Novel peptidomimetic cysteine protease inhibitors as potential antimalarial agents

Journal of Medicinal Chemistry

Volumn 49, Issue 11, 2006, Pages 3064-3067

  Micale, Nicola ^a   Kozikowski, Alan P ^b   Ettari, Roberta ^a   Grasso, Silvana ^a   Zappalà, Maria ^a   Jeong, Jong Jin ^c   Kumar, Ajay ^d   Hanspal, Manjit ^d   Chishti, Athar H ^c  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c UNIVERSITY OF ILLINOIS   (United States)

^d ST ELIZABETH'S MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; BENZODIAZEPINE DERIVATIVE; CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; FALCIPAIN 2; FALCIPAIN 2A; FALCIPAIN 2A INHIBITOR; FALCIPAIN 2B; FALCIPAIN 2B INHIBITOR; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG SYNTHESIS; INHIBITION KINETICS; MALARIA; NONHUMAN; PLASMODIUM FALCIPARUM; PROTEINASE INHIBITION;

EID: 33744805804     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060405f     Document Type: Article

References (39)

1. (a) Breman, J. G. The ears of the hippopotamus: manifestations, determinants, and estimates of the malaria burden. Am. J. Trop. Med. Hyg. 2001, 64s, 1-11.
2. (b) Greenwood, B.; Mutabingwa, T. Malaria in 2002. Nature 2002, 415, 670-672.
3. (a) Hyde, J. E. Mechanisms of resistance of Plasmodium falciparum to antimalarial drugs. Microbes Infect. 2002, 4, 165-174.
4. (b) Ridley, R. G. Medical need, scientific opportunity and drive for antimalarial drugs. Nature 2002, 415, 686-693.
5. (a) Rosenthal, P. J. Hydrolysis of erythrocyte proteins by proteases of malaria parasites. Curr. Opin. Hematol. 2002, 9, 140-145.
6. (b) Klemba, M.; Goldberg, D. E. Biological roles of proteases in parasitic protozoa. Annu. Rev. Biochem. 2002, 71, 275-305.
7. (a) Shenai, B. R.; Sijwali, P. S.; Singh, A.; Rosenthal, P. J. Characterization of native and recombinant falcipain-2, a pricipal trophozoite cysteine protease and essential hemoglobinase of Plasmodium falciparum. J. Biol. Chem. 2000, 275, 29000-29010.
8. (b) Dua, M.; Raphael, P.; Sijwali, P. S.; Rosenthal, P. J.; Hanspal, M. Recombinant falcipain-2 cleaves erythrocyte membrane ankyrin and protein 4.1. Mol. Biochem. Parasitol. 2001, 116, 95-99.
9. (c) Hanspal, M.; Dua, M.; Takakuwa, Y.; Chishti, A. H.; Mizuno, A. Plasmodium falciparum cysteine protease falcipain-2 cleaves erythrocyte membrane skeletal proteins at late stages of parasite development. Blood 2002, 100, 1048-1054.
10. (d) Dhawan, S.; Dua, M.; Chishti, A. H.; Hanspal, M. Ankyrin peptide blocks falcipain-2-mediated malaria parasite release from red blood cells. J. Biol. Chem. 2003, 278, 30180-30186.
11. (e) Rosenthal, P. J. Cysteine proteases of malaria parasites. Int. J. Parasitol. 2004, 34, 1489-1499.
12. (a) Nielsen, K. M.; Kasper, J.; Choi, M.; Bedford, T.; Kristiansen, K.; Wirth, D. F.; Volkman, S. K.; Lozovsky, E. R.; Hartl, D. L. Gene conversion as a source of nucleotide diversity in Plasmodium falciparum. Mol. Biol. Evol. 2003, 20, 726-734.
13. (b) Sijwali, P. S. Rosenthal, P. J. Gene disruption confirms a critica role for the cysteine protease falcipain-2 in hemoglobin hydrolysis by Plasmodium falciparum. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 4384-4389.
14. (c) Goh, L. L.; Sim, T. S. Characterization of amino acid variation at strategic positions in parasite and human proteases for selective inhibition of falcipains in Plasmodium falciparum. Biochem. Biophys. Res. Commun. 2005, 335, 762-770.
15. (d) Singh, N.; Sijwali, P. S.; Pandey, K. C.; Rosenthal, P. J. Plasmodium falciparum: Biochemical characterization of the cysteine protease falcipain-2′. Exp. Parasitol. 2006, 112, 187-192.
16. (e) Jeong, J.-J.; Kumar, A.; Hanada, T.; Seo, P.-S.; Li, X.; Hanspal, M.; Chishti, A. H. Cloning and characterization of Plasmodium falciparum cysteine protease, falcipain-2B. Blood Cells, Mol. Dis., in press.
17. Shenai, B. R.; Lee, B. J.; Alvarez-Hernandez, A.; Chong, P. Y.; Emal, C. D.; Neitz, R. J.; Roush, W. R.; Rosenthal, P. J. Structure-activity relationships for inhibition of cysteine protease activity and development of Plasmodium falciparum by peptidyl vinyl sulfones. Antimicrob. Agents Chemother. 2003, 47, 154-160.
18. Rosenthal, P. J.; Wollish, W. S.; Palmer, J. T.; Rasnick, D. Antimalarial effects of peptide inhibitors of a Plasmodium falciparum cysteine proteinase. J. Clin. Invest. 1991, 88, 1467-1472.
