Arylimidamide DB766, a potential chemotherapeutic candidate for Chagas' disease treatment

Antimicrobial Agents and Chemotherapy

Volumn 54, Issue 7, 2010, Pages 2940-2952

  Batista, Denise Da Gama Jaén ^a   Batista, Marcos Meuser ^a   De Oliveira, Gabriel Melo ^a   Do Amaral, Patrícia Borges ^a   Lannes Vieira, Joseli ^a   Britto, Constança Carvalho ^a   Junqueira, Angela ^a   Lima, Marli Maria ^a   Romanha, Alvaro José ^a   Sales Jr , Policarpo Ademar ^a   Stephens, Chad E ^b   Boykin, David W ^c   Soeiro, Maria De Nazaré Correia ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b AUGUSTA STATE UNIVERSITY   (United States)

^c GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ARYLIMIDAMIDE; BENZNIDAZOLE; DB 766; UNCLASSIFIED DRUG; 2,5-BIS(2-(2-PROPOXY)-4-(2-PYRIDYLIMINO)AMINOPHENYL)FURAN; AMIDINE; ANTITRYPANOSOMAL AGENT; FURAN DERIVATIVE;

AMASTIGOTE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMICROBIAL ACTIVITY; ARTICLE; CHAGAS DISEASE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFICACY; DRUG SELECTIVITY; FEMALE; FLUORESCENCE MICROSCOPY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; TOXICITY TESTING; TRANSMISSION ELECTRON MICROSCOPY; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE; ANIMAL; C3H MOUSE; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ELECTROCARDIOGRAPHY; PARASITOLOGY; PATHOLOGY; PHYSIOLOGY; ULTRASTRUCTURE;

AMIDINES; ANIMALS; CELLS, CULTURED; CHAGAS DISEASE; ELECTROCARDIOGRAPHY; FEMALE; FURANS; MALE; MICE; MICE, INBRED C3H; MICROSCOPY, ELECTRON, TRANSMISSION; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

EID: 77953782964     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01617-09     Document Type: Article

References (73)

