Formation of 2-nitro-3-methylimidazo[4,5-f]quinoline, a directly mutagenic product, by near-ultraviolet irradiation of a mixture of 2-amino-3-methylimidazo[4,5-f]quinoline and N-nitrosodimethylamine

Sakae Arimoto, Hikoya Hayatsu

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Direct-acting mutagens to Salmonella typhimurium TA98 were found to be formed from heterocyclic amines on exposure to near-ultraviolet light in the presence of N-nitrosodialkylamines. We have isolated the mutagenic photoproduct formed from 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and N-nitrosodimethylamine, and the product was identified as 3-methyl-2-nitromidazo[4,5-f]quinoline (IQ(NO2)). The yield of IQ(NO2) from IQ was estimated to be 17%. Similar light-dependent activation of IQ was noted with 4 different nitrosodialkylamines other than nitrosodimethylamine. Furthermore, MeIQ and MeIQx were also activated with nitrosamine and light. These reactions represent an example of interaction between 2 different classes of mutagens.

Original languageEnglish
Pages (from-to)161-167
Number of pages7
JournalMutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
Volume250
Issue number1-2
DOIs
Publication statusPublished - 1991

Fingerprint

2-amino-3-methylimidazo(4,5-f)quinoline
Dimethylnitrosamine
2-amino-3,4-dimethylimidazo(4,5-f)quinoline
Mutagens
Light
Nitrosamines
Salmonella typhimurium
Ultraviolet Rays
Amines
2-nitro-3-methylimidazo(4,5-f)quinoline

Keywords

  • Heterocyclic amines
  • IQ
  • N-Nitrosodimethylamine
  • Near-ultraviolet light
  • Nitrosamines

ASJC Scopus subject areas

  • Molecular Biology
  • Health, Toxicology and Mutagenesis

Cite this

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title = "Formation of 2-nitro-3-methylimidazo[4,5-f]quinoline, a directly mutagenic product, by near-ultraviolet irradiation of a mixture of 2-amino-3-methylimidazo[4,5-f]quinoline and N-nitrosodimethylamine",
abstract = "Direct-acting mutagens to Salmonella typhimurium TA98 were found to be formed from heterocyclic amines on exposure to near-ultraviolet light in the presence of N-nitrosodialkylamines. We have isolated the mutagenic photoproduct formed from 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and N-nitrosodimethylamine, and the product was identified as 3-methyl-2-nitromidazo[4,5-f]quinoline (IQ(NO2)). The yield of IQ(NO2) from IQ was estimated to be 17{\%}. Similar light-dependent activation of IQ was noted with 4 different nitrosodialkylamines other than nitrosodimethylamine. Furthermore, MeIQ and MeIQx were also activated with nitrosamine and light. These reactions represent an example of interaction between 2 different classes of mutagens.",
keywords = "Heterocyclic amines, IQ, N-Nitrosodimethylamine, Near-ultraviolet light, Nitrosamines",
author = "Sakae Arimoto and Hikoya Hayatsu",
year = "1991",
doi = "10.1016/0027-5107(91)90172-K",
language = "English",
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journal = "Mutation Research",
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TY - JOUR

T1 - Formation of 2-nitro-3-methylimidazo[4,5-f]quinoline, a directly mutagenic product, by near-ultraviolet irradiation of a mixture of 2-amino-3-methylimidazo[4,5-f]quinoline and N-nitrosodimethylamine

AU - Arimoto, Sakae

AU - Hayatsu, Hikoya

PY - 1991

Y1 - 1991

N2 - Direct-acting mutagens to Salmonella typhimurium TA98 were found to be formed from heterocyclic amines on exposure to near-ultraviolet light in the presence of N-nitrosodialkylamines. We have isolated the mutagenic photoproduct formed from 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and N-nitrosodimethylamine, and the product was identified as 3-methyl-2-nitromidazo[4,5-f]quinoline (IQ(NO2)). The yield of IQ(NO2) from IQ was estimated to be 17%. Similar light-dependent activation of IQ was noted with 4 different nitrosodialkylamines other than nitrosodimethylamine. Furthermore, MeIQ and MeIQx were also activated with nitrosamine and light. These reactions represent an example of interaction between 2 different classes of mutagens.

AB - Direct-acting mutagens to Salmonella typhimurium TA98 were found to be formed from heterocyclic amines on exposure to near-ultraviolet light in the presence of N-nitrosodialkylamines. We have isolated the mutagenic photoproduct formed from 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and N-nitrosodimethylamine, and the product was identified as 3-methyl-2-nitromidazo[4,5-f]quinoline (IQ(NO2)). The yield of IQ(NO2) from IQ was estimated to be 17%. Similar light-dependent activation of IQ was noted with 4 different nitrosodialkylamines other than nitrosodimethylamine. Furthermore, MeIQ and MeIQx were also activated with nitrosamine and light. These reactions represent an example of interaction between 2 different classes of mutagens.

KW - Heterocyclic amines

KW - IQ

KW - N-Nitrosodimethylamine

KW - Near-ultraviolet light

KW - Nitrosamines

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