Mutagenesis Advance Access originally published online on October 9, 2006
Mutagenesis 2006 21(6):399-404; doi:10.1093/mutage/gel045
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Mutagenic activities and physicochemical properties of selected nitrobenzanthrones
1 Department of Applied Chemistry, Kanagawa Institute of Technology 1030 Shimo-Ogino, Atsugi-shi 243-0292, Japan 2 Department of Chemistry, Graduate School of Science, Kyoto University Sakyo-ku, Kyoto 606-8502, Japan 3 Department of Community Environmental Science, National Institute of Public Health 2-3-6 Minami, Wako-shi, Saitama 351-0197, Japan
Mutagenic activity of nine nitro derivatives of benzanthrone, namely 1-nitro-, 2-nitro-, 3-nitro-, 9-nitro-, 11-nitro-, 1,9-dinitro-, 3,9-dinitro-, 3,11-dinitro- and 3,9,11-trinitrobenzanthrone were tested with Salmonella strains TA98, TA100, YG1021 and YG1024 in both the presence and absence of an S9 mix. Each compound exhibited mutagenic activity with all the strains. Among these nine isomers, 3-nitrobenzantrone exhibited the most mutagenic activity with all the strains without the S9 mix. The mutagenic activities of the dinitro and trinitro derivatives of benzanthrone were lower than that of the 3-nitro derivative; this is evident from the mutagenic activity of nitrated polyaromatic hydrocarbons (PAH), which is generally enhanced with an increase in nitration. The physicochemical properties of nitrated benzanthrone (reduction potential, hydrophobicity and orientation of nitro groups to the aromatic ring) demonstrated that mononitrated benzanthrone exhibits a lower reduction potential than mononitroPAHs such as 1-nitropyrene and 3-nitrofluoranthene, but was almost equivalent to that of dinitroPAH. Moreover, the mutagenic activity of mononitrobenzanthrones clearly depend on the reduction potential of each compound; however, this tendency was not observed in polynitrobenzanthrones, probably because the reduction of the nitro groups to amino groups of polynitrated benzanthrone might be predominant without a sufficient formation of corresponding hydroxyamines. These results suggest that aromatic compounds that contain keto groups, when nitrated, may act as potentially powerful direct-acting mutagens.
#Present address: Tokyo University of Agriculture and Technology, Field Science Center, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo 183-8509, Japan
*To whom correspondence should be addressed. Tel: +81 46 291 3072; Fax: +81 46 242 8760; Email: takamura{at}chem.kanagawa-it.ac.jp
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