Trypanocidal nitroimidazole derivatives: Relationships among chemical structure and genotoxic activity

Biochemical Pharmacology

Volumn 73, Issue 10, 2007, Pages 1537-1547

  Buschini, Annamaria ^a   Giordani, Federica ^a   de Albuquerque, Cristina Northfleet ^b   Pellacani, Claudia ^a   Pelosi, Giorgio ^a   Rossi, Carlo ^a   Zucchi, Tânia Maria Araújo Domingues ^b   Poli, Paola ^a,b  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

5 Nitromegazol; Benznidazole; Comet assay; Oxidatively damaged DNA; Thiadiazole 5 nitrofuran; Thiosemicarbazone

Indexed keywords

1 METHYL 5 NITRO 2 IMIDAZOLECARBOXALDEHYDE THIOSEMICARBAZONE; 4 NITROMEGAZOL; 5 NITROIMIDAZOLE THIOSEMICARBAZONE; 5 NITROMEGAZOL; BENZNIDAZOLE; ENDONUCLEASE; HYDRAZINE; NITROIMIDAZOLE DERIVATIVE; THIOSEMICARBAZONE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; COMET ASSAY; CONTROLLED STUDY; DNA DAMAGE; DRUG STRUCTURE; GENOTOXICITY; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKOCYTE; OXIDATIVE STRESS; PRIORITY JOURNAL;

CELL SURVIVAL; DNA DAMAGE; DNA FRAGMENTATION; HUMANS; LEUKOCYTES; NITROIMIDAZOLES; TRYPANOCIDAL AGENTS;

EID: 34047273190     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2007.01.024     Document Type: Article

References (48)

