Electrochemical Reduction Using Glassy Carbon Electrode in Aqueous Medium of a Potential Anti-Chagas Drug: NFOH

Autor(es)

La-Scalea, M. A. ^{[1, 2]} ; Trossini, G. H. G. ^[1] ; Menezes, C. M. S. ^{[1, 3]} ; Chung, M. C. ^[4] ; Ferreira, E. I. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo - Brazil

^[2] Univ Fed Sao Paulo, Dept Ciencias Exactas & Terra, Diadema - Brazil

^[3] Univ Fed Rio de Janeiro, LaSSBio, Fac Farm, Rio De Janeiro - Brazil

^[4] Univ Estadual Julio de Mesquita Filho, Dept Farmacos & Medicamentos, Fac Ciencias Farmaceut, Araraquara - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Electrochemical Society; v. 156, n. 7, p. F93-F97, 2009.
• Citações Web of Science: 8

Resumo

Nitrofurazone (NF) presents activity against Chagas' disease, yet it has a high toxicity. Its analog, hydroxymethylnitrofurazone (NFOH), is more potent against Trypanosoma cruzi and much less toxic than the parent drug, NF. The electrochemical reduction of NFOH in an aqueous medium using a glassy carbon electrode (GCE) is presented. By cyclic voltammetry in anacidic medium, one irreversible reduction peak related to hydroxylamine derivative formation was registered, being linearly pH dependent. However, from pH > 7, a reversible reduction peak at a more positive potential appears and corresponds to the formation of a nitro radical anion. The radical-anion kinetic stability was evaluated by Ip(a)/Ip(c) the current ratio of the R-NO(2)/R-NO(2)-redox couple. The nitro radical anion decays with a second-order rate constant (k(2)) of 6.07, 2.06, and 1.44(X 10(3)) L mol(-1) s(-1) corresponding to pH 8.29, 9.29, and 10.2, respectively, with a corresponding half-time life (t(1/2)) of 0.33, 0.97, and 1.4 s for each pH value. By polishing the GCE surface with diamond powder and comparing with the GCE surface polished with alumina, it is shown that the presence of alumina affects the lifetime of the nitro radical anion. (C) 2009 The Electrochemical Society. {[}DOI: 10.1149/1.3130082] All rights reserved. (AU)

• Processo FAPESP: 01/09418-0 - Estudo do comportamento voltamétrico de nitro-heterocíclicos com atividade antichagásica
• Beneficiário: Mauro Aquiles La Scalea
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado
• Processo FAPESP: 01/01192-3 - Antichagásicos potenciais derivados de compostos nitro-heterocíclicos
• Beneficiário: Elizabeth Igne Ferreira
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 03/10763-0 - Estudos de compostos nitro-heterocíclicos potencialmente antichagásicos
• Beneficiário: Mauro Aquiles La Scalea
• Modalidade de apoio: Auxílio à Pesquisa - Programa Primeiros Projetos