Peptidyl epoxides: Novel selective inactivators of cysteine proteases

Journal of the American Chemical Society

Volumn 118, Issue 15, 1996, Pages 3591-3596

  Albeck, Amnon ^a   Fluss, Shulamit ^a   Persky, Rachel ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLOXYCARBONYLPHENYLALANYL O BENZYLTHREONINE EPOXIDE; BENZYLOXYCARBONYLPHENYLALANYLALANINE EPOXIDE; CATHEPSIN B; CHYMOTRYPSIN; CLOSTRIPAIN; CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; ELASTASE; ENZYME INHIBITOR; EPOXIDE; PAPAIN; PEPTIDE DERIVATIVE; SERINE PROTEINASE; SUBTILISIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0029984218     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954261y     Document Type: Article

References (59)

1. Abbreviations: amino acids are written in their three-letter codes; Bn, benzyl; Cbz, benzyloxycarbonyl; BAEE, Nα-benzoyl-L-arginine ethyl ester; BTEE, N-benzoyl-L-tyrosine ethyl ester; Succ-AAA-pNA, N-succinyl-Ala-Ala-Ala p-nitroanilide; Succ-AAPF-pNA, N-succinyl-Ala-Ala-Pro-Phe p-nitroanilide; ONp, o-nitrophenol; TFA, trifluoroacetic acid; DIBAL, diisobutylaluminum hydride; mCPBA, 3-(chloroperoxy)benzoic acid, Tris, tris(hydroxymethyl)aminomethane.
2. Proteinase Inhibitors; Research Monographs in Cell and Tissue Physiology, Barrett, A. J., Salvesen, G. Eds.; Elsevier: Amsterdam, 1986, Vol. 12, Chapters 7-20, pp 301-612.
3. (a) Rich, D. H. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. C., Taylor, J. B., Eds., Pergamon Press: Oxford, 1990; Vol. 2, pp 391-441.
4. (b) Fischer, G. Nat. Prod. Rep. 1988, 465-495.
5. (c) Powers, J C.; Harper, J W. In Proteinase Inhibitors; Research Monographs in Cell and Tissue Physiology; Barrett, A. J., Salvesen, G., Eds , Elsevier, Amsterdam, 1986; Vol 12, pp 55-152.
6. (a) Markland, F. S.; Shaw, E.; Smith, E. L. Proc. Nat. Acad. Sci U.S.A. 1968, 61, 1440-1447.
7. (b) Schoellmann, G.; Shaw, E. Biochemistry 1963, 2, 252-255.
8. (a) Brady, K.; Liang, T.-C ; Abeles, R H. Biochemistry 1989, 28, 9066-9070.
9. (b) Liang, T.-C , Abeles, R. H Biochemistry 1987, 26, 7603-7608.
10. (a) Kaplan, A. P., Bartlett, P. A. Biochemistry 1991, 30, 8165-8170.
11. (b) Bartlett, P. A ; Hanson, J. E.; Giannousis, P P. J. Org. Chem. 1990, 55, 6268-6274
12. (c) Hanson, J. E.; Kaplan, A. P.; Bartlett, P. A Biochemistry 1989, 28, 6294-6305
13. (a) Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H Freeman and Co : New York, 1985; pp 405-426.
14. (b) Walsh, C. Enzymatic Reaction Mechanisms. W. H. Freeman and Co. New York, 1979; pp 53-107
15. Arad, D.; Langride, R.; Kollman, P. A. J. Am. Chem. Soc. 1990, 112, 491-502.
16. Rich, D. H. In Proteinase Inhibitors; Research Monographs in Cell and Tissue Physiology. Barrett, A. J., Salvesen, G., Eds ; Elsevier: Amsterdam, 1986; Vol. 12, pp 153-178.
17. Pocker, Y , Ronald, B. P., Anderson, K. W J. Am. Chem. Soc. 1988, 110, 6492-6497.
18. Giordano, C.; Gallina, C.; Consalvi, V., Scandurra, R. Eur. J. Med. Chem 1990, 25, 479-487.
19. (a) Moore, M. L.; Fakhoury, S. A.; Bryan, W. M.; Bryan, H. G.; Tomaszek, T. A., Jr.; Grant, S. K.; Meek, T. D.; Huffman, W. F. In Peptides, Chemistry and Biology; Proceedings of the American Peptide Symposium, 12th: Smith, J. A.; Rivier, J. E. Eds.; ESCOM: Leiden, 1992; pp 781-782.
20. (b) Grant, S. K., Moore, M. L.; Fakhoury, S A.; Tomaszek, T. A., Jr.; Meek, T. D. Bioorg. Med. Chem. Lett. 1992, 2, 1441-1445.
21. (c) Johnson, R. L. In Peptides: Structure and Function; Proceedings of the American Peptide Symposium, 8th; Hruby, V. J., Rich, D. H. Eds.; Pierce Chem. Co.: Rockford, IL, 1983; pp 587-590.
