Activation Mechanism of 2-Acetylamino-9-fluorenone as a Mutagen in Salmonella typhimurium

• Inami Keiko

  Kyoritsu University of Pharmacy

• Mochizuki Masataka

  Kyoritsu University of Pharmacy

抄録

2-Acetylaminofluorene (AAF) is a procarcinogen and its activation mechanisms have been investigated in detail. AAF was metabolized to 2-acetylamino-9-fluorenone (AAF=O) and 2-acetylamino-9-fluorenol by S9 mix. The mutagenicity of AAF=O in the presence of S9 mix was equal in potency to that of AAF in Salmonella typhimurium TA1538, but the activation mechanism of AAF=O was poorly reported. In this study, we investigated possible ultimate species derived from AAF=O; N-hydroxy-2-acetylamino-9-fluorenone (N-OH-AAF=O), N-acetoxy-2-acetylamino-9-fluorenone (N-OAc-AAF=O), N-hydroxy-2-amino-9-fluorenone (N-OH-AF=O), and N-acetoxy-2-trifluoroacetylamino-9-fluorenone (N-OAc-TFAAF=O), a model compound for N-acetoxy-2-amino-9-fluorenone (N-OAc-AF=O), were synthesized and their mutagenicity was examined in S. typhimurium TA1538. The activation mechanism in S. typhimurium TA1538 was also investigated. The compounds in order of decreasing mutagenicity are N-OAc-TFAAF=O>N-OH-AF=O>N-OAc-AAF=O> N-OH-AAF=O. AAF=O is at least partially responsible for the mutagenicity of AAF, since a small amount of AAF is oxidized to AAF=O in the presence of S9 mix. Furthermore we suggest that an ultimate active species of AAF=O in S. typhimurium is N-OAc-AF=O, with the same activation manner as AAF.<br>

収録刊行物

• Genes and Environment

  Genes and Environment 30 (3), 71-76, 2008

  日本環境変異原学会

キーワード

• 2-acetylamino-9-fluorenone
• 2-acetylaminofluorene
• metabolic activation

詳細情報

• CRID: 1390282680233694976
• NII論文ID: 110006873843
• NII書誌ID: AA1212552X
• DOI: 10.3123/jemsge.30.71
• ISSN: 18807062
• ISSN: 18807046
• NDL書誌ID: 9628222
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9628222
• Web Site: https://search.jamas.or.jp/link/ui/2008367527
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可