Influence of amino acids on the formation of mutagenic/carcinogenic heterocyclic amines in a model system.
Mixtures of creatinine, glucose and various single amino acids were heated at 180 degrees C for 10 min in an aqueous model system. The heated mixtures all showed mutagenic activity, ranging from 80 to 2400 TA98 revertant colonies/mumol creatinine with metabolic activation. Testing of HPLC fractions for mutagenic activity showed each mixture to contain several mutagenic components, some of which corresponded to known heterocyclic amines and others to unknown compounds. The presence of 2-amino-3-methyl-imidazo[4,5-f]quinoxaline, 2-amino-3,8-dimethylmidazo[4,5-f]quinoxaline and 2-amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline in most of the samples was established using HPLC with photodiode array detection and liquid chromatography/mass spectrometry with electrospray interface and single ion monitoring. In addition, 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole and 3-amino-1-methyl-5H-pyrido[4,3-b]indole and the co-mutagenic compounds 9H-pyrido[3,4-b]indole and 1-methyl-9H-pyrido[3,4-b]indole were detected in some samples.
Johansson
M A
MA
Department of Applied Nutrition and Food Chemistry, Lund University, Sweden.
Fay
L B
LB
Gross
G A
GA
Olsson
K
K
Jägerstad
M
M
D000588:Amines / Q000494:pharmacology*; D000596:Amino Acids / Q000494:pharmacology*; D015197:Carcinogenicity Tests; D002273:Carcinogens / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D006571:Heterocyclic Compounds / Q000494:pharmacology*; D009152:Mutagenicity Tests; D009153:Mutagens / Q000494:pharmacology*; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
D000588:Amines; D000596:Amino Acids; D002273:Carcinogens; D006571:Heterocyclic Compounds; D009153:Mutagens