A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100
- 1 January 1992
- journal article
- research article
- Published by Wiley in Environmental and Molecular Mutagenesis
- Vol. 19 (1), 37-52
- https://doi.org/10.1002/em.2850190107
Abstract
Quantitative structure-activity relationships (QSAR) have been derived for the mutagenic activity of 88 aromatic and heteroaromatic amines acting on Salmonella typhimurium TA98 + S9 and 67 amines acting on TA100 + S9. Mutagenic activity is linearly dependent on hydrophobicity, the energy of the highest occupied molecular orbital, and the energy of the lowest unoccupied molecular orbital of the amine. The dependence of mutagenic activity on hydrophobicity and electronic effects is nearly identical for TA98 and TA100. Mutagenic activity in TA98 is also found to depend on the size of the aromatic ring system. Different QSARs are derived for the mutagenic activity of hydrophilic amines (log P < 1) acting on either TA98 or TA100. The mechanism of amine activation and reaction with DNA is considered in light of these findings.Keywords
This publication has 38 references indexed in Scilit:
- LUMO Energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds inSalmonella typhimuriumEnvironmental and Molecular Mutagenesis, 1990
- Mutagenicity of nitro- and amino-substituted phenazines in Salmonella typhimuriumMutation Research Letters, 1989
- Relationships among direct-acting mutagenicity, nitro group orientation and polarographic reduction potential of 6-nitrobenzo[a]pyrene, 7-nitrobenz[a]anthracene and their derivativesMutation Research Letters, 1988
- The orientation of the nitro substituent predicts the direct-acting bacterial mutagenicity of nitrated polycyclic aromatic hydrocarbonsMutation Research Letters, 1985
- Relationship between mutagenic potency in Salmonella typhimurium and chemical structure of amino- and nitro-substituted biphenylsMutation Research, 1985
- Computer analysis of toxicological data bases: Mutagenicity of aromatic amines in Salmonella tester strainsEnvironmental Mutagenesis, 1985
- Metabolism of 1,8-dinitropyrene by Salmonella typhimuriumChemico-Biological Interactions, 1984
- Microbial mutagenicity of isomeric two‐, three‐, and four‐ring amino polycyclic aromatic hydrocarbonsEnvironmental Mutagenesis, 1984
- Esterification of arylhydroxylamines: Evidence for a specific gene product in mutagenesisBiochemical and Biophysical Research Communications, 1982