title: Structural characteristics that determine the inhibitory role of phenolic compounds on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation.
abstract: In an attempt to understand the structural characteristics of phenolic compounds that favour the inhibition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation, this study analyzes the role of twenty-five phenolic compounds on the PhIP produced in phenylalanine/creatinine/oxidised lipid reaction mixtures. The results showed that phenols having two hydroxy groups at meta positions of the aromatic ring were the most efficient inhibitors. The presence of alkyl or carboxylic groups as additional substituents in the aromatic ring slightly reduced the inhibitory effect. On the other hand, the introduction of additional hydroxy and amino groups mostly cancelled the inhibitory effect, which was also mostly absent in ortho and para dihydroxy derivatives. In complex phenols, the presence of several rings with opposite effects produced a reduced inhibitory effect. All these results suggest that it is possible to predict if a phenolic derivative will inhibit the formation of PhIP, or not, based on its structure.
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Seville, Spain; Centro de Investigación y de Estudios Avanzados del I.P.N., Unidad Querétaro, Libramiento Norponiente # 2000, Fraccionamiento Real de Juriquilla, 76230 Juriquilla, Querétaro, Mexico.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Salazar
authors.affiliation: Centro de Investigación y de Estudios Avanzados del I.P.N., Unidad Querétaro, Libramiento Norponiente # 2000, Fraccionamiento Real de Juriquilla, 76230 Juriquilla, Querétaro, Mexico.
authors.forename: Gerónimo
authors.initials: G
authors.lastname: Arámbula-Villa
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Seville, Spain.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Hidalgo
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Seville, Spain. Electronic address: rzamora@ig.csic.es.
authors.forename: Rosario
authors.initials: R
authors.lastname: Zamora
mesh_terms: D002392:Catechin / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry; D015416:Maillard Reaction; D011794:Quercetin / Q000737:chemistry*; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D008055:Lipids; D013267:Stilbenes; D002392:Catechin; C049584:2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine; D011794:Quercetin; D000077185:Resveratrol
keywords: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine; Carbonyl-amine reactions; Catechin; EC50; Epicatechin; HAAs; Heterocyclic aromatic amines; IARC; International Agency for Research on Cancer; Maillard reaction; PhIP; Quercetin; Resorcinol; Resveratrol; heterocyclic aromatic amines; median effective concentration