Mutagenicity of Quinoline Derivatives and Analogs—Quinoxaline 1,4-Dioxide is a Potent Mutagen

Teruko Hashimoto, Tomoe Negishi, Tetsuto Namba, Shohei Hayakawa, Hikoya Hayatsu

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)


Quinoline derivatives and analogs were surveyed for their mutagenicity using the Salmonella/microsome assay. 4-Methylquinoline, 4-methylquinoline 1-oxide, quinoxaline 1-oxide, quinoxaline 1,4-dioxide, 2,3-dimethylquinoxaline 1,4-dioxide, benzo[f]quinoline, l-methylbenzo[f] quinoline, and 4-methylbenzo[h]quinoline were mutagenic on S. typhimu-rium TA 100 in the presence of the rat liver 9000 Xg supernatant (“S-9 mix”). Quinoxaline 1- oxide, quinoxaline 1,4-dioxide, and 2,3-dimethylquinoxaline 1,4-dioxide were also mutagenic on TA 100 in the absence of S-9 mix. 2-Methylquinoxaline was mutagenic on strain TA 98 in the presence of S-9 mix. Among these mutagenic compounds, quinoxaline 1,4-dioxide was the strongest mutagen. The following compounds showed no significant mutagenicity on TA 98 and TA 100 both in the presence and absence of S-9 mix: 2- methylquinoline, 2,4-dimethylquinoline, quinoline-2-carboxamide, 4-methylquinoline-2-carboxamide, N-methylquinoline-2-carboxamide, N,4-dimethylquinoline-2-carboxamide, 2-(2-pyrazinyl)quinoline, 2-(5-pyrimidinyl)quinoline, benzo[h] quinoline, 1,10-phenanthroline, quinoline 1-oxide, 2-methylquinoline 1-oxide, 2,4-dimethylquinoline 1-oxide, isoquinoline, 3-methylisoquinoline, isoquinoline-1-carboxamide, 4-chloroquinazoline, quinoxaline, 2,3-dimethylquinoxaline, 3-methylquinoxaline-2-carboxamide, 2,3-bis(2-pyridyl)-quinoxaline and acridine.

Original languageEnglish
Pages (from-to)1954-1956
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Issue number8
Publication statusPublished - May 1979


  • S-9
  • Salmonella typhimurium TA 98 100
  • metabolic activation
  • mutagenicity
  • quinoline analogs
  • quinoline derivatives
  • quinoxaline 1,4-dioxide

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery


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