Substrate-based cyclic peptidomimetics of Phe-Ile-Val that inhibit HIV-1 protease using a novel enzyme-binding mode

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3375-3379

  March, Darren R ^a   Abbenante, Giovanni ^a   Bergman, Douglas A ^a   Brinkworth, Ross I ^a   Wickramasinghe, Wasantha ^a   Begun, Jake ^a   Martin, Jennifer L ^a   Fairlie, David P ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CYCLOPEPTIDE; PROTEINASE INHIBITOR; PSEUDOPEPTIDE;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; ENZYME BINDING; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; X RAY ANALYSIS;

EID: 0029926111     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953790z     Document Type: Article

References (35)

1. (a) Blundell, T. L ; Lapatto, R., Wilderspin, A F.; Hemmings, A. M.; Hobart, P. M.; Danley, D E ; Whittle, P. J. TIBS 1990, 15, 425-430.
2. (b) Tomaselli, A. G., Howe, W. J.; Sawyer, T. K., Wlodawer, A ; Heinrikson, R. L. Chimu aoggi 1992, 6-27
3. (c) Wlodawer, A , Erickson, J W Ann. Rev. Biochem 1993, 62, 543-585 and references therein.
4. (d) Darke, P. L.; Huff, J. R. Adv Pharmacol 1994 25, 399-454
5. (e) West, M. L.; Fairlie, D P Trends Pharmacol. Sci. 1995, 16, 67-75
6. (a) Kohl, N E., Emini E A Schleif, W A , Davis L J.; Heimbach, J C , Dixon, R A F., Scolnick, E. M., Sigal, I S Proc Natl. Acad. Sci. U S A. 1988, 85, 4686-4690.
7. (b) Lambert, D M , Petteway, S R , Jr., McDanal, C. E., Hart, T K ; Leary, J J , Dreyer, G B , Meek, T D., Bugelski, P. J , Bolognesi, D. P , Metcalf, B. W , Matthews, T J Antimicrob. Agents Chemother 1992, 36, 982-988
8. Swain, A , Miller, M M , Green, J , Rich, D H ; Schneider, J., Kent, S. B. H , Wlodawer, A Proc. Natl Acad. Sci U S.A 1990, 87, 8805-8809
9. Bisacchi, G. S., Ahmad, S., Alam, M.; Ashfaq, A.; Barrish, J.; Cheng, P T. W ; Greytok, J ; Hermsmeter, M , Lin, P.-F.; Merchant, Z.; Skoog, M ; Spergel, S.; Zahler, R Bioorg Med Chem Lett. 1995, 5, 459-464.
10. (a) Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676-678.
11. (b) Rich, D. H.; Sun, C.-Q.; Prasad, J. V. N. V.; Pathiasseril, A.; Toth, M V , Marshall, G. R.; Clare, M.; Mueller, R. A.; Houseman, K. J. Med. Chem 1991, 34, 1222-1225.
12. (a) Schneider, J.; Kent, S. B. H. Cell 1988, 54, 363-8. Except that Aba replaces the Cys residues in the SF2 isolate as footnoted in:
13. (b) Wlodawer, A.; Miller, M.; Jaskólski, M.; Sathyanarayana, B. K.; Baldwin, E.; Weber, I. T.; Selk, L. M., Clawson, L.; Schneider, J.; Kent, S B. H. Science 1989, 245, 616-621 To minimize autocatalytic degradation two mutations (Q7K and L33I) were made for X-ray work.
14. (a) Toth, M.; Marshall, G. R Int. J. Pept. Protein Res. 1990, 36, 544-550.
15. (b) Bergman, D. A.; Alewood, D.; Alewood, P. F., Andrews, J. L.; Brinkworth, R. I.; Engelbretsen, D. R.; Kent, S. B H. Lett. Pept. Sci. 1995, 2, 99-107.
16. 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.; Erickson-Viitanen, S. Science 1994, 263, 380-384.
17. Kim, E. E.; Baker, C T.; Dwyer, M. D.; Murcko, M. A.; Rao, B. G.; Tung, R. D.; Navia, M. A. J. Am. Chem. Soc. 1995, 117, 1181-1182.
18. 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., Krohn, A.; Lambert, R. W.; Merret, J H.; Mills, J S , Parkes, K. E. B., Redshaw, S.; Ritchie, A. J.; Taylor, D. L., Thomas, G. J.; Machin, P J. Science 1990, 248, 358-361.
19. See partial review in: Fairlie, D. P., Abbenante, G., March, D. R. Curr Med. Chem. 1995, 2, 672-705.
20. (a) Abbenante, G.; March, D. R.; Bergman, D. A.; Hunt, P A ; Garnham, B., Dancer, R J.; Martin, J L., Fairlie, D. P J Am. Chem. Soc. 1995, 117, 10220-10226.
21. (b) Podlogar, B. L , Farr, R. A., Friedrich, D.; Tarnus, C., Huber, E. W., Cregge, R. J., Schirlin, D. J. Med. Chem. 1994, 37, 3684-3692.
22. (c) Smith, R A.; Coles, P. J.; Chen, J. J., Robinson, V. J., Macdonald, I. D., Carriere, J.; Krantz, A Bioorg Med. Chem. Lett. 1994, 4, 2217-2222.
23. 50 110 nM) under the same conditions.
24. PALLAS pKalc and PrologP available from Compudrug Chemistry Ltd. Hungary
25. 3 solution and extracted with ethyl acetate
26. Kocienski, P. J.; Cernigliaro, G., Feldstein, G. J. Org. Chem. 1977, 42, 353-355.
27. 12a
28. 12a
29. Ghosh, A. K.; Duong, T. T.; McKee, S. P.; Thompson, W. J. Tetrahedron Lett. 1992, 33, 2781-2784.
30. Quinaldyl-(S)-valine was synthesized by the BOP coupling of quinoline-2-carboxylic acid with valine methyl ester-HCl followed by de-esterification with NaOH.
31. Brünger, A. T. X-PLOR (Version 3.1) Manual. The Howard Hughes Medical Institute and Department of Molecular Biophysics and Biochemistry, Yale University, CT 06511, 1992.
32. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Acta Crystallogr., Sect. A 1991, 47, 110-119.
33. (a) Biosym Technologies Inc., San Diego,
34. (b) Dauber-Osguthorpe, P.; Roberts, V A.; Osguthorpe, D. J.; Wolff, J.; Genest, M.; Hageler, A. T Proteins 1988, 4, 31-47.
35. (c) Chen, X.; Tropsha, A. J. Med. Chem. 1995, 38, 42-48.