MUTAGENIC AND DNA-DAMAGING EFFECTS OF N-ALKYL-N-(α-ACETOXYALKYL) NITROSAMINES, MODELS FOR METABOLICALLY ACTIVATED N, N-DIALKYLNITROSAMINES
Mutagenic and DNA-damaging effects of a series of N, N-dialkylnitrosamines monosubstituted at the α-carbon with an acetoxyl group were tested in Salmonella typhimurium, Escherichia coli, and Bacillus subtilis in the absence of metabolic activation system. The compounds comprised 8 N-alkyl-N-(acetoxy...
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Published in | GANN Japanese Journal of Cancer Research Vol. 70; no. 5; pp. 663 - 670 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Japan
The Japanese Cancer Association
01.01.1979
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Subjects | |
Online Access | Get full text |
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Summary: | Mutagenic and DNA-damaging effects of a series of N, N-dialkylnitrosamines monosubstituted at the α-carbon with an acetoxyl group were tested in Salmonella typhimurium, Escherichia coli, and Bacillus subtilis in the absence of metabolic activation system. The compounds comprised 8 N-alkyl-N-(acetoxymethyl)nitrosamines (alkyl=methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, or tert-butyl) and N-butyl-N-(1-acetoxybutyl)nitrosamnie. All the compounds, except one with a tert-butyl group, gave positive results in these mutagenicity and repair tests. Presumed release of alkyl cations from the corresponding α-acetoxy derivatives by hydrolysis and heterolysis caused mutagenic and DNA-damaging effects in the bacteria. Structure-activity correlation of the compounds was noted in these tests and discussed in regard to the mutagenicity with metabolic activation and carcinogenicity of N, N-dialkylnitrosamines. The results support the hypothesis that α-carbon hydroxylation is one probable mechanism involved in the metabolic activation of N, N-dialkylnitrosamines. |
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ISSN: | 0016-450X |
DOI: | 10.20772/cancersci1959.70.5_663 |