Preparation, toxicity and mutagenicity of 1-methyl-2-nitrosoimidazole. A toxic 2-nitroimidazole reduction product.

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