1. WHO. Control of Chagas disease. Second Report of the WHO Expert Committee. World Health Organ Tech Rep Ser 905 (2002) 1-115
2. Cançado J.R. Tratamento específico. In: Cançado J.R., and Chuster M. (Eds). Cardiopatía Chagásica. Fundação Carlos Chagas (1985), Belo Horizonte, Brazil 327-355
3. Ferreira H.O. Tratamento da forma indeterminada da doença de Chagas com nifurtimox e benzonidazol. Rev Soc Bras Med Trop 23 (1990) 209-211
4. Galvão L.M., Nunes R.M., Cançado J.R., Brener Z., and Krettli A.U. Lytic antibody titre as means of assessing cure after treatment of Chagas disease: a 10 years follow-up study. Trans R Soc Trop Med Hyg 87 (1993) 220-223
5. Cançado J.R. Long term evaluation of etiological treatment of Chagas disease with benznidazole. Rev Inst Med Trop Sao Paulo 44 (2002) 29-37
6. Filardi L.S., and Brener Z. Susceptibility and natural resistance of Tripanosoma cruzi strains to drugs used clinically in Chagas disease. Trans R Soc Trop Med Hyg 81 (1987) 755-759
7. Veloso V.M., Carneiro C.M., Toledo M.J., Lana M., Chiari E., Tafuri W.L., et al. Variation in susceptibility to benznidazole in isolates derived from Trypanosoma cruzi parental strains. Mem Inst Oswaldo Cruz 96 (2001) 1005-1011
8. Castro J.A. Contributions of toxicology to the problem of Chagas' disease (American trypanosomiasis). A year 2000 update. Biomed Environ Sci 13 (2000) 271-279
9. Raether W., and Hänel H. Nitroheterocyclic drugs with broad spectrum activity. Parasitol Res 90 (2003) S19-S39
10. Voogd C.E., Van der Stel J.J., and Jacobs J.J. The mutagenic action of nitroimidazoles. II. Effects of 2-nitroimidazoles. Mutat Res 31 (1975) 149-152
11. Melo M.E., and Ferreira L.C. Screening the mutagenic activities of commonly used antiparasite drugs by the Simultes, a simplified Salmonella/microsome plate incorporation assay. Rev Inst Med Trop Sao Paulo 32 (1990) 269-274
12. Gorla N., Diaz Gomez M.I., and Castro J.A. Interaction of benznidazole reactive metabolites with rat liver deoxyribonucleic acid and nuclear proteins. Arch Int Pharmacodyn Ther 280 (1986) 22-31
13. Zahoor A., Lafleur M.V., Knight R.C., Loman H., and Edwards D.I. DNA damage induced by reduced nitroimidazole drugs. Biochem Pharmacol 36 (1987) 3299-3304
14. Ferreira R.C.C., Schwarz U., and Ferreira L.C.S. Activation of anti-Trypanosoma cruzi drugs to genotoxic metabolites promoted by mammalian microsomal enzymes. Mutat Res 204 (1988) 577-583
15. Kaneshima E.N., and de Castro-Prado M.A. Benznidazole-induced genotoxicity in diploid cells of Aspergillus nidulans. Mem Inst Oswaldo Cruz 100 (2005) 325-329
16. Santos S.J., Takahashi C.S., and Natarajan A.T. Cytogenetic effects of the antichagasic benznidazole on human cells in vitro. Mutat Res 320 (1994) 305-314
17. Moya P.R., and Trombotto G.T. Enfermedade de Chagas: Efecto clastogenico de nifurtimox y benznidazol en niños. Medicina 48 (1988) 487-491
18. Lacava Z.G., and Luna H. The anticlastogenic effect of tocopherol in peritoneal macrophages of benznidazole-treated and ovariectomized mice. Mutat Res 305 (1994) 145-150
19. Benigni R. Structure-activity relationship studies of chemical mutagens and carcinogens: mechanistic investigations and prediction approaches. Chem Rev 105 (2005) 1767-1800
20. Bouteille B., Marie-Daragon A., Chauvière G., De Albuquerque C., Enanga B., Dardé M.-L., et al. Effect of megazol on Trypanosoma brucei brucei acute and subacute infections in Swiss mice. Acta Trop 60 (1995) 73-80
21. Enanga B., Keita M., Chauvière G., Dumas M., and Bouteille B. Megazol combined with suramin: a chemotherapy regimen which reversed the CNS pathology in a model of human African trypanosomiasis in mice. Trop Med Int Health 3 (1998) 736-741
22. Viodé C., Bettache N., Cenas N., Krauth-Siegel R.L., Chauvière G., Bakalara N., et al. Enzymatic reduction studies of nitroheterocycles. Biochem Pharmacol 57 (1999) 549-557
23. Chauvière G., Bouteille B., Enanga B., de Albuquerque C., Croft S.L., Dumas M., et al. Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead. J Med Chem 46 (2003) 427-440
24. Docampo R., and Moreno S.N. Free radical metabolites in the mode of action of chemotherapeutic agents and phagocytic cells on Trypanosoma cruzi. Rev Infect Dis 6 (1984) 223-238
25. Tsuhako M.H., Alves M.J., Colli W., Brener Z., and Augusto O. Restricted bioreductive metabolism of a nitroimidazole-thiadiazole derivative with curative action in experimental Trypanosoma cruzi infections. Biochem Pharmacol 38 (1989) 4491-4496
