5-nitroimidazole compounds are an important class of antiamoebic, antiprotozoal, and antibacterial drugs. A major concern regarding the efficacy of these drugs is that some strains of microbes have evolved that are resistant to this treatment. It is widely accepted, that upon intracellular activation, the compound undergoes reduction to generate nitro radical anions. Evidence suggests a direct interaction between the activated intermediates and DNA bases that presumably leads to cell apoptosis. To understand further the mechanism of action, the structures of two nitroimidazole compounds were analyzed using both computational and analytical techniques. Theoretical analysis of metronidazole and ornidazole was performed using Gaussian and the results were compared to spectroscopic data. It was demonstrated that the calculations provided many correlations with experimental results. An ultimate goal of this project is to be able to understand the nature and the stability of the species formed upon activation such that new drug candidates can be designed.

Chemical and structural analysis of metronidazole and its derivatives

253rd National Meeting (2017)

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