Correlations between chemical reactivity and mutagenic activity against S. typhimurium TA100 for alpha-dicarbonyl compounds as a proof of the mutagenic mechanism.
The mutagenic activities in the Ames test against S. typhimurium TA100 for a series of alpha-dicarbonyl compounds are examined together with the formation constants of the adducts formed between such compounds and guanine and guanosine. Correlations between the equilibrium constants, the apparent reaction enthalpies, and the mutagenic activity are presented. These correlations imply that the mutagenic activity is related to the chemical reactivity of the dicarbonyl compounds with the puric bases.
Rodríguez Mellado
J M
JM
Departamento de Química Física y Termodinámica Aplicada, Facultad de Ciencias, Universidad de Córdoba, Spain.
Ruiz Montoya
M
M
D000447:Aldehydes / Q000737:chemistry* / Q000494:pharmacology; D003512:Cyclohexanones / Q000737:chemistry / Q000494:pharmacology; D004249:DNA Damage; D003931:Diacetyl / Q000737:chemistry / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D006037:Glyoxal / Q000737:chemistry / Q000494:pharmacology; D006147:Guanine / Q000737:chemistry; D006151:Guanosine / Q000737:chemistry; D006588:Hexanones / Q000737:chemistry / Q000494:pharmacology; D016296:Mutagenesis; D009152:Mutagenicity Tests / Q000379:methods; D009153:Mutagens / Q000737:chemistry* / Q000494:pharmacology; D010658:Phenylglyoxal / Q000737:chemistry / Q000494:pharmacology; D011765:Pyruvaldehyde / Q000737:chemistry / Q000494:pharmacology; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D000447:Aldehydes; D003512:Cyclohexanones; D006588:Hexanones; D009153:Mutagens; D006151:Guanosine; D006037:Glyoxal; D006147:Guanine; D011765:Pyruvaldehyde; C018031:1,2-cyclohexanedione; D003931:Diacetyl; D010658:Phenylglyoxal