Direct labeling of DNA-adducts formed from carcinogenic diol-epoxides with a fluorescent reporter compound specific for the cis vic-diol group.
The fluorescent reporter group, N-(5-FLUORESCEINYL),N'-(3-BORONATOPHENYL)THIOUREA (FABA) has been synthesized. This boronate group makes the reporter specific for cis vic-diols. The reporter group is bound to DNA-adducts formed from the reaction of calf-thymus DNA and benzanthracene trans-10,11-dihydrodiol,8,9-epoxide (anti), benzo(a)anthracene-trans-3,4-dihydrodiol-1,2-epoxide (anti) but is not bound to 3-methylcholanthrene-11,12 dihydro-epoxide. Femtomole quantities of adduct may be detected.
Uziel
M
M
Health and Safety Research Division, Oak Ridge National Laboratory, Tennessee 37831-6101.
Houck
K
K
D001551:Benz(a)Anthracenes / Q000737:chemistry / Q000378:metabolism*; D002273:Carcinogens / Q000378:metabolism*; D004247:DNA / Q000378:metabolism*; D005452:Fluoresceins / Q000138:chemical synthesis; D005456:Fluorescent Dyes; D008748:Methylcholanthrene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D013890:Thiourea / Q000031:analogs & derivatives / Q000138:chemical synthesis
D001551:Benz(a)Anthracenes; D002273:Carcinogens; D005452:Fluoresceins; D005456:Fluorescent Dyes; C071547:N-(5-fluoresceinyl)-N'-(3-boronatophenyl)thiourea; C017504:methylcholanthrene-11,12-epoxide; D008748:Methylcholanthrene; C071545:10,11-dihydrodiol-8,9-epoxide benzanthracene; C026832:3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(a)anthracene; D004247:DNA; D013890:Thiourea