The binding of polycyclic aromatic hydrocarbon diol-epoxides to DNA.
Diol-epoxide derivatives of polycyclic aromatic hydrocarbons are the ultimate carcinogenic forms of these compounds encountered in vivo. Using a novel electro-fluorescence apparatus, we report that, like the (+/-)-anti-diol-epoxide of benzo[a]pyrene (BP), the similar diol-epoxides of benzo[a]anthracene (BA) and 3-methylcholanthrene (3MC) also bind to the DNA helix at an inclination of approximately 50 degrees. This compares with the essentially perpendicular, intercalative-type binding generally found with saturated aromatic compounds, such as the native hydrocarbons, and may indicate a systematic behavior in the molecular associations precursive to carcinogenesis.
D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D001551:Benz(a)Anthracenes / Q000378:metabolism* / Q000633:toxicity; D001580:Benzopyrenes / Q000378:metabolism; D002273:Carcinogens / Q000378:metabolism; D004247:DNA / Q000378:metabolism*; D004996:Ethidium / Q000378:metabolism; D005454:Fluorescence Polarization; D007536:Isomerism; D008748:Methylcholanthrene / Q000031:analogs & derivatives* / Q000378:metabolism / Q000633:toxicity
D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D002273:Carcinogens; D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D008748:Methylcholanthrene; C026832:3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(a)anthracene; C038099:9,10-dihydroxy-7,8-epoxy-7,8,9,10-tetrahydro-3-methylcholanthrene; D004247:DNA; C030935:benz(a)anthracene; D004996:Ethidium