Identification of individual benzo[c]phenanthrene dihydrodiol epoxide-DNA adducts by the 32P-postlabeling assay.
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.
Canella
K A
KA
Chemistry of Carcinogenesis Laboratory, NCI-Frederick Cancer Research and Development Center, Maryland 21702.
Peltonen
K
K
Yagi
H
H
Jerina
D M
DM
Dipple
A
A
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
D004852:Epoxy Compounds; D009153:Mutagens; D010616:Phenanthrenes; C026153:benzo(c)phenanthrene 3,4-dihydrodiol; D004247:DNA