1. Aguilar, H. M., F. Abad-Franch, J. C. Dias, A. C. Junqueira, and J. R. Coura. 2007. Chagas disease in the Amazon region. Mem. Inst. Oswaldo Cruz 102(Suppl. 1):47-56.
2. Alencar, J. E. 1987. Historia Natural da Doença de Chagas no Estado do Ceará. Ph.D. thesis. Universidade Federal do Ceará, Fortaleza, Brazil.
3. Andrade, L. O., C. R. Machado, E. Chiari, S. D. Pena, and A. M. Macedo. 1999. Differential tissue distribution of diverse clones of Trypanosoma cruzi in infected mice. Mol. Biochem. Parasitol. 100:163-172.
4. Basselin, M., F. Lawrence, and M. Robert-Gero. 1996. Pentamidine uptake in Leishmania donovani and Leishmania amazonensis promastigotes and axenic amastigotes. Biochem. J. 315:631-634.
5. Batista, D. G. J., M. G. O. Pacheco, A. Kumar, D. Branowska, M. Ismail, L. Hu, D. W. Boykin, and M. N. Soeiro. 2009. Biological, ultrastructural effect and subcellular localization of aromatic diamidines in Trypanosoma cruzi. Parasitology 21:1-9.
6. Bettiol, E., M. Samanovic, A. S. Murkin, J. Raper, F. Buckner, and A. Rodriguez. 2009. Identification of three classes of heteroaromatic compounds with activity against intracellular Trypanosoma cruzi by chemical library screening. PLoS Negl. Trop. Dis. 3:e384.
7. Bilate, A. M., and E. Cunha-Neto. 2008. Chagas disease cardiomyopathy: current concepts of an old disease. Rev. Inst. Med. Trop. São Paulo 50:67-74.
8. Brener, Z. 1962. Therapeutic activity and criterion of cure on mice experimentally infected with Trypanosoma cruzi. Rev. Inst. Med. Trop. São Paulo 4:389-396.
9. Britto, C. C. 2009. Usefulness of PCR-based assays to assess drug efficacy in Chagas disease chemotherapy: value and limitations. Mem. Inst. Oswaldo Cruz 104(Suppl. I):122-135.
10. Britto, C., M. A. Cardoso, P. Wincker, and C. M. Morel. 1993. A simple protocol for the physical cleavage of Trypanosoma cruzi kinetoplast DNA present in blood samples and its use in polymerase chain reaction (PCR)-based diagnosis of chronic Chagas disease. Mem. Inst. Oswaldo Cruz 88: 171-172.
11. Bronfen, E., F. S. de Assis Rocha, G. B. Machado, M. M. Perillo, A. J. Romanha, and E. Chiari. 1989. Isolation of Trypanosoma cruzi samples by xenodiagnosis and hemoculture from patients with chronic Chagas' disease. Mem. Inst. Oswaldo Cruz 84:237-240.
12. Bustamante, J. M., L. M. Bixby, and R. L. Tarleton. 2008. Drug-induced cure drives conversion to a stable and protective CD8 T central memory response in chronic Chagas disease. Nat. Med. 14:542-550.
13. Croft, S. L., and R. P. Brazil. 1982. Effect of pentamidine isethionate on the ultrastructure and morphology of Leishmania mexicana amazonensis in vitro. Ann. Trop. Med. Parasitol. 76:37-43.
14. Daliry, A., P. B. Silva, C. F. Silva, M. M. Batista, S. L. de Castro, R. R. Tidwell, and M. N. Soeiro. 2009. In vitro analyses of the effect of aromatic diamidines upon Trypanosoma cruzi. J. Antimicrob. Chemother. 64:747-750.
15. da Silva, C. F., M. M. Batista, D. G. J. Batista, E. M. De Souza, P. B. da Silva, G. M. de Oliveira, A. S. Meuser, A. R. Shareef, D. W. Boykin, and M. N. Soeiro. 2008. In vitro and in vivo studies of the trypanocidal activity of a diarylthiophene diamidine against Trypanosoma cruzi. Antimicrob. Agents Chemother. 52:3307-3314.
16. de Castro, S. L., M. N. C. Soeiro, K. O. Higashi, and M. N. L. Meirelles. 1993. Differential effect of amphotericin B on the three evolutive stages of Trypanosoma cruzi and on the host cell-parasite interaction. Braz. J. Med. Biol. Res. 26:1219-1229.
17. de Koning, H. P., D. J. Bridges, and R. J. Burchmore. 2005. Purine and pyrimidine transport in pathogenic protozoa: from biology to therapy. FEMS Microbiol. Rev. 29:987-1020.
18. De 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. Soeiro. 2004. Phenyl substitution of furamidine markedly potentiates its anti-parasitic activity against Trypanosoma cruzi and Leishmania amazonensis. Biochem. Pharmacol. 68: 593-600.
