (1991) Methods Biochem. Anal. 35, 127-205.
18. Lakowicz, J. R. (1983) Principles of Fluorescence Spectroscopy. Plenum Press, New York/London.
19. Steiner, R. F. (1991) in Topics in Fluorescence Spectroscopy 2 (Lakowicz, J. R., Ed.) Plenum Press, New York/London.
20. Elofsson, A., Nilsson, L., and Rigler, R. (1990) Int. J. Pept. Protein Res. 36, 267-301.
21. Axelsen, P. H., Gratton, E., and Prendergast, F. G. (1991) Biochemistry 30, 1173-1179.
22. Jones, B. E., Beechem, J. M., and Matthews, C. R. (1995) Biochemistry 34, 1867-1877.
23. Seelmeier, S., Schmidt, H., Turk, V., and von der Helm, K. (1988) Proc. Natl. Acad. Sci. U.S.A. 85, 6612-6616.
24. Billich, A., Hammerschmid, F., and Winkler, G. (1990) Biol. Chem. Hoppe-Seyler 371, 265-272.
25. Richards, A., Phylip, L. H., Farmerie, W. G., Scarborough, P. E., Alvarez, A., Dunn, B. M., Hirel, P. H., Konvalinka, J., Strop, P., Pavlickova, L., Kostka, V., and Kay, J. (1990) J. Biol. Chem. 265, 7733-7736.
26. Scholz, D., Billich, A., Charpiot, B., Ettmayer, P., Lehr, P., Rosenwirth, B., Schreiner, E., and Gstach, H. (1994) J. Med. Chem. 37, 3079-3089.
27. Billich, A., Fricker, G., Müller, I., Donatsch, P., Ettmayer, P., Gstach, H., Lehr, P., Peichl, P., Scholz, D., and Rosenwirth, B. (1995) Antimicrob. Agents Chemother. 39, 1406-1413.
28. Lehr, P., Billich, A., Charpiot, B., Ettmayer, P., Scholz, D., Rosenwirth, B., and Gstach, H. (1996) J. Med. Chem. 39, 2060-2067.
29. Ettmayer, P., Billich, A., Hecht, P., Rosenwirth, B., and Gstach, H. (1996) J. Med. Chem. 39, 3291-3299.
30. 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.
31. Thompson, W. J., Fitzgerald, P. M. D., Holloway, M. K., Emini, E. A., Darke, P. L., McKeever, B. M., Schleif, W. A., Quintero, J. C., Zugay, J. A., Tucker, T. J., Schwering, J. E., Homnick, C. F., Nunberg, J., Springer, J. P., and Huff, J. R. (1992) J. Med. Chem. 35, 1685-1701.
32. Holmes, D. S., Clemens, I. R., Cobley, K. N., Humber, D. C., Kitchin, J., Orr, D. C., Patel, B., Paternoster, I. L., and Storer, R. (1993) Bioorg. Med. Chem. Lett. 3, 503-508.
33. O'Connor, D. V., and Phillips, D. (1984) Time-Correlated Single Photon Counting, Academic Press, London.
34. van Hoek, A., Vos, K., and Visser, A. J. W. G. (1987) IEEE J. Quantum Electron. QE-23, 1812-1820.
35. Visser, A. J. W. G., van Engelen, J., Visser, N. V., van Hoek, A., Hilhorst, R., and Freedman, R. B. (1994a) Biochim. Biophys. Acta 1204, 225-234.
36. Visser, N. V., Visser, A. J. W. G., Konc, T., Kroh, P., and van Hoek, A. (1994b) Proc. SPIE 2137, 618-626.
37. Livesey, A. K., and Brochon, J.-C. (1987) Biophys. J. 52, 693-706.
38. Bastiens, P. I. H., van Hoek, A., Benen, J. A. E., Brochon, J.-C., and Visser, A. J. W. G. (1992) Biophys. J. 63, 839-853.
39. Eftink, M. R., and Ghiron, C. A. (1976) Biochemistry 15, 672-680.
40. Chen, L. X.-Q., Engh, R. A., and Fleming, G. R. (1988) J. Phys. Chem. 92, 4811-4816.
41. Rayner, D. M., and Szabo, A. G. (1978) Can. J. Chem. 56, 743-745.
42. Ross, J. A., Schmidt, C. J., and Brand, L. (1981) Biochemistry 20, 4369-4377.
43. West, M. L., and Fairlie, D. P. (1995) Trends Pharmacol. Sci. 16, 67-74.
44. Royer, C. A., Taue, P., Herve, G., and Brochon, J.-C. (1987) Biochemistry 26, 6472-6478.
45. Harrison, R. W., and Weber, I. T. (1994) Protein Eng. 7, 1353-1363.
46. Wagner, G. (1996) Nat. Struct. Biol. 2, 255-257.
47. Nicholson, L. K., Yamazaki, T., Torchia, D. A., Grzesiek, S., Bax, A., 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, 274-280.
48. Scholz, D., Billich, A., Charpiot, B., Ettmayer, P., Lehr, P., Rosenwirth, B., Schreiner, E., and Gstach, H. (1994) J. Med. Chem. 37, 3079-3089.