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J.Health Sci., 56(5), 576-580, 2010
-Regular Article-
Oxidation Products of N-nitrosodialkylamines Generated by Fenton's Reagent in the Presence of Copper Are Direct Acting Mutagens
Keiko Inami,a, b Shiho Ishimura,a
Yuko Akaike,c Emako Suzuki,c
Nozomi Tsutsumi,a Kei Takeda,a
and Masataka Mochizuki*, a, b, c
aKyoritsu University of Pharmacy, Shibakoen 1-5-30, Minato-ku, Tokyo 105-8512, Japan,
bFaculty of Pharmaceutical Sciences, Tokyo University of Science, Yamazaki 2641, Noda 278-8510, Japan and
cTokyo Biochemical Research Institute, Takada 3-41-8, Toshima-ku, Tokyo 171-0033, Japan
N-Nitrosodialkylamines, activated metabolically by cytochrome P450, possess mutagenic and carcinogenic activity. In this study, the hydroxyl radical, generated from Fenton's 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 Fenton's reagent (Fe2+-H2O2) alone did not activate NMB, the addition of the copper ion to the reaction with Fenton's 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.
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