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Journal of Spectroscopy and Dynamics 2013, 3: 8
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Research Article
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Indazoles and quinazolines as potential anti-Trypanosoma cruzi agents: An electrochemical, ESR and biological study
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Francisco Muraa, Hernán Speiskyb, Vicente J. Aránc, Juan D. Mayad, Claudio Olea-Azara, Benjamín Aguilera-Venegasa,b
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a Department of Inorganic and Analytical Chemistry, Faculty of Chemical and Pharmaceutical Sciences,
University of Chile, Sergio Livingstone 1007, Santiago, Chile
b Laboratory of Antioxidants, Institute of Nutrition and Food Technology, University of Chile, Av. Macul 5540,
Santiago, P. O. Box 138-11, Chile
c Instituto de Química Médica, Consejo Superior de Investigaciones Científicas,
Juan de la Cierva 3, 28006 Madrid, España
d Programa de Farmacología Molecular y Clínica, ICBM, Facultad de Medicina,
Universidad de Chile, Independencia 1027, Santiago, Chile
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Abstract |
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Electrochemical and ESR studies were carried out in this work with the purpose of characterizing the reduction mechanisms of a new series of nitroindazoles (NI) and nitroquinazolines (NQ) by means of cyclic voltammetry in DMSO as non-aqueous solvent. Two reduction mechanisms were found for these compounds: the first one, for compounds bearing labile hydrogens a self-protonation mechanism was observed. For compounds without labile hydrogen a purely electrochemical reduction mechanism was exhibited. The electrochemical results were corroborated by ESR spectroscopy, allowing us to propose the hyperfine splitting patterns of the nitro-radical, which was subsequently corroborated by the ESR simulation spectra. Additionally, all these compounds were assayed as growth inhibitors of Trypanosoma cruzi. Finally, in order to elucidate whether a free radical based-action mechanism is involved in the trypanocidal activity, spin trapping studies on T.cruzi microsomal fractions were also done.
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Keywords |
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Indazole; Quinazoline; ESR; Cyclic voltammetry; Antiprotozoal activity; Free radical; ROS production
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