19. Lee, B. J.; Singh, A.; Chiang, P.; Kemp, S. J.; Goldman, E. A.; Weinhouse, M. I.; Vlasuk, G. P.; Rosenthal, P. J. Antimalarial activities of novel synthetic cysteine protease inhibitors. Antimicrob. Agents Chemother. 2003, 47, 3810-3814.
20. Leung-Toung, R.; Li, W.; Tamn, T. F.; Karimian, K. Thiol-dependent enzymes and their inhibitors: a review. Curr. Med. Chem. 2002, 9, 979-1002
21. (a) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. Concepts and progress in the development of peptide mimetics. J. Med. Chem. 1993, 36, 3039-3049.
22. (b) Fairlie, D. P.; Abbenante, G.; March, D. R. Macrocyclic peptidomimetics. Forcing peptides into bioactive conformations. Curr. Med Chem. 1995, 2, 654-686.
23. (a) Golec, J. M. C.; Lauffer, D. J.; Livingston, D. J.; Mullican, M. D.; Murcko, M. A.; Nyce, P. L.; Robidoux, A. L. C.; Wannamaker, M. W. Inhibitors of Interleukin-1β Converting Enzyme. Patent WO 9824805, 1998.
24. 2 receptor agonists containing constrained dipeptide mimics. J. Med. Chem. 1999, 42, 4193-4201.
25. 2 receptor antagonists employing the benzodiazepine peptidomimetic scaffold. Bioorg. Med. Chem. Lett. 1999, 9, 463-468.
26. Rotonda, J.; Nicholson, D. W.; Fazil, K. M.; Gallant, M.; Gareau. Y.; Labelle, M.; Peterson, E. P.; Rasper, D. M.; Ruel, R.; Vaillancourt, J. P.; Thornberry, N. A.; Becker, J. W. The three-dimensional structure of apopain/CPP32, a key mediator of apoptosis. Nat. Struct. Biol. 1996, 3, 619-625.
27. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. An improved procedure for the preparation of the Garner aldehyde and its use for the synthesis of N-protected 1-halo-2(R)-amino-3-butenes. Synthesis 1994, 31-33.
28. Graybill, T. L.; Dolle, R. E.; Helaszek, C. T.; Miller, R. E.; Ator, M. A. Preparation and evaluation of peptidic aspartyl hemiacetals as reversible inhibitors of interleukin-1β converting enzyme (ICE). Int. J. Pept. Protein Res. 1994, 44, 173-182.
29. Loidl, G.; Musiol, H. J.; Groll, M.; Huber, R., Moroder, L. Synthesis of bivalent inhibitors of eucaryotic proteasomes. J. Pept. Sci. 2000, 6, 36-46.
30. (a) McConnell, R. M.; Barnes, G. E.; Hoyng, C. F.; Gunn, J. M. New leupeptin analogues: synthesis and inhibition data. J. Med. Chem. 1990, 33, 86-93.
31. (b) Karanewsky, D. S.; Bai, X.; Linton, S. D.; Krebs, J. F.; Wu, J.; Pham, B.; Tomaselli, K. J. Conformationally constrained inhibitors of caspase-1 (interleukin-1β converting enzyme) and of the human ced-3 homologue caspase-3 (CPP-32, apopain). Bioorg. Med. Chem. Lett. 1998, 8. 2757-2762.
32. (a) Linton, S. D.; Karanewsky, D. S.; Ternansky, R. J.; Wu, J. C.; Pham, B.; Kodandapani, L.; Smidt, R.; Diaz, J.-L.; Fritz, L. C.; Tomaselli, K. J. Acyl dipeptides as reversible caspase inhibitors. Part I: initial lead optimization. Bioorg. Med. Chem. Lett. 2002, 12, 2969-2971.
33. (b) Linton, S. D.; Karanewsky, D. S.; Ternansky, R. J.; Chen, N.; Guo, X.; Jahangiri, K. G.; Kalish, V. J.; Meduna, S. P.; Robinson, E. D.; Ullman, B. R.; Wu, J. C.; Pham, B.; Kodandapani, L.; Smidt, R.; Diaz, J.-L.; Fritz, L. C.; Von Krosigk, U.; Roggo, S.; Schmitz, A.; Tomaselli, K. J. Acyl dipeptides as reversible caspase inhibitors. Part 2: further optimization. Bioorg. Med. Chem. Lett. 2002, 12, 2973-2975.
34. (a) Patel, R. H.; Ahsan, A.; Suthar, B. P.; Schultz, R. M. Transition-state affinity chromatography of trypsin-like proteinases with dipeptidyl argininal ligands. Biochim. Biophys. Acta 1983, 748, 321-330.
35. (b) Murphy, A. M.; Dagnino, R.; Vallar, P. L.; Trippe, A. J.; Sherman, S. L.; Lumpkin, R. H.; Tamura, S. Y.; Webb, T. R. Automated synthesis of peptide C-terminal aldehydes J. Am. Chem. Soc. 1992, 114, 3156-3157.
36. (a) Fehrentz, J. A.; Castro, B. An efficient synthesis of optically active α-t-butoxycarbonylamino-aldehydes from α-amino acids. Synthesis 1983, 676-678.
37. (b) Nahm, S.; Weinred, S. N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett. 1981, 22, 3815-3818.
38. Mehdi, S.; Angelastro, M. R.; Wiseman, J. S.; Bey, P. Inhibition of the proteolysis of rat erythrocyte membrane proteins by a synthetic-inhibitor of calpain. Biochem. Biophys. Res. Commun. 1988, 157, 1117-1123.
39. Micale, N.; Vairagoundar, R.; Yakovlev, A. G.; Kozikowski, A. P. Design and synthesis of a potent and selective peptidomimetic inhibitor of caspase-3. J. Med. Chem. 2004, 47, 6455-6458.