Absolute configuration of 7,12-dimethylbenz[a]anthracene-DNA adducts in mouse epidermis.
32P-Postlabeling was used to monitor the formation of DMBA-DNA adducts in mouse epidermis from each enantiomer of the trans 3,4-dihydrodiol. It was shown that the (4R,3R)-dihydrodiol is converted to the anti (4R,3S)-dihydrodiol (2S,1R)-epoxide which reacts with deoxyguanosine and deoxyadenosine residues in epidermal DNA to yield two of the major adducts formed when DMBA itself binds to epidermal DNA. The third major DMBA-derived adduct with deoxyadenosine residues was shown to arise from the (4S,3R)-dihydrodiol through the intermediacy of the syn (4S,3R)-dihydrodiol (2S,1R)-epoxide.
Vericat
J A
JA
ABL-Basic Research Program, NCI-Frederick Cancer Research and Development Center, MD 21702.
Cheng
S C
SC
Dipple
A
A
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D002460:Cell Line; D004247:DNA / Q000737:chemistry*; D004249:DNA Damage; D004817:Epidermis / Q000378:metabolism; D004852:Epoxy Compounds; D066298:In Vitro Techniques; D051379:Mice; D010710:Phosphates; D013237:Stereoisomerism
D004852:Epoxy Compounds; D010710:Phosphates; D015127:9,10-Dimethyl-1,2-benzanthracene; D004247:DNA