In Vitro and in Vivo activities of 1,3,4-thiadiazole-2-arylhydrazone derivatives of megazol against trypanosoma cruzi

Antimicrobial Agents and Chemotherapy

Volumn 54, Issue 5, 2010, Pages 2023-2031

  Salomao K ^a   De Souza, E M ^a   Carvalho, S A ^a   Da Silva, E F ^a   Fraga, C A M ^b   Barbosa, H S ^a   De Castro, S L ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 THIADIAZOLE 2 ARYLHYDRAZONE; 2 AMINO 5 (1 METHYL 5 NITRO 2 IMIDAZOLYL) 1,3,4 THIADIAZOLE; 3 HYDROXY 4 METHOXYBENZALDEHYDE; 3,5 DITERTBUTYL 4 HYDROXYBENZALDEHYDE; 4 BROMOBENZALDEHYDE; 4 CHLOROBENZALDEHYDE; 4 HYDROXYBENZALDEHYDE; 4 NITROBENZALDEHYDE; ALANINE AMINOTRANSFERASE; ANTIPARASITIC AGENT; ASPARTATE AMINOTRANSFERASE; PROTOCATECHUALDEHYDE; SALICYLALDEHYDE; UNCLASSIFIED DRUG; UREA;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; AMASTIGOTE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; CELL NUCLEUS MEMBRANE; CHAGAS DISEASE; CONTROLLED STUDY; DISEASE COURSE; DRUG POTENCY; DRUG SCREENING; EMBRYO; EXPERIMENTAL MODEL; HEART MUSCLE CELL; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; MACROPHAGE; MALE; MORTALITY; MOUSE; NONHUMAN; PRIORITY JOURNAL; SINGLE DRUG DOSE; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE; UREA BLOOD LEVEL;

ALANINE TRANSAMINASE; ANIMALS; ANTIPROTOZOAL AGENTS; ASPARTATE AMINOTRANSFERASES; BODY WEIGHT; CELLS, CULTURED; CHAGAS DISEASE; HYDRAZONES; INHIBITORY CONCENTRATION 50; MACROPHAGES, PERITONEAL; MALE; MICE; MICROSCOPY, ELECTRON, SCANNING; MYOCYTES, CARDIAC; PARASITEMIA; THIADIAZOLES; TRYPANOSOMA CRUZI; UREA;

EID: 77951228077     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01241-09     Document Type: Article

References (43)

1. Aguirre, G., M. Bolani, H. Cerecetto, A. Gerpe, M. Gonzalez, Y. F. Sainz, A. Denicola, C. O. Ocariz, J. J. Nogal, D. Montero, and J. A. Escario. 2004. Novel antiprotozoal products: imidazole and benzimidazole N-oxide derivatives and related compounds. Arch. Pharm. 337:259-270.
2. Barrett, M. P., A. H. Fairlamb, B. Rousseau, G. Chauvière, and J. Périé. 2000. Uptake of the nitroimidazole drug megazol by African trypanosomes. Biochem. Pharmacol. 59:615-620.
3. Boechat, N., A. S. Carvalho, E. Fernandez-Ferreira, R. O. Soares, A. S. Souza, D. Gibaldi, M. Bozza, and A. C. Pinto. 2001. Novel nitroimidazoles with trypanocidal and cell growth inhibition activities. Cytobios 105:83-90.
4. Bouteille, B., A. Marie-Daragon, G. Chauvière, C. Albuquerque, B. Enanga, M. L. Darde, J. M. Vallat, J. Périé, and M. Dumas. 1995. Effect of megazol on Trypanosoma brucei brucei acute and subacute infections in Swiss mice. Acta Trop. 60:73-80.
5. Brener, Z. 1962. Therapeutic activity and criterion of cure on mice experimentally infected with Trypanosoma cruzi. Rev. Inst. Med. Trop. São Paulo 4:386-396.
6. Carvalho, A. S., R. F. S. Menna-Barreto, N. C. Romeiro, S. L. De Castro, and N. Boechat. 2007. Design, synthesis and activity against Trypanosoma cruzi of azaheterocyclic analogues of megazol. Med. Chem. 3:460-465.
7. Carvalho, S. A., F. A. S. Lopes, K. Salomão, N. C. Romeiro, S. M. V. S. Wardell, S. L. de Castro, E. F. Silva, and C. A. M. Fraga. 2008. Studies toward the structural optimization of new brazilizone-related trypanocidal 1,3,4-thiadiazole-2-arylhydrazone derivatives. Bioorg. Med. Chem. 16:413-421.
8. Carvalho, S. A., E. F. Silva, R. M. Santa-Rita, S. L. de Castro, and C. A. M. Fraga. 2004. Synthesis and antitrypanosomal profile of new functionalyzed 1,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues. Bioorg. Med. Chem. Let. 14:5967-5970.
9. Cerecetto, H., R. Di Maio, M. González, M. Risso, G. Sagrera, G. Seoane, A. Denicola, G. Peluffo, C. Quijano, A. O. M. Stoppani, M. Paulino, C. Olea-Azar, and M. A. Basombrío. 2000. Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2- carboxaldehyde semicarbazone derivatives. Structure-activity relationships. Eur. J. Med. Chem. 35:343-350.
10. Chagas, C. 1909. Nova tripanosomíase humana - estudos sobre a morfologia e o ciclo evolutivo de Schizotrypanum cruzi gen. nov. sp. nov., agente etiológico de nova entidade mórbida do homem. Mem. Inst. Oswaldo Cruz 1:159-218.
11. Chauvière, G., B. Bouteille, B. Enanga, C. Albuquerque, S. L. Croft, M. Dumas, and J. Périé. 2003. Synthesis and biological activity of nitro heterocycles analogs to megazol, a trypanocidal lead. J. Med. Chem. 46:427-440.
12. De Castro, S. L., and M. N. L. Meirelles. 1987. Effect of drugs on Trypanosoma cruzi and on its interaction with heart muscle cell in vitro. Mem. Inst. Oswaldo Cruz 82:209-218.
13. de Castro, S. L., and M. N. L. Meirelles. 1990. Mechanism of action of a nitroimidazole-thiadiazole derivative upon Trypanosoma cruzi tissue culture amastigotes. Mem. Inst. Oswaldo Cruz 85:95-99.
14. de Souza, E. M., G. Melo, D. W. Boykin, A. Kumar, Q. Hu, and M. N. C. Soeiro. 2006. Trypanocidal activity of the phenyl-substituted analogue of furamidine DB569 against Trypanosoma cruzi infection in vivo. J. Antimicrob. Chemother. 58:610-614.
15. Du, X., C. Guo, E. Hansell, P. S. Doyle, C. R. Caffrey, T. P. Holler, J. H. McKerrow, and F. E. Cohen. 2002. Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain. J. Med. Chem. 45:2695-2707.
16. Ferreira, R. C., and L. C. Ferreira. 1986. Mutagenicity of CL 64855, a potent anti-Trypanosoma cruzi drug. Mut. Res. 171:11-15.
17. Filardi, L. S., and Z. Brener. 1982. A nitroimidazole-thiadiazole derivative with curative action in experimental Trypanosoma cruzi infections. Ann. Trop. Med. Parasitol. 76:293-297.
18. Gonzales-Perdomo, M., S. L. de Castro, M. N. L. Meirelles, and S. Goldenberg. 1990. Trypanosoma cruzi proliferation and differentiation are blocked by topoisomerase II inhibitors. Antimicrob. Agents Chemother. 34:1707-1714.
19. Jannin, J., and L. Villa. 2007. An overview of Chagas disease treatment. Mem. Inst. Oswaldo Cruz 102:95-97.
20. Kerschmann, R. L., J. S. Wolfson, G. L. McHugh, G. R. Dickersin, D. C. Hooper, and M. N. Swartz. 1989. Novobiocin-induced ultrastructural changes and antagonism of DNA synthesis in Trypanosoma cruzi amastigotes growing in cell-free medium. J. Protozool. 36:14-20.
21. Lages-Silva, E., L. S. Filardi, and Z. Brener. 1990. Effect of the host specific treatment in the phagocytosis of Trypanosoma cruzi blood forms by mouse peritoneal macrophages. Mem. Inst. Oswaldo Cruz 85:401-405.
