Novel aza peptide inhibitors and active-site probes of papain-family cysteine proteases

ChemBioChem

Volumn 7, Issue 6, 2006, Pages 943-950

  Verhelst, Steven H L ^a   Witte, Martin D ^a,b   Arastu Kapur, Shirin ^a   Fonovic, Marko ^a,c   Bogyo, Matthew ^a  

^a STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b LEIDEN UNIVERSITY   (Netherlands)

^c JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

Activity based probes; Cysteine proteases; Drug design; Inhibitors; Proteomics

Indexed keywords

AZAGLYCINE; CATHEPSIN INHIBITOR 3; CYSTEINE PROTEINASE; FALCIPAIN 1; GLYCINE DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; HYDROXYUREA; MW 2; MW 20; MW 21; MW 22; MW 23; MW 4; MW 6; O ACYLHYDROXAMIC ACID DERIVATIVE; O ACYLHYDROXYUREA; PAPAIN; PROTEINASE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; YA 29;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; MOLECULAR PROBE; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL;

ANIMALS; AZA COMPOUNDS; BINDING SITES; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; LIVER; MOLECULAR PROBES; MOLECULAR STRUCTURE; PAPAIN; PEPTIDES; RATS;

PLASMODIUM FALCIPARUM;

EID: 33745314454     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200600001     Document Type: Article

References (31)

1. For example, see: a) C. Jedeszko, B. F. Sloane, Biol. Chem. 2004, 385, 1017-1027;
2. b) V. Turk, B. Turk, D. Turk, EMBO J. 2001, 20, 4629-4633.
3. Y. Iwata, J. S. Mort, H. Tateishi, E. R. Lee, Arthritis Rheum. 1997, 40, 499-509.
4. J. A. Joyce, A. Baruch, J. Chehade, N. Meyer-Morse, E. Girauto, F.-Y. Tsai, D. C. Greenbaum, J. H. Hager, M. Bogyo, D. Hanahan, Cancer Cell 2004, 5, 443-453.
5. F. Lecaille, J. Kaleta, D. Broemme, Chem. Rev. 2002, 102, 4459-4488.
6. D. C. Greenbaum, A. Baruch, M. Grainger, Z. Bozdech, K. F. Medzihradszky, J. Engel, J. DeRisi, A. A. Holder, M. Bogyo, Science 2002, 298, 2002-2006.
7. H. H. Otto, T. Schirmeister, Chem. Rev. 1997, 97, 133-171.
8. J. C. Powers, J. L. Asgian, O. D. Ekici, K. E. James, Chem. Rev. 2002, 102, 4639-4750.
9. For recent reviews, see: a) D. A. Campbell, A. K. Szardenings, Curr. Opin. Chem. Biol. 2003, 7, 296-303;
10. b) J. W. Kozarich, Curr. Opin. Chem. Biol. 2003, 7, 78-83;
11. D. A. Jeffery, M. Bogyo, Curr. Opin. Biotechnol. 2003, 14, 87-95;
12. A. E. Speers, B. F. Cravatt, ChemBioChem 2004, 5, 41-47;
13. e) S. H. L. Verhelst, M. Bogyo, QSAR Comb. Sci. 2005, 24, 261-269.
14. M. Bogyo, S. Verhelst, V. Bellingard-Dubouchaud, S. Toba, D. Greenbaum, Chem. Biol. 2000, 7, 27-38.
15. a) D. C. Greenbaum, W. D. Arnold, F. Lu, L. Hayrapetian, A. Baruch, J. Krumrine, S. Toba, K. Chehade, D. Broemme, I. D. Kuntz, M. Bogyo, Chem. Biol. 2002, 9, 1085-1094;
16. b) D. Greenbaum, A. Baruch, L. Hayrapetian, Z. Darula, A. Burlingame, K. F. Medzihradszky, M. Bogyo, Mol. Cell. Proteomics 2002, 1, 60-68;
17. c) S. H. L. Verhelst, M. Bogyo, ChemBioChem 2005, 6, 824-827.
18. D. Greenbaum, K. F. Medzihradszky, A. Burlingame, M. Bogyo, Chem. Biol. 2000, 7, 569-581.
19. G. Wang, U. Mahesh, G. Y. J. Chen, S. Q. Yao, Org. Lett. 2003, 5, 737-740.
20. a) D. Kato, K. M. Boatright, A. B. Berger, T. Nazif, G. Blum, C. Ryan, K. A. H. Chehade, G. S. Salvesen, M. Bogyo, Nat. Chem. Biol. 2005, 1, 33-38;
21. b) G. Blum, S. R. Mullins, K. Keren, M. Fonovic, C. Jedeszko, M. J. Rice, B. F. Sloane, M. Bogyo, Nat. Chem. Biol. 2005, 1, 203-209.
22. a) D. Broemme, H.-U. Demuth, Methods Enzymol. 1994, 244, 671-685;
23. b) H.-U. Demuth, A. Schierhorn, P. Bryan, R. Hoefke, H. Kirschke, D. Broemme, Biochim. Biophys. Acta 1996, 1295, 179-186.
24. R. Ménard, R. Feng, A. C. Storer, V. J. Robinson, R. A. Smith, A. Krantz, FEBS Lett. 1991, 295, 27-30.
25. a) J. L. Asgian, K. E. James, Z. Z. Li, W. Carter, A. J. Barret, J. Mikolajczyk, G. S. Salvesen, J. C. Powers, J. Med. Chem. 2002, 45, 4958-4960;
26. b) K. E. James, M. G. Götz, C. R. Caffrey, E. Hansell, W. Carter, A. J. Barett, J. H. McKerrow, J. C. Powers, Biol. Chem. 2003, 384, 1613-1618;
27. c) K. E. James, J. L. Asgian, Z. Z. Li, O. D. Ekici, J. R. Rubin, J. Mikolajczyk, G. S. Salvesen, J. C. Powers, J. Med. Chem. 2004, 47, 1553-1574.
28. O. D. Ekici, M. G. Götz, K. E. James, Z. Z. Li, B. J. Rukamp, J. L. Asgian, C. R. Caffrey, E. Hansell, J. Dvorak, J. H. McKerrow, J. Potempa, J. Travis, J. Mikolajczyk, G. S. Salvesen, C. J. Powers, J. Med. Chem. 2004, 47, 1889-1892.
29. S. L. Mellor, C. McGuire, W. C. Chan, Tetrahedron Lett. 1997, 38, 3311-3314.
30. M. Quibell, W. G. Turnell, T. Johnson, J. Chem. Soc. Perkin Trans. 1 1993, 2843-2849.
31. D. Kato, S. H. L. Verhelst, K. B. Sexton, M. Bogyo, Org. Lett. 2005, 7, 5649-5652.