Synthesis and kinetic studies of diphenyl 1-(N- peptidylamino)alkanephosphonate esters and their biotinylated derivatives as inhibitors of serine proteases and probes for lymphocyte granzymes

Archives of Biochemistry and Biophysics

Volumn 344, Issue 2, 1997, Pages 271-280

  Abuelyaman, Ahmed S ^a   Jackson, Delwin S ^a   Hudig, Dorothy ^b   Woodard, Susan L ^b   Powers, James C ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF NEVADA SCHOOL OF MEDICINE   (United States)

Author keywords

Chymase; Chymotrypsin; Cytolysis; Elastase; Granzymes; Lymphocyte serine proteases; Phosphonate inhibitors

Indexed keywords

CHYMASE; CHYMOTRYPSIN; ELASTASE; GRANZYME A; PHOSPHONIC ACID DERIVATIVE; SERINE PROTEINASE;

ARTICLE; CATTLE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME SYNTHESIS; LYMPHOCYTE; PRIORITY JOURNAL; PROTEIN SYNTHESIS;

BOS TAURUS; BOVINAE; SUIDAE;

EID: 0031571612     PISSN: 00039861     EISSN: None     Source Type: Journal    
DOI: 10.1006/abbi.1997.0231     Document Type: Article

References (41)

1. Neurath H. Science. 224:1984;350-357.
2. Powers J. C., Harper J. W. Proteinase Inhibitors. 1986;Elsevier, Amsterdam. p. 55-152.
3. Rawlings N. D., Barrett A. J. Biochem. J. 290:1993;205-218.
4. Tschopp J., Jongeneel C. V. Biochemistry. 27:1988;2641-2646.
5. Hudig D., Ewoldt G. R., Woodard S. L. Curr. Opin. Immunol. 5:1993;90-96.
6. Odake S., Kam C.-M., Narasimhan L., Poe M., Blake J. T., Krahenbuh O., Tschopp J., Powers J. C. Biochemistry. 30:1991;2217-2227.
7. Smyth M. J., Wiltrout T., Trapani J. A., Ottaway K. S., Sowder R., Henderson L. E., Kam C.-M., Powers J. C., Young H. A., Sayers T. J. J. Biol. Chem. 267:1992;24418-24425.
8. Smyth M. J., Sayers T. J., Wiltrout T., Powers J. C., Trapani J. A. J. Immunol. 151:1993;6195-6205.
9. Baker E., Sutherland G. R., Smyth M. J. Immunogenetics. 39:1993;294-295.
10. Baker E., Sayers T. J., Sutherland G. R., Smyth M. J. Immunogenetics. 40:1994;235-237.
11. Heusel J. W., Hanson R. D., Silverman G. A., Ley T. J. J. Biol. Chem. 266:1991;6152-6158.
12. Hudig D., Haverty T., Fulcher C., Redelman D., Mendelsohn J. J. Immunol. 126:1981;1569-1574.
13. Ewoldt G. R., Winkler U., Powers J. C., Hudig D. Mol. Immun. 29:1992;713-721.
14. Hudig D., Allison N. J., Kam C.-M., Powers J. C. Mol. Immunol. 26:1989;793-798.
15. Hudig D., Allison N. J., Pickett T. M., Winkler U., Kam C., Powers J. C. J. Immunol. 147:1991;1360-1368.
16. Hudig D., Gregg N. J., Kam C.-M., Powers J. C. Biochem. Biophys. Res. Commun. 149:1987;882-888.
17. Zunino S. J., Allison N. J., Kam C., Powers J. C., Hudig D. Biochim. Biophys. Acta. 967:1988;331-340.
18. Odake S., Kam C.-M., Poe M., Tschopp J., Powers J. C. Smith J. A., Rivier J. E. Peptides: Chemistry and Biology, Proceedings of the Twelfth American Peptide Symposium. 1992;857-858 ESCOM, Leiden.
19. Hudig D., Redelman D., Minning L. J. Immunol. 133:1984;2647-2654.
20. Shi L., Kam C.-M., Powers J. C., Aebersold R., Greenberg A. H. J. Exp. Med. 176:1992;1521-1529.
21. Oleksyszyn J., Powers J. C. Biochemistry. 30:1991;485-493.
22. Oleksyszyn J., Powers J. C. Methods Enzymol. 244:1994;442-457.
23. J. C. Powers, S. Odake, J. Oleksyszyn, H. Hori, T. Ueda, B. Boduszek, C.-M. Kam, 1993, Proteases, Protease Inhibitors and Protease-Derived Peptides, J. C. CheronisJ. E. Repine, 3, 19, Birkhäuser Verlag, Basel.
24. Oleksyszyn J., Boduszek B., Kam C.-M., Powers J. C. J. Med. Chem. 37:1994;226-231.
25. Hamilton R., Walker B. J., Walker B. Tetrahedron Lett. 34:1993;2847-2850.
26. Wang D.-L., Taylor T. L., Mical A. J., Spitz S., Reilly T. M. Tetrahedron Lett. 33:1992;7667-7670.
27. Oleksyszyn J., Subotkowska L., Mastalerz P. Synthesis. 1979;985-986.
28. Kam C.-M., Abuelyaman A. S., Li Z., Hudig D., Powers J. C. Bioconjugate Chem. 4:1993;560-567.
29. Honig M. L., Weil E. D. J. Org. Chem. 42:1977;379-381.
30. Borregard N., Heiple J. M., Simons E. R., Clark R. A. J. Cell. Biol. 97:1983;52-61.
31. Ward J. M., Reynolds C. W. Am. J. Pathol. 111:1983;1-11.
32. Pross H. F., Baines M. G., Rubin P., Shragge P., Patterson M. S. J. Clin. Immunol. 1:1981;51-63.
33. Tanaka T., Minematsu Y., Reilly C. F., Travis J., Powers J. C. Biochemistry. 24:1985;2040-2047.
34. Bieth J., Siess B., Wermuth C. G. Biochem. Med. 11:1974;350-357.
35. Nakajima K., Powers J. C., Ashe B. M., Zimmerman M. J. Biol. Chem. 254:1979;4027-4032.
36. Erlanger B. F., Kokowsky N., Cohen W. Arch. Biochem. Biophys. 95:1961;271-278.
37. Woodard S. L., Jackson D. S., Abuelyaman A. S., Powers J. C., Winkler U., Hudig D. J. Immunol. 153:1994;5016-5025.
38. Powers J. C., Tanaka T., Harper J. W., Minematsu Y., Barker L., Lincoln D., Crumley K. V., Fraki J. E., Schechter N. M., Lazarus G. G., Nakajima K., Nakashino K., Neurath H., Woodbury R. G. Biochemistry. 24:1985;2048-2058.
39. Bieth J., Wermuth C. G. Biochem. Biophys. Res. Commun. 53:1973;383-390.
40. Winkler U., Pickett T. M., Hudig D. J. Immunol. Methods. 1996.
41. Abuelyaman A. S., Hudig D., Woodard S. L., Powers J. C. Bioconjugate Chem. 5:1994;400-405.