19. De Souza, E. M., G. M. Oliveira, and M. N. C. Soeiro. 2007. Electrocardiographic finding in acutely and chronically Trypanosoma cruzi-infected mice treated by a phenyl-substituted analogue of Furamidine DB569. Drug Target Insights 2:61-69.
20. de Souza, E. M., G. M. Oliveira, 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.
21. Dias, J. C. 2007. Southern Cone Initiative for the elimination of domestic populations of Triatoma infestans and the interruption of transfusion Chagas disease: historical aspects, present situation, and perspectives. Mem. Inst. Oswaldo Cruz 102:11-18.
22. Dias, J. C. P. 2009. Elimination of Chagas disease transmission: perspectives. Mem. Inst. Oswaldo Cruz 104(Suppl. I):41-45.
23. Dias, J. C., A. C. Silveira, and C. J. Schofield. 2002. The impact of Chagas disease control in Latin America: a review. Mem. Inst. Oswaldo Cruz 97:603-612.
24. Dias, J. C., A. Prata, and D. Correia. 2008. Problems and perspectives for Chagas disease control: in search of a realistic analysis. Rev. Soc. Bras. Med. Trop. 41:193-196.
25. dos Santos, P. V., E. Roffê, H. C. Santiago, R. A. Torres, A. P. Marino, C. N. Paiva, A. A. Silva, R. T. Gazzinelli, and J. Lannes-Vieira. 2001. Prevalence of CD8(+)alpha beta T cells in Trypanosoma cruzi-elicited myocarditis is associated with acquisition of CD62L(low)LFA-1(high)VLA-4(high) activation phenotype and expression of IFN-gamma-inducible adhesion and chemoattractant molecules. Microbes Infect. 3:971-984.
26. Dvorak, J. A. 1984. The natural heterogeneity of Trypanosoma cruzi: biological and medical implications. J. Cell. Biochem. 24:357-371.
27. Fernandes, O., R. P. Souto, J. A. Castro, J. B. Pereira, N. C. Fernandes, A. C. Junqueira, R. D. Naiff, T. V. Barrett, W. Degrave, B. Zingales, D. A. Campbell, and J. R. Coura. 1998. Brazilian isolates of Trypanosoma cruzi from humans and triatomines classified into two lineages using mini-exon and ribosomal RNA sequences. Am. J. Trop. Med. Hyg. 58:807-811.
28. Filardi, L. S., and Z. Brener. 1987. Susceptibility and natural resistance of Trypanosoma cruzi strains to drugs used clinically in Chagas disease. Trans. R. Soc. Trop. Med. Hyg. 81:755-759.
29. Fusai, T., Y. Boulard, R. Durand, M. Paul, C. Bories, D. Rivollet, A. Astier, R. Houin, and M. Deniau. 1997. Ultrastructural changes in parasites induced by nanoparticle-bound pentamidine in a Leishmania major/mouse model. Parasite 4:133-139.
30. Gascón, J., P. Albajar, E. Cañas, M. Flores, i Prat. J. Gómez, R. N. Herrera, C. A. Lafuente, H. L. Luciardi, A. Moncayo, L. Molina, J. Muñoz, S. Puente, G. Sanz, B. Treviño, and X. Sergio-Salles. 2007. Diagnosis, management and treatment of chronic Chagas' heart disease in areas where Trypanosoma cruzi infection is not endemic. Rev. Esp. Cardiol. 60:285-293.
31. Guerri-Guttenberg, R. A., D. R. Grana, G. Ambrosio, and J. Milei. 2008. Chagas cardiomyopathy: Europe is not spared! Eur. Heart J. 29:2587-2591.
32. Hall, J. E., J. E. Kerrigan, K. Ramachandran, B. C. Bender, J. P. Stanko, S. K. Jones, D. A. Patrick, and R. R. Tidwell. 1998. Anti-Pneumocystis activities of aromatic diamidoxime prodrugs. Antimicrob. Agents Chemother. 42:666-674.
33. Hentzer, B., and T. Kobayasi. 1977. The ultrastructural changes of Leishmania tropica after treatment with pentamidine. Ann. Trop. Med. Parasitol. 71:157-166.
34. Ismail, M. A., R. K. Arafa, T. Wenzler, R. Brun, F. A. Tanious, W. D. Wilson, and D. W. Boykin. 2008. Synthesis and antiprotozoal activity of novel bisbenzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a] pyridines. Bioorg. Med. Chem. 16:683-691.
35. Lannes-Vieira, J., J. C. Silverio, I. R. Pereira, N. F. Vinagre, C. M. Carvalho, C. N. Paiva, and A. A. da Silva. 2009. Chronic Trypanosoma cruzi-elicited cardiomyopathy: from the discovery to the proposal of rational therapeutic interventions targeting cell adhesion molecules and chemokine receptors-how to make a dream come true. Mem. Inst. Oswaldo Cruz 104:226-235.
