Add time:07/23/2019         Source:sciencedirect.com

1-Methyl-2-nitrosoimidazole (INO), the 2-electron reduction product of 1-methyl-2-nitroimidazole (INO;), was prepared by electrochemical reduction of INO2 to 2-hydroxylamino-1-methylimidazole (INHOH), followed by back oxidation with iodine. Although stable in crystalline form, INO reacted in water, phosphate-buffered saline, and mammalian cell growth medium. Half-lives for decay were determined by UV-visible spectroscopy. INO was found to be highly toxic towards Chinese hamster ovary (CHO) cells, concentrations of 10–60 μM producing significant cytotoxicity. The rate of INO decay was found to be increased in the presence of CHO cells. INO was also toxic and mutagenic towards Salmonella typhimurium TA-100. When compared on a molar basis to the parent nitro compound INO2, and the 4- and 6-electron reduction products INHOH and 2-amino-1-methylimidazole (INH2), INO was by far (two orders of magnitude) the most toxic under aerobic conditions. These results suggest that the nitroso reduction product of 2-nitroimidazoles may be the reduced species responsible for hypoxic cell selective toxicity of 2-nitroimidazoles.

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