Micellar Effects on the Reduction of 4‐Nitroimidazole Derivative: Detection and Quantification of the Nitroradical Anion

Abstract

The reductive electrochemistry of 1-methyl-4-nitro-2-hydroxymethylimidazole, a 4-nitroimidazole derivative, was examined in the presence of surfactants anionic as sodium dodecyl sulfate (SDS), nonionic, Triton-X, Cationic, Hyamine and Cetyl Trimethyl Ammonium Bromide (CTAB). The reductive mechanism of the nitroimidazole derivative was found to be dependent of both, nature and concentration of the surfactants. By using appropriately the wide versatility of the cyclic voltammetric technique it was possible to study the generation of the nitroradical anion and their stability in different micellar media. The experimental scheme involved the measurement of the current ratio, i p, a /i p, c , from the cyclic voltammograms and its interpolation into theoretical working curves to determine the w parameter. A plot of w versus t resulted in a linear relation described by w ¼ k 2 C t where k 2 is the second order rate constant for the decomposition of the nitroradical anion. Cyclic voltammetric experiments demonstrated that the reduction of the 4-nitroimidazole derivative in presence of cationic micelles generated a sufficiently well stabilized nitroradical anion in aqueous medium at pH 7.4. The aim of this study is to investigate the electrochemistry of 4-MNImOH in a micellar medium with the objective to obtain a better approach to the in-vivo conditions and to improve the detection and quantification of the nitroradical anion species.

Voltammetric Reduction of a 4‐Nitroimidazole Derivative on a Multiwalled Carbon Nanotubes Modified Glassy Carbon Electrode

“…At pH above pH 7 the slope changes because the mechanism changes to a different situation wherein there are no protons involved before the rate determining step. A similar pH-dependence was obtained from a different electrode as Hg [13]. From this similarity is clear that the voltammetric behavior of 4-NImMeOH follows the same overall mechanism on MWCNT modified GCE than mercury.…”

“…However, electrochemical studies of 4-nitroimidazole derivatives are scarce and restricted to a polarographic study of several 1,2-dialkyl-4nitroimidazoles [9] and some electrochemical studies about the cyclic voltammetric behavior of 4-nitroimidazole in aprotic [10] and protic media [11]. Furthermore, in a previous paper [12], we studied the nitro radical anion formation from a new 4-nitroimidazole derivative and more recently the micellar effects on the reduction of the same 4nitroimidazole derivative was also evaluated [13].…”

Development of Electro-Analytical Methods Using Electrochemical Carbon-Based Sensors for Determination of Trifloxystrobin, Gentamicin and Lapachol

“…Surfactants might influence redox processes and minimize the passivation of the electrode surface caused by adsorption of electrogenerated products or by sample matrix components [179,180]. In addition, they improve the solubility of more hydrophobic analytes and facilitate mass transport [181,182].…”