Oxidation Products of N-nitrosodialkylamines Generated by Fentons Reagent in the Presence of Copper Are Direct Acting Mutagens

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N-Nitrosodialkylamines, activated metabolically by cytochrome P450, possess mutagenic and carcinogenic activity. In this study, the hydroxyl radical, generated from Fentons reagent, was used as an oxidant for the activation of the N-nitrosodialkylamines. Ethyl acetate extract from the reaction mixture which included Fe2+-Cu2+-H2O2 and N-nitrosodialkylamines; N-nitrosodimethylamine (NDM), N-nitrosodiethylamine (NDE), N-nitrosodipropylamine (NDP), N-nitrosodibutylamine (NDB), N-nitroso-N-methylpropylamine (NMP), N-nitroso-N-methylbutylamine (NMB), were assayed for their mutagenicity in Salmonella typhimurium (S. typhimurium) TA1535 and Escherichia coli (E. coli) WP2 uvrA. Although Fentons reagent (Fe2+-H2O2) alone did not activate NMB, the addition of the copper ion to the reaction with Fentons reagent (Fe2+-Cu2+-H2O2) resulted in the production of mutagens. While the extracts of the reaction of NDM or NDE with Fe2+-Cu2+-H2O2 were not mutagenic, those of NMP, NDP, NMB, or NDB with Fe2+-Cu2+-H2O2 were mutagenic in both S. typhimurium TA1535 and E. coli WP2 uvrA. These results demonstrate that a direct-acting mutagen was formed from N-nitrosodialkylamines, with alkyl chains longer than propyl, by the oxidation in the Fe2+-Cu2+-H2O2 system.