title: Inhibition of 2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) Formation by Alkoxy Radical Scavenging of Flavonoids and Their Quantitative Structure-Activity Relationship in a Model System.
abstract: The inhibitory effect of 10 flavonoids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in a creatinine-phenylalanine model system was investigated through electronic spin resonance and a quantitative structure-activity relationship. Alkoxy radicals were observed during the heating process, providing evidence for a radical pathway in the formation of PhIP. The alkoxy radical scavenging capability of the flavonoids was proportional to their inhibition of PhIP formation (IC50 ). We deduced that flavonoid inhibition of PhIP generation occurs via scavenging of alkoxy radicals during the heating process. Multiple linear regression and partial least squares models were used to elucidate the relationship between PhIP inhibition activity and structure characteristics of the flavonoids. The lipo-hydro partition coefficient and molecular fractional polar surface area of the flavonoids were found to be predictive of the inhibition effect.
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education of China, Tianjin Univ. of Science and Technology, Tianjin, 300457, China.|College of Food Science and Engineering, Qingdao Agricultural Univ, Qingdao, 266109, China.
authors.forename: Chundi
authors.initials: C
authors.lastname: Yu
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education of China, Tianjin Univ. of Science and Technology, Tianjin, 300457, China.
authors.forename: Zeping
authors.initials: Z
authors.lastname: Shao
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education of China, Tianjin Univ. of Science and Technology, Tianjin, 300457, China.
authors.forename: Bing
authors.initials: B
authors.lastname: Liu
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education of China, Tianjin Univ. of Science and Technology, Tianjin, 300457, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education of China, Tianjin Univ. of Science and Technology, Tianjin, 300457, China.
authors.forename: Shuo
authors.initials: S
authors.lastname: Wang
mesh_terms: D000438:Alcohols / Q000378:metabolism*; D000818:Animals; D002273:Carcinogens / Q000378:metabolism*; D003404:Creatinine / Q000378:metabolism; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D005609:Free Radicals / Q000378:metabolism*; D006571:Heterocyclic Compounds / Q000378:metabolism; D007093:Imidazoles / Q000378:metabolism*; D008954:Models, Biological; D010649:Phenylalanine / Q000378:metabolism; D010936:Plant Extracts / Q000494:pharmacology*; D011725:Pyridines / Q000378:metabolism; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000438:Alcohols; D002273:Carcinogens; D005419:Flavonoids; D005609:Free Radicals; D006571:Heterocyclic Compounds; D007093:Imidazoles; D010936:Plant Extracts; D011725:Pyridines; C059688:alkoxyl radical; D010649:Phenylalanine; C049584:2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine; D003404:Creatinine; C023666:pyridine
keywords: PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine); alkoxy radical; flavonoids; quantitative structure-activity relationship