36. Marin-Neto, J. A., E. Cunha-Neto, B. C. Maciel, and M. V. Simões. 2007. Pathogenesis of chronic Chagas heart disease. Circulation 115:1109-1123.
37. Mathis, A. M., A. S. Bridges, M. A. Ismail, A. Kumar, I. Francesconi, M. Anbazhagan, Q. Hu, F. A. Tanious, T. Wenzler, J. Saulter, W. D. Wilson, R. Brun, D. W. Boykin, R. R. Tidwell, and J. E. Hall. 2007. Diphenyl furans and aza analogs: effects of structural modification on in vitro activity, DNA binding, and accumulation and distribution in trypanosomes. Antimicrob. Agents Chemother. 51:2801-2810.
38. McKerrow, J. H., P. S. Doyle, J. C. Engel, L. M. Podust, S. A. Robertson, R. Ferreira, T. Saxton, M. Arkin, and I. D. Kerr. 2009. Two approaches to discovering and developing new drugs for Chagas disease. Mem. Inst. Oswaldo Cruz 104(Suppl. I):263-269.
39. Meirelles, M. N., 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.
40. Menna-Barreto, R. F., A. Henriques-Pons, A. V. Pinto, J. A. Morgado-Diaz, M. J. Soares, and S. L. De Castro. 2005. Effect of a beta-lapachone-derived naphthoimidazole on Trypanosoma cruzi: identification of target organelles. J. Antimicrob. Chemother. 56:1034-1041.
41. Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65:55-63. (Pubitemid 14203433)
42. Nóbrega, A. A., M. H. Garcia, E. M. Tatto, T. Obara, E. Costa, J. Sobel, and W. N. Araújo. 2009. Oral transmission of Chagas disease by consumption of açaí palm fruit, Brazil. Emerg. Infect. Dis. 15:653-655.
43. Nozaki, T., and J. A. Dvorak. 1993. Intraspecific diversity in the response of Trypanosoma cruzi to environmental stress. J. Parasitol. 79:451-454.
44. Nwaka, S., and A. Hudson. 2006. Innovative lead discovery strategies for tropical diseases. Nat. Rev. Drug Discov. 5:941-955.
45. Nyunt, M. M., C. W. Hendrix, R. P. Bakshi, N. Kumar, and T. A. Shapiro. 2009. Phase I/II evaluation of the prophylactic antimalarial activity of pafuramidine in healthy volunteers challenged with Plasmodium falciparum sporozoites. Am. J. Trop. Med. Hyg. 80:528-535.
46. Pacheco, M. G., C. F. Silva, E. M. Souza, M. M. Batista, P. B. Silva, A. Kumar, C. E. Stephens, D. W. Boykin, and M. N. Soeiro. 2009. Trypanosoma cruzi: activity of heterocyclic cationic molecules in vitro. Exp. Parasitol. 123:73-80.
47. Pena, S. D., C. R. Machado, and A. M. Macedo. 2009. Trypanosoma cruzi: ancestral genomes and population structure. Mem. Inst. Oswaldo Cruz 104:108-114.
48. Postan, M., J. P. McDaniel, and J. A. Dvorak. 1984. Studies of Trypanosoma cruzi clones in inbred mice. II. Course of infection of C57BL/6 mice with single-cell-isolated stocks. Am. J. Trop. Med. Hyg. 33:236-238.
49. Postan, M., J. P. McDaniel, and J. A. Dvorak. 1987. Comparative studies of the infection of Lewis rats with four Trypanosoma cruzi clones. Trans. R. Soc. Trop. Med. Hyg. 81:415-419.
50. Rodriguez-Morales, A. J., J. A. Benitez, I. Tellez, and C. Franco-Paredes. 2008. Chagas disease screening among Latin American immigrants in nonendemic settings. Travel Med. Infect. Dis. 6:162-163.
51. Rodriques Coura, J., and S. L. De Castro. 2002. A critical review on Chagas disease chemotherapy. Mem. Inst. Oswaldo Cruz 97:3-24.
52. Rosypal, A. C., K. A. Werbovetz, M. Salem, C. E. Stephens, A. Kumar, D. W. Boykin, J. E. Hall, and R. R. Tidwell. 2008. Inhibition by dications of in vitro growth of Leishmania major and Leishmania tropica: causative agents of old world cutaneous leishmaniasis. J. Parasitol. 94:743-749.
53. Salomão, K., E. M. de Souza, A. Henriques-Pons, H. S. Barbosa, and S. L. de Castro. 11 March 2009, posting date. Brazilian green propolis: effects in vitro and in vivo on Trypanosoma cruzi. Evid. Based Complement. Alternat. Med. doi:10.1093/ecam/nep014.
54. Silva, C. F., M. B. Meuser, E. M. De Souza, M. N. Meirelles, C. E. Stephens, P. Som, D. W. Boykin, and M. N. Soeiro. 2007. Cellular effects of reversed amidines on Trypanosoma cruzi. Antimicrob. Agents Chemother. 51:3803-3809.