22. Kim, D. H.; & Kim, K B. J. Am. Chem. Soc. 1991, 113, 3200-3202.
23. Albeck, A ; Persky, R ; Kliper, S. Bioorg. Med. Chem. Lett. 1995, 5, 1767-1772.
24. Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L., Yi, N. J. Org. Chem 1987, 52, 1487-1492
25. (a) Romeo, S.; Rich, D. H. Tetrahedron Lett. 1994, 35, 4939-4942.
26. (b) Romeo, S ; Rich, D. H. Tetrahedron Lett. 1993, 34, 7187-7190.
27. (c) Rich, D. H.; Sun, C.-Q.; Vara Prasad, J. V. N., Pathiasseril, A.; Toth, M. V , Marshall, G. R., Clare, M., Mueller, R A., Hauseman, K. J. Med. Chem. 1991, 34, 1222-1225.
28. Albeck, A., Persky, R. J. Org Chem. 1994, 59, 653-657.
29. Albeck, A.; Persky, R. Tetrahedron 1994, 50, 6333-6346.
30. (a) Powers, J C ; Lively, M. O ; Tippet, J T. Biochim. Biophys. Acta 1977, 480, 246-261.
31. (b) Powers, J. C. In Chemistry and Biology of Amino Acids, Peptides and Proteins: Weinstein, B., Ed., Marcel Dekker: New York, 1977; Vol. 4, pp 66-178.
32. (a) Delbaere, T. J.; Braver, G. D. J. Mol. Biol. 1987, 183, 89-103.
33. (b) Hassall, C. H.; Johnson, W. H.; Kennedy, A. J.; Roberts, N. A FEBS Lett. 1985, 183, 201-205.
34. (c) Galpin, I. J.; Wilby, A. H., Place, G. A.; Baynon, R. J. Int. J. Peptide Protein Res. 1984, 23, 477-486.
35. (d) Thompson, R. C. Biochemistry 1973, 12, 47-51.
36. (a) Stein, R. L.; Strimpler, A. M., Edwards, P D ; Lewis, J. J.; Mauger, R. S., Schwartz, J. A.; Stein, M. M., Trainor, D A , Wildonger, R A.; Zottola, M. A. Biochemistry 1987, 26, 2682-2689.
37. (b) Dunlap, R. P.; Stone, P J.; Abeles, R. H. Biochem. Biophys. Res. Commun. 1987, 145, 509-513
38. (c) Imperiali, B ; Abeles, R. H. Biochemistry 1986, 25, 3760-3767
39. Kettner, C. A., Shenvi, A. B. J. Biol. Chem. 1984, 259, 15106-15114
40. Kitz, R.; Wilson, I. B. J. Biol. Chem 1962, 237, 3245-3249.
41. The P and P′ for substrates and S and S′ for enzyme subsites terminology is used See Schechter. I . Berger. A Biochem Biophys. Res. Commun 1967, 27, 157-162
42. Berger, A.; Schechter, I. Philos. Trans. R. Soc. London 1970, B257, 249-264.
43. (a) Rauber, P.; Angliker, H.; Walker, B.; Shaw, E. Biochem. J. 1986, 239, 633-640.
44. (b) Shaw, E.; Wikstrom, P.; Ruscica, J Arch. Biochem. Biophys. 1983, 222, 424-429.
45. (c) Green, G. D. J.; Shaw, E. J. Biol. Chem. 1981, 256, 1923-1928.
46. (d) Leary, R.; Larsen, D.; Watanabe, H.; Shaw, E Biochemistry 1977, 16, 5857-5861.
47. (e) Roffman, L. S. PhD. Thesis, New York University, 1974, Order no. 74-30,038.
48. Barrett, A. J., Kirschke, H. Methods Enzymol. 1981, 80, 535-561.
49. (a) Polgar, L.; Halasz, P Biochem. J. 1982, 207, 1-10.
50. (b) Johnson, F. A.; Lewis, S. D.; Shafer, J. A. Biochemistry 1981, 20, 44-48.
51. (c) Lewis, S. D.; Johnson, F A.; Shafer, J. A. Biochemistry 1981, 20, 48-51.
52. (a) Yamamoto, D.; Matsumoto, K.; Ohishi, H.; Ishida, T.; Inoue, M., Kitamura, K.; Mizuno, H. J. Biol. Chem. 1991, 266, 14771-14777
53. (b) Varughese, K. I.; Ahmed, F. R.; Carey, P. R., Hasnain, S.; Huber, C P.; Storer, A. C. Biochemistry 1989, 28, 1330-1332.
54. Krebs, K. G.; Heusser, D.; Wimmer, H. In Thin Layer Chromatography, 2nd ed.; Stahl, E., Ed.; Springer-Verlag: New York, 1969; p 862.
55. Still, W. C.; Kahn, M.; Mitra, A. J. Ogr. Chem. 1978, 43, 2923-2925.
56. Hummel, B. C. W. Can. J. Biochem. Physiol. 1959, 37, 1393-1399.
57. Del Mar, E. G.; Langman, C.; Brodrick, J. W.; Geckas, M. C. Anal. Biochem. 1979, 99, 316-320.
58. Bieth, J.; Spiess, B.; Wermuth, C. G. Biochem. Med. 1974, 11, 350-357.
59. Gilles, A.; Imhoff, J.; Keil, B. J. Biol. Chem. 1979, 254, 1462-1468.