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Evidence-Based Complementary and Alternative Medicine
Volume 2013, Article ID 945953, 10 pages
Research Article

Trypanocidal Activity of Thioamide-Substituted Imidazoquinolinone: Electrochemical Properties and Biological Effects

1Departamento de Microbiología, Facultad de Medicina, IMPaM (UBA-CONICET) and Cátedra de Inmunología, Facultad de Farmacia y Bioquímica, UBA, Paraguay 2155 P13, 1121 Buenos Aires, Argentina
2Centro de Investigaciones Sobre Porfirinas y Porfirias, CIPYP (UBA-CONICET), Hospital de Clínicas José de San Martín, UBA, Córdoba 2351, 1120 Buenos Aires, Argentina
3Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, UBA, Junín 956, 1113 Buenos Aires, Argentina
4Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, 2° Piso CM1, UBA, Int. Güiraldes 2160, CABA, 1428 Buenos Aires, Argentina

Received 25 February 2013; Accepted 30 May 2013

Academic Editor: Roser Vila

Copyright © 2013 Fernanda M. Frank et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Three thioamide-substituted imidazoquinolinone, which possess a heterocyclic center similar to tryptanthrin and are named C1, C2, and C3, were studied regarding (a) their in vitro anti-Trypanosoma cruzi activity, (b) their cytotoxicity and electrochemical behaviour, and (c) their effect on cell viability, redox state, and mitochondrial function. The assayed compounds showed a significant activity against the proliferative forms, but only C1 showed activity on the trypomastigote form (for C1, ?; ?; and ?). The presence of an antioxidant compound such as ascorbic acid or dithiotreitol induced a threefold increase in the antiparasitic activity, whereas glutathione had a dual effect depending on its concentration. Our results indicate that these compounds, which exhibited low toxicity to the host cells, can be reduced inside the parasite by means of the pool of low molecular weight thiols, causing oxidative stress and parasite death by apoptosis. The antiparasitic activity of the compounds studied could be explained by a loss of the capacity of the antioxidant defense system of the parasite to keep its intracellular redox state. C1 could be considered a good candidate for in vivo evaluation.