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Structural basis of the mutagenicity of heterocyclic amines formed during the cooking processes
Author(s) -
Zhang Ying Ping,
Klopman Gilles,
Rosenkranz Herbert S.
Publication year - 1993
Publication title -
environmental and molecular mutagenesis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1
H-Index - 87
eISSN - 1098-2280
pISSN - 0893-6692
DOI - 10.1002/em.2850210114
Subject(s) - moiety , homo/lumo , chemistry , potency , structure–activity relationship , molecule , structural isomer , molecular orbital , computational chemistry , heterocyclic compound , quantitative structure–activity relationship , molecular descriptor , quantum chemical , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , in vitro
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.) © 1993 Wiley‐Liss, Inc.