Structural basis of the mutagenicity of heterocyclic amines formed during the cooking processes
- 1 January 1993
- journal article
- Published by Wiley in Environmental and Molecular Mutagenesis
- Vol. 21 (1), 100-115
- https://doi.org/10.1002/em.2850210114
Abstract
A data base consisting of 61 heterocyclic amines formed during food preparation and their desamino analogs were subjected to structure‐activity analysis using the CASE method, a structural activity relational expert system. The program identified the major structural determinants associated with mutagenic activity or lack thereof. The structures identified as contributing to the probability of activity as well as those associated with mutagenic potency were highly predictive of molecules not in the learning set. The major structural determinant, the aromatic amino moiety, and quantum mechanical calculations revealed that the mutagenic potency associated with this functionality derived from their contribution to the energy of the Lowest Unoccupied Molecular Orbital (LUMO.)Keywords
This publication has 19 references indexed in Scilit:
- Structure-activity relations: maximizing the usefulness of mutagenicity and carcinogenicity databases.Environmental Health Perspectives, 1991
- Structure activity-based predictive toxicology: an efficient and economical method for generating non-congeneric data basesMutagenesis, 1991
- Quantitative structure‐activity relationships of heterocyclic amine mutagens formed during the cooking of foodEnvironmental and Molecular Mutagenesis, 1991
- The structural basis of the mutagenicity of chemicals in Salmonella typhimurium: The Gene-Tox Data BaseMutation Research - Reviews in Mutation Research, 1990
- Carcinogenicity of 2‐Amino‐3‐methylimidazo[4,5‐f]quinoline in Nonhuman Primates: Induction of Tumors in Three MacaquesJapanese Journal of Cancer Research, 1990
- A new tool for the rapid estimation of charge distributionJournal of Computational Chemistry, 1988
- Activated N-ras oncogene in a transformant derived from a rat small intestinal adenocarcinoma induced by 2-aminodipyrido[1,2-a:3',2'-d]imidazoleCarcinogenesis: Integrative Cancer Research, 1987
- Metabolic aspects of pyrolysis mutagens in food.Environmental Health Perspectives, 1986
- Epidemiologic studies on possible health effects of intake of pyrolyzates of foods, with reference to mortality among Japanese Seventh-Day Adventists.Environmental Health Perspectives, 1986
- Metabolic Aspects of Pyrolysis Mutagens in FoodEnvironmental Health Perspectives, 1986