Nitroimidazoles are biologically active compounds that also have medicinal uses. 5-Nitroimidazoles are currently used as anti-bacterial drugs and a 2-nitroimidazole is used to treat Chagas disease. The nitroso and hydroxylamine, which are reduced forms of nitroimidazoles, are believed to be the active anti-bacterial agents. Compared to the 2- and 5-nitroimidazoles, 4-nitroimidazoles are known to be inactive under biological conditions. In this project cyclic voltammetric analysis of a simple 4-nitroimidazole, 1-methyl-4-nitroimidazole, is currently being run to analyze the stability of its reduction products under biological conditions and their reactivity with cysteine. Previous studies of the 4-nitroimidazole have been done in DMSO with cysteine additions because it is believed that the reaction of nitroimidazole with cysteine is the likely cause of cell death in bacterial species. The cyclic voltammetric analysis between the 2-, 4-, and 5-nitroimidazoles in DMSO with cysteine additions yielded similar trends of reduction and oxidation potential. Between the 4- and the 5-nitroimidazoles, the 4-nitroimidazole is shown to have a more negative reduction potential than the 5-nitroimidazole. This difference in reduction potential might be the cause of the 4-nitroimidazole inactivity under biological conditions. Currently the 4-nitroimidazole is being analyzed under aqueous conditions with cysteine additions. This change from DMSO to an aqueous solution allows for further analysis of the compound under biological conditions.

Cyclic voltammetric analysis of 1-methyl-4-nitroimidazole under biological conditions

251st National Meeting (2016)

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