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PubMed1994

Dietary carcinogens and mammary carcinogenesis. Induction of rat mammary carcinomas by administration of heterocyclic amines in cooked foods.

Grilled or fried meat and fish contain various mutagenic heterocyclic amines, and structures of at least 19 compounds have already been determined. Among these, 10 have been examined for long term carcinogenicity, all proving to be positive. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), for example, preferentially induced mammary adenocarcinomas in 47% of Fischer 344 female rats when supplemented into the diet at a concentration of 400 parts per million (ppm) for 52 weeks. Moreover, 100 ppm of PhIP for 104 weeks yielded the same incidence. PhIP in the diet for 48 weeks also induced mammary cancer in Sprague-Dawley female rats with incidences of 72 and 25% at 200 ppm and 100 ppm. 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline in the diet at 300 ppm also induced a 25% incidence of mammary adenocarcinomas within 40 weeks. Analysis of PhIP-induced rat mammary carcinomas for ras mutations by polymerase chain reaction-single-strand conformation polymorphism and direct sequencing revealed Ha-ras activation in 3 of 17 carcinomas; all were G-->A transitions at the second letter of codon 12 replacing glycine by glutamic acid. A p53 gene mutation was also found in 1 of 10 carcinomas examined; a G-->T transversion was detected at the third letter of codon 130, with a substitution of asparagine for lysine. PhIP is the most abundant mutagenic and carcinogenic heterocyclic amine in grilled meat, and, therefore, a role for this compound in human carcinogenesis is strongly implied.

Adenocarcinoma↗
PubMed1993

Structural basis of the mutagenicity of heterocyclic amines formed during the cooking processes.

A data base consisting of 61 heterocyclic amines formed during food preparation and their des-amino 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).

Amines↗