55. Silva, C. F., M. M. Batista, R. A. Mota, E. M. De Souza, C. E. Stephens, P. Som, D. W. Boykin, and M. N. Soeiro. 2007. Activity of "reversed" diamidines against Trypanosoma cruzi in vitro. Biochem. Pharmacol. 73:1939-1946.
56. Soeiro, M. N. C., A. P. Dantas, A. Daliry, C. F. Silva, D. G. J. Batista, E. M. De Souza, G. M. Oliveira, K. Salomão, M. M. Batista, M. G. O. Pacheco, P. B. Silva, R. M. Santa-Rita, R. F. S. Menna-Barreto, D. W. Boykin, and S. L. de Castro. 2009. Experimental chemotherapy for Chagas disease: 15 years of research contributions from in vivo and in vitro studies. Mem. Inst. Oswaldo Cruz 104(Suppl. I):301-310.
57. Soeiro, M. N. C., E. M. De Souza, and D. W. Boykin. 2007. Anti-parasitic activity of aromatic diamidines and theirs patented literature. Expert Opin. Patent Lit. 17:927-939.
58. Soeiro, M. N. C., E. M. De Souza, C. E. Stephens, and D. W. Boykin. 2005. Aromatic diamidines as antiparasitic agents. Expert Opin. Investig. Drugs 14:957-972.
59. Soeiro, M. N. C., S. L. De Castro, E. M. De Souza, D. G. J. Batista, C. F. Silva, and D. W. Boykin. 2008. Diamidine activity against trypanosomes: the State of the art. Curr. Mol. Pharmacol. 1:151-161.
60. Soeiro, M. N., and S. L. de Castro. 2009. Trypanosoma cruzi targets for new chemotherapeutic approaches. Expert Opin. Ther. Targets 13:105-121.
61. Sosa-Estani, S., R. Viotti, and E. L. Segura. 2009. Therapy, diagnosis and prognosis of chronic Chagas disease: insight gained in Argentina. Mem. Inst. Oswaldo Cruz 104(Suppl. I):167-180.
62. Souza, E. M., A. Henriques-Pons, C. Bailly, A. Lansiaux, T. C. Araújo-Jorge, and M. N. Soeiro. 2004. In vitro measurement of enzymatic markers as a tool to detect mouse cardiomyocytes injury. Mem. Inst. Oswaldo Cruz 99:697-701.
63. Souza, W. 2009. Structural organization of Trypanosoma cruzi. Mem. Inst. Oswaldo Cruz 104:89-100.
64. Stephens, C. E., F. Tanious, S. Kim, W. D. Wilson, W. A. Schell, J. R. Perfect, S. G. Franzblau, and D. W. Boykin. 2001. Diguanidino and "reversed" diamidino 2,5-diarylfurans as antimicrobial agents. J. Med. Chem. 44:1741-1748.
65. Susbielle, G., R. Blattes, V. Brevet, C. Monod, and E. Käs. 2005. Target practice: aiming at satellite repeats with DNA minor groove binders. Curr. Med. Chem. Anticancer Agents 5:409-420.
66. Teixeira, A. R., N. Nitz, M. C. Guimaro, C. Gomes, and C. A. Santos-Buch. 2006. Chagas disease. Postgrad. Med. J. 82:788-798.
67. Thuita, J. K., S. M. Karanja, T. Wenzler, R. E. Mdachi, J. M. Ngotho, J. M. Kagira, R. Tidwell, and R. Brun. 2008. Efficacy of the diamidine DB75 and its prodrug DB289, against murine models of human African trypanosomiasis. Acta Trop. 108:6-10.
68. Tidwell, R. R., S. K. Jones, J. D. Geratz, K. A. Ohemeng, M. Cory, and J. E. Hall. 1990. Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia. J. Med. Chem. 33:1252-1257.
69. Urbina, J. A. 2009. Ergosterol biosynthesis and drug development for Chagas disease. Mem. Inst. Oswaldo Cruz 104(Suppl. I):311-318.
70. Viotti, R., C. Vigliano, B. Lococo, G. Bertocchi, M. Petti, M. G. Alvarez, M. Postan, and A. Armenti. 2006. Long-term cardiac outcomes of treating chronic Chagas disease with benznidazole versus no treatment: a nonrandomized trial. Ann. Intern. Med. 144:724-734.
71. Wang, M. Z., X. Zhu, A. Srivastava, Q. Liu, J. M. Sweat, T. Pandharkar, C. E. Stephens, E. Riccio, T. Parman, M. Munde, S. Mandal, R. Madhubala, R. R. Tidwell, W. D. Wilson, D. W. Boykin, J. E. Hall, D. E. Kyle, and K. A. Werbovetz. 5 April 2010. Novel arylimidamides for the treatment of visceral leishmaniasis. Antimicrob. Agents Chemother. doi:10.1128/AAC.00250-10.
72. Wilson, W. D., F. A. Tanious, A. Mathis, D. Tevis, J. E. Hall, and D. W. Boykin. 2008. Antiparasitic compounds that target DNA. Biochimie 90:999-1014.
73. Wincker, P., C. Britto, J. B. Pereira, M. A. Cardoso, W. Oelemann, and C. M. Morel. 1994. Use of a simplified polymerase chain reaction procedure to detect Trypanosoma cruzi in blood samples from chronic chagasic patients in a rural endemic area. Am. J. Trop. Med. Hyg. 51:771-777.