Identification of a new class of nonpeptidic inhibitors of cruzain

Journal of the American Chemical Society

Volumn 130, Issue 20, 2008, Pages 6404-6410

  Brak, Katrien ^a   Doyle, Patricia S ^b   McKerrow, James H ^b   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CHEMOTHERAPY; DISEASE CONTROL; KETONES;

NONPEPTIDIC INHIBITORS; SUBSTRATE ACTIVITY SCREENING (SAS);

PEPTIDES;

2,3,5,6 TETRAFLUOROPHENOXYMETHYLKETONE; ANTITRYPANOSOMAL AGENT; CATHEPSIN S; CRUZIPAIN; CYSTEINE PROTEINASE; PROTEINASE INHIBITOR; PROTOZOAL PROTEIN;

ANIMAL CELL; ANIMAL CELL CULTURE; ANTIPROTOZOAL ACTIVITY; ARTICLE; CHAGAS DISEASE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG MECHANISM; DRUG POTENCY; DRUG TARGETING; MAMMAL CELL; NONHUMAN; PHARMACOPHORE; PROTEIN BINDING; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA CRUZI;

AMINO ACID SEQUENCE; ANIMALS; CATHEPSINS; COUMARINS; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; DRUG DESIGN; KETONES; MACROPHAGES; MICE; MOLECULAR SEQUENCE DATA; PROTOZOAN PROTEINS; SEQUENCE ALIGNMENT; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES; TRIAZOLES; TRYPANOSOMA CRUZI;

EID: 43949095150     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710254m     Document Type: Article

References (27)

1. http://www.who.int/tdr/diseases/chagas/direction.htm.
2. de Castro, S. L. Acta Trop. 1993, 53, 83-98.
3. Harth, G.; Andrews, N.; Mills, A. A.; Engel, J. C.; Smith, R.; McKerrow, J. H. Mol. Biochem. Parasitol. 1993, 58, 17-24.
4. Engel, J. C.; Doyle, P. S.; Hsieh, I.; McKerrow, J. H. J. Exp. Med. 1998, 188, 725-734.
5. Barr, S. C.; Warner, K. L.; Kornreic, B. G.; Piscitelli, J.; Wolfe, A.; Benet, L.; McKerrow, J. H. Antimicrob. Agents Chemother. 2005, 49, 5160-5161.
6. McKerrow, J. H.; Engel, J. C.; Caffrey, C. R. Biorg. Med. Chem. 1999, 7, 639-644.
7. McKerrow, J. H.; McGrath, M. E.; Engel, J. C. Parasitol. Today 1995, 11, 279-282.
8. Jacobsen, W.; Christians, U.; Benet, L. Z. Drug Metab. Dispos. 2000, 28, 1343-1351.
9. For the only other report of nonpeptidic cruzain inhibitors, see: Du, X.; Guo, C.; Hansell, E.; Doyle, P. S.; Caffrey, C. R.; Holler, T. P.; McKerrow, J. H.; Cohen, F. E. J. Med. Chem. 2002, 45, 2695-2707.
10. Wood, W. J. L.; Patterson, A. W.; Tsuruoka, H.; Jain, R. K.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 15521-15527.
11. Salisbury, C. M.; Ellman, J. A. ChemBioChem 2006, 7, 1034-1037.
12. Patterson, A. W.; Wood, W. J. L.; Hornsby, M.; Lesley, S.; Spraggon, G.; Ellman, J. A. J. Med. Chem. 2006, 49, 6298-6307.
13. Inagaki, H.; Tsuruoka, H.; Hornsby, M.; Lesley, S. A.; Spraggon, G.; Ellman, J. A. J. Med. Chem. 2007, 50, 2693-2699.
14. Soellner, M. B.; Rawls, K. A.; Grundner, C.; Alber, T.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 9613-9615.
15. Bromme, D.; McGrath, M. E. Protein Sci. 1996, 5, 789-791.
16. Palmer, J. T.; Rasnick, D.; Klaus, J. L.; Bromme, D. J. Med. Chem. 1995, 38, 3193-3196.
17. Roush, W. R.; Gwaltney, S. L.; Cheng, J.; Scheidt, K. A.; McKerrow, J. H.; Hansell, E. J. Am. Chem. Soc. 1998, 120, 10994-10995.
18. For an example of vinyl sulfone inhibitors of cruzain with reversible nature, see: Scheidt, K. A.; Roush, W. R.; McKerrow, J. H.; Selzer, P. M.; Hansell, E.; Rosenthal, P. J. Biorg. Med. Chem. 1998, 6, 2477-2494.
19. Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Chem. Rev. 2002, 102, 4639-4750.
20. Govardhan, C. P.; Abeles, R. H. Arch. Biochem. Biophys. 1996, 330, 110-114.
21. Smith, R. A.; Copp, L. J.; Coles, P. J.; Pauls, H. W.; Robinson, V. J.; Spencer, R. W.; Heard, S. B.; Krantz, A. J. Am. Chem. Soc. 1988, 110, 4429-4431.
22. Krantz, A.; Copp, L. J.; Coles, P. J.; Smith, R. A.; Heard, S. B. Biochemistry 1991, 30, 4678-4687.
23. Krantz, A. Methods Enzymol. 1994, 244, 656-671.
24. Bieth, J. G. Methods Enzymol. 1995, 248, 59-84.
25. For an analysis of the rate of inactivation dependence on leaving group orientation for caspases, see : Brady, K. D.; Giegel, D. A.; Grinnell, C.; Lunney, E.; Talanian, R. V.; Wong, W.; Walker, N. Biorg. Med. Chem. 1999, 7, 621-631.
26. Brady, K. D. Biochemistry 1998, 37, 8508-8515.
27. Linton, S. D.; et al. J. Med. Chem. 2005, 48, 6779-6782.