22. Mahy, J. P., S. Gaspard, and D. Mansuy. 1993. Phenylhydrazones as new good substrates for the dioxygenase and peroxidase reactions of prostaglandin synthase: formation of iron(III)-sigma-phenyl complexes. Biochemistry 32:4014-4021.
23. Maya, J. D., S. Bollo, L. J. Nunez-Vergara, J. A. Squella, Y. Repetto, A. Morello, J. Périé, and G. Chauvière. 2003. Trypanosoma cruzi: effect and mode of action of nitroimidazole and nitrofuran derivatives. Biochem. Pharmacol. 65:999-1006.
24. Meirelles, M. N. L., T. C. Araujo-Jorge, C. F. Miranda, W. de Souza, and H. S. Barbosa. 1986. Interaction of Trypanosoma cruzi with heart muscle cells: ultrastructural and cytochemical analysis of endocytic vacuole formation and effect upon myogenesis in vitro. Eur. J. Cell Biol. 41:198-206.
25. Menezes, D., C. Valentim, M. F. Oliveira, and M. A. Vannier-Santos. 2006. Putrescine analogue cytotoxicity against Trypanosoma cruzi. Parasitol. Res. 98:99-105.
26. Messeder, J. C., W. Tinoco, J. D. Figueroa-Villar, E. M. de Souza, R. M. Santa-Rita, and S. L. de Castro. 1995. Aromatic guanylhydrazones: Synthesis, structural studies and in vitro activity against Trypanosoma cruzi. Bioorg. Med. Chem. Lett. 24:3079-3084.
27. Mossman, B. T. 1983. In vitro approaches for determining mechanisms of toxicity and carcinogenicity by asbestos in the gastrointestinal and respiratory tracts. Environ. Health Perspect. 53:155-161.
28. Motta, M. C. 2008. Kinetoplast as a potential chemotherapeutic target of trypanosomatids. Curr. Pharm. Des. 14:847-854.
29. Nesslany, F., S. Brugier, M. A. Mouries, F. Le Curieux, and D. Marzin. 2004. In vitro and in vivo chromosomal aberrations induced by megazol. Mut. Res. 560:147-158.
30. Poli, P., M. A. Mello, A. Buschini, R. A. Mortara, C. Albuquerque, S. Silva, C. Rossi, and T. M. Zucchi. 2002. Cytotoxic and genotoxic effects of megazol, an anti-Chagas disease drug, assessed by different short-term tests. Biochem. Pharmacol. 64:1617-1627.
31. Prusis, P., M. Dambrova, V. Andrianov, E. Rozhkov, V. Semenikhina, I. Piskunova, E. Ongwae, T. Lundstedt, I. Kalvinsh, and J. E. Wikberg. 2004. Synthesis and quantitative structure-activity relationship of hydrazones of N-amino-N′-hydroxyguanidine as electron acceptors for xanthine oxidase. J. Med. Chem. 47:3105-3110.
32. Rodriques Coura, J. R., and S. L. De Castro. 2002. A critical review on Chagas disease chemotherapy. Mem. Inst. Oswaldo Cruz 97:3-24.
33. Romanha, A. J., M. N. C. Soeiro, J. Lannes-Vieira, S. L. de Castro, I. Ribeiro, A. Talvani, B. Bourdin, B. Blum, B. Olivieri, C. Zani, C. Spadafora, E. Chiari, E. Chatelain, G. Chaves, J. E. Calzada, J. Bustamante, L. J. Freitas, L. Romero, M. T. Bahia, M. Lotrowska, M. Soares, S. G. Andrade, T. Armstrong, W. Degrave, and Z. A. Andrade. Experimental in vitro and in vivo models for drug screening and development for Chagas disease. Mem. Inst. Oswaldo Cruz, in press.
34. Salomão K., E. M. de Souza, A. Henriques-Pons, H. S. Barbosa, and S. L. De Castro. 11 March 2009. Brazilian green propolis: effects in vitro and in vivo on Trypanosoma cruzi. Evid. Based Complement. Alternat. Med. doi: 10.1093/ecam/nep014.
35. Sant'Anna, C., F. Parussini, D. Lourenço, W. de Souza, J. J. Cazzulo, and N. L. Cunha-e-Silva. 2008. All Trypanosoma cruzi developmental forms present lysosome-related organelles. Histochem. Cell Biol. 130:1187-1198.
36. Schmunis, G. A. 2007. Epidemiology of Chagas disease in non endemic countries: the role of international migration. Mem. Inst. Oswaldo Cruz 102(Suppl. 1):75-85.
37. Sforcin, J. M. 2007. Propolis and the immune system: a review. J. Ethnopharmacol. 113:1-14.
38. Silva, C. F., M. B. Meuser, E. M. de Souza, M. N. L. Meirelles, C. E. Stephens, P. Som, D. W. Boykin, and M. N. C. Soeiro. 2007. Cellular effects of reversed amidines on Trypanosoma cruzi. Antimicrob. Agents Chemother. 51:3803-3809.
39. Soeiro, M. N. C., and S. L. de Castro. 2009. Trypanosoma cruzi targets for new chemotherapeutic approaches. Expert Opin. Ther. Targets 13:105-121.
40. Souto-Padrón, T., W. de Souza, and J. E. Heuser. 1984. Quick-freeze, deep etched rotary replication of Trypanosoma cruzi and Herpetomonas megaseliae. J. Cell Sci. 69:167-178.
41. Souza, E. M., A. Lansiaux, C. Bailly, W. D. Wilson, Q. Hu, D. W. Boykin, M. M. Batista, T. C. Araújo-Jorge, and M. N. C. Soeiro. 2004. Phenyl substitution of furamidine markedly potentiates its anti-parasitic activity against Trypanosoma cruzi and Leishmania amazonensis. Biochem. Pharmacol. 133:593-600.
42. Vannier-Santos, M. A., and S. L. de Castro. 2009. Electron microscopy in antiparasitic chemotherapy: a (close) view to a kill. Curr. Drug Targets 10:246-260.
43. Viodé, C., N. Bettache, N. Cenas, R. L. Krauth-Siegel, G. Chauvière, N. Bakalara, and J. Périé. 1999. Enzymatic reduction studies of nitroheterocycles. Biochem. Pharmacol. 57:549-557.