Structure and mutagenicity of a direct-acting mutagen derived from the reaction of N-nitroso-N-methylbutylamine with hydroxyl radical

Keiko Inami, Motofumi Miura, Nozomi Tsutsumi, Eriko Okochi, Yoko Susaki, Satoko Ishikawa, Shigeyasu Motohashi, Junko Shiino, Kei Takeda, Masataka Mochizuki

研究成果: Article査読

2 被引用数 (Scopus)

抄録

The mutagenicity of N-nitrosamines is usually detected in the presence of an S9 mix, which includes cytochrome P450. The mutagenicity of N-nitrosodialkylamines is induced by Fe 2+-Cu 2+-H 2O 2, which can be used as a chemical model for cytochrome P450. However, a direct-acting mutagen derived from N-nitroso-N-methylbutylamine (NMB) by the same oxidation system has not been reported. In this study, we determined the structure of a direct-acting mutagen obtained from the reaction of NMB with Fe 2+-Cu 2+-H 2O 2 by comparing its instrumental data ( 1H, 13C NMR and IR) with that from the synthesized compound. We confirmed that the direct-acting mutagen derived from NMB with Fe 2+-Cu 2+-H 2O 2 was 5-methyl-5-nitro-1-pyrazoline 1-oxide. Furthermore, we investigated the mechanism of the mutagenicity by 5-methyl-5-nitro-1-pyrazoline 1-oxide using Salmonella typhimurium strains. The mutagenicity of 5-methyl-5-nitro-1- pyrazoline 1-oxide in S. typhimurium YG7108, which is deficient O 6-alkylguanine alkyltransferase, was higher than that in the parent strain S. typhimurium TA1535, indicating that the mutations are caused by DNA alkylation.

本文言語English
ページ(範囲)1081-1088
ページ数8
ジャーナルHeterocycles
84
2
DOI
出版ステータスPublished - 2012

ASJC Scopus subject areas

  • 分析化学
  • 薬理学
  • 有機化学

フィンガープリント

「Structure and mutagenicity of a direct-acting mutagen derived from the reaction of N-nitroso-N-methylbutylamine with hydroxyl radical」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル