Formation of PhIP in a mixture of creatinine, phenylalanine and sugar or aldehyde by aqueous heating.
A mixture of 100 mM creatinine and 100 mM L-phenylalanine was heated at 60 or 37 degrees C in the presence of sugar or aldehyde. A mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formed in the model system was determined by reversed-phase HPLC. Any sugars tested induced the formation of PhIP when heated at 60 degrees C, though PhIP was not detected in a mixture without sugar. Among the sugars tested, D-erythrose and D-glyceraldehyde were more productive than pentose (D-arabinose and D-ribose) and hexose (D-glucose and D-galactose) in the yield of PhIP. Moreover, PhIP was formed even when a mixture of creatinine, L-phenylalanine and D-glucose or D-ribose was incubated at 37 degrees C for a long time. Both formaldehyde and acetaldehyde also induced the formation of PhIP, though PhIP was not detected in a mixture without sugar or aldehyde even when heated at 100 degrees C. These results indicate that PhIP can be formed at low-temperature heating and that either sugar or aldehyde is essential for PhIP formation in the model system. Our data also suggest that aldehydes may be a key reactant in the formation of PhIP in aqueous heating of the mixture of creatinine and L-phenylalanine.
Manabe
S
S
Department of Hygiene and Preventive Medicine, Faculty of Medicine, University of Tokyo, Japan.
Kurihara
N
N
Wada
O
O
Tohyama
K
K
Aramaki
T
T
D000079:Acetaldehyde / Q000494:pharmacology*; D002241:Carbohydrates / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D003404:Creatinine; D005557:Formaldehyde / Q000494:pharmacology*; D006358:Hot Temperature; D007093:Imidazoles / Q000138:chemical synthesis*; D010649:Phenylalanine; D013696:Temperature; D013997:Time Factors
D002241:Carbohydrates; D007093:Imidazoles; D005557:Formaldehyde; D010649:Phenylalanine; C049584:2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine; D003404:Creatinine; D000079:Acetaldehyde