title: Identification of individual benzo[c]phenanthrene dihydrodiol epoxide-DNA adducts by the 32P-postlabeling assay.
abstract: Purine deoxyribonucleoside 3'-phosphates were reacted separately with the four configurational isomers of benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide. Products resulting from the cis and trans opening of the epoxide ring by the exocyclic amino groups of deoxyadenosine and deoxyguanosine 3'-phosphates were separated by high-pressure liquid chromatography and identified by comparison of the observed circular dichroism spectra with the known spectra for the corresponding nucleoside adducts. The 16 structurally identified benzo[c]phenanthrene-purine deoxyribonucleoside 3'-phosphate adducts were then separately postlabeled according to the Randerath method, and the positions of the individual bisphosphates were mapped by thin-layer chromatography. Chromatographic conditions were developed that allowed separation of the four adducts for 3 of the 4 dihydrodiol epoxide isomers.
authors.affiliation: Chemistry of Carcinogenesis Laboratory, NCI-Frederick Cancer Research and Development Center, Maryland 21702.
authors.forename: K A
authors.initials: KA
authors.lastname: Canella
authors.forename: K
authors.initials: K
authors.lastname: Peltonen
authors.forename: H
authors.initials: H
authors.lastname: Yagi
authors.forename: D M
authors.initials: DM
authors.lastname: Jerina
authors.forename: A
authors.initials: A
authors.lastname: Dipple
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D009153:Mutagens / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D009153:Mutagens; D010616:Phenanthrenes; C026153:benzo(c)phenanthrene 3,4-dihydrodiol; D004247:DNA