6533b86efe1ef96bd12cc6e6
RESEARCH PRODUCT
Correlation of the Extent of Fjord-Region Oxidation with DNA Binding and Mutagenicity of the Enantiomeric 11,12-Dihydrodiols of Dibenzo[a,l]pyrene
Karl L. PlattFranz OeschHansruedi GlattAlbrecht SeidelAndreas Luchsubject
Polymers and PlasticsbiologyStereochemistryOrganic ChemistryAbsolute configurationSubstrate (chemistry)Epoxidebiology.organism_classificationChinese hamsterchemistry.chemical_compoundchemistrypolycyclic compoundsMaterials ChemistryMicrosomePyreneEnantiomerDNAdescription
Abstract In vitro studies on the hepatic biotransformation of the enantiomeric trans-11,12-dihydrodiols of dibenzo[a,l]pyrene (DB[a,l]P) using microsomal fractions of animals pretreated with Aroclor 1254 revealed that the formation of fjord-region dihydrodiol epoxides strongly depends on the absolute configuration of the substrate. Both the (-)-11R,12R- and the (+)-11S,12S-enantiomer are converted diastereoselectively to the (-)- and (+)-anti-dihydrodiol epoxide, respectively, by either rat or mouse liver microsomes. Fjord-region oxidation occurs to greatest extent on incubation of the (-)-11R,12R-dihydrodiol with preparations from rats. This finding is in line with the differences seen for the two enantiomers on the total DNA binding under identical activation conditions as well as on the mutagenic activity in Chinese hamster V79 cells using the postmitochondrial hepatic fraction of Aroclor 1254-treated rats as metabolizing system.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1996-11-01 | Polycyclic Aromatic Compounds |