Mechanism of interaction of in situ produced nitroimidazole reduction derivatives with DNA using electrochemical DNA biosensor

Abstract

The electrochemical reduction of nitroimidazoles follows a complex mechanism and in theory the nitro group is able to receive up to six electrons to form the corresponding amine. Under anaerobic and low oxygen pressure conditions metronidazole follows a reduction mechanism similar to that of nitrobenzene. Electrochemical reduction of nitroimidazole derivatives shows two reduction waves in aqueous acid media, the first involving four electrons and corresponding to the reduction of the nitro group to form the intermediate hydroxylamine (-NHOH) and the second involving two electrons and corresponding to the reduction of the hydroxylamine to amine (-NH2). Using three different electrode materials (bare glassy carbon electrode, mercury thin film electrode, and DNA biosensor), it has been verified that hydroxylamine formation involves four electrons and is pH dependent. This chapter shows that the DNA biosensor developed provides a new perspective to the research and study of the mechanism of action of nitroimidazoles with DNA.