26. Enanga B., Ariyanayagam M.R., Stewart M.L., and Barrett M.P. Activity of megazol, a trypanocidal nitroimidazole, is associated with DNA damage. Antimicrob Agents Chemother 47 (2003) 3368-3370
27. Maya J.D., Bollo S., Nuñez-Vergara L.J., Squella J.A., Repetto Y., Morello A., et al. Trypanosoma cruzi: effect and mode of action of nitroimidazole and nitrofuran derivatives. Biochem Pharmacol 65 (2003) 999-1006
28. Ferreira R.C., and Ferreira L.C. Mutagenicity of CL 64855, a potent anti-Trypanosoma cruzi drug. Mutat Res 171 (1986) 11-15
29. Poli P., de Mello M.A., Buschini A., Mortara R.A., Northfleet de Albuquerque C., da Silva S., et al. Cytotoxic and genotoxic effects of megazol, an anti-Chagas' disease drug, assessed by different short-term tests. Biochem Pharmacol 64 (2002) 1617-1627
30. Nesslany F., Brugier S., Mouries M.A., Le Curieux F., and Marzin D. In vitro and in vivo chromosomal aberrations induced by megazol. Mutat Res 560 (2004) 147-158
31. Singh N.P., McCoy M.T., Tice R.R., and Schneider E.L. A simple technique for quantitation of low levels of DNA damage in individual cells. Exp Cell Res 175 (1988) 184-191
32. Tice R.R., Agurell E., Anderson D., Burlinson B., Hartmann A., Kobayashi H., et al. Single cell gel/comet assay: guideline for in vitro and in vivo genetic toxicology testing. Environ Mol Mutagen 35 (2000) 206-221
33. Collins A.R., Dobson V.L., Dusinska M., Kennedy G., and Stetina R. The comet assay: what can it really tell us?. Mutat Res 375 (1997) 183-193
34. Horváthová E., Slamenová D., and Gábelová A. Use of single cell gel electrophoresis (comet assay) modifications for analysis of DNA damage. Gen Physiol Biophys 18 (1999) 70-74
35. Du X., Chun Guo C., Hansell E., Doyle P.S., Caffrey C.R., Holler T.P., et al. Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain. J Med Chem 45 (2002) 2695-2707
36. Aguirre G., Boiani L., Cerecetto H., Fernández M., González M., Denicola A., et al. In vitro activity and mechanism of action against the protozoan parasite Trypanosoma cruzi of 5-nitrofuryl containing thiosemicarbazones. Bioorg Med Chem 12 (2004) 4885-4893
37. Merk O., and Speit G. Detection of crosslinks with the comet assay in relationship to genotoxicity and cytotoxicity. Environ Mol Mutagen 33 (1999) 167-172
38. Buschini A., Alessandrini C., Martino A., Pasini L., Rizzoli V., Carlo-Stella C., et al. Bleomycin genotoxicity and amifostine (WR-2721) cell protection in normal leukocytes vs. K562 tumoral cells. Biochem Pharmacol. 63 (2002) 967-975
39. Collins A.R., Ma A.G., and Duthie S.J. The kinetics of repair of oxidative DNA damage (strand breaks and oxidised pyrimidines) in human cells. Mutat Res 336 (1995) 69-77
40. Fortini P., Raspaglio G., Falchi M., and Dogliotti E. Analysis of DNA alkylation damage and repair in mammalian cells by the comet assay. Mutagenesis 11 (1996) 169-175
41. Benítez-Bribiesca L., and Sánchez-Suárez P. Oxidative damage, bleomycin, and gamma radiation induce different types of DNA strand breaks in normal lymphocytes and thymocytes. A comet assay study. Ann NY Acad Sci 887 (1999) 133-149
42. Pouget J.P., Douki T., Richard M.J., and Cadet J. DNA damage induced in cells by gamma and UVA radiation as measured by HPLC/GC-MS and HPLC-EC and Comet assay. Chem Res Toxicol 13 (2000) 541-549
43. Frankenberg-Schwager M. Review of repair kinetics for DNA damage induced in eukaryotic cells in vitro by ionizing radiation. Radiother Oncol 14 (1989) 307-320
44. Banath J.P., Fushiki M., and Olive P.L. Rejoining of DNA single- and double-strand breaks in human white blood cells exposed to ionizing radiation. Int J Radiat Biol 73 (1998) 649-660
45. González Borroto J.I., Pérez Machado G., Creus A., and Marcos R. Comparative genotoxic evaluation of 2-furylethylenes and 5-nitrofurans by using the comet assay in TK6 cells. Mutagenesis 20 (2005) 193-197
46. Re J.L., De Meo M.P., Laget M., Guiraud H., Castegnaro M., Vanelle P., et al. Evaluation of the genotoxic activity of metronidazole and dimetridazole in human lymphocytes by the comet assay. Mutat Res 375 (1997) 147-155
47. Rigol C., Olea-Azar C., Mendizàbal F., Otero L., Gambino D., Gonzàlez M., et al. Electrochemical and ESR study of 5-nitrofuryl-containing thiosemicarbazones antiprotozoal drugs. Spectrochimica Acta A 61 (2005) 2933-2938
48. Barry C.E., Boshoff H.I.M., and Dowd C.S. Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis. Curr Pharm Des 10 (2004) 3239-3262