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

doi:10.1016/0027-5107(91)90172-K

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 journal › Article › peer-review

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 language	English
Pages (from-to)	161-167
Number of pages	7
Journal	Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
Volume	250
Issue number	1-2
DOIs	https://doi.org/10.1016/0027-5107(91)90172-K
Publication status	Published - Jan 1 1991

Keywords

Heterocyclic amines
IQ
N-Nitrosodimethylamine
Near-ultraviolet light
Nitrosamines

ASJC Scopus subject areas

Molecular Biology
Genetics
Health, Toxicology and Mutagenesis

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Arimoto, S., & Hayatsu, H. (1991). 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. Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, 250(1-2), 161-167. https://doi.org/10.1016/0027-5107(91)90172-K

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. / Arimoto, Sakae; Hayatsu, Hikoya.

In: Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, Vol. 250, No. 1-2, 01.01.1991, p. 161-167.

Research output: Contribution to journal › Article › peer-review

Arimoto, S & Hayatsu, H 1991, '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', Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, vol. 250, no. 1-2, pp. 161-167. https://doi.org/10.1016/0027-5107(91)90172-K

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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",

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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.

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KW - Near-ultraviolet light

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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

Keywords

ASJC Scopus subject areas

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