Electrofluorescence study of polycyclic hydrocarbon diol-epoxide binding to DNA.
By the use of a novel electrofluorescence method, estimates have been made of the geometry of binding to DNA of racemic mixtures of the anti-diol-epoxide derivatives of three polycyclic hydrocarbon carcinogens. These anti-configurations bind in a manner consistent with the planar diol-epoxide ring's being inclined at approximately 50 degrees to the DNA axis. This is true for the derivatives of benzo(a)pyrene, benz(a)anthracene and 3-methylcholanthrene. This binding is thus different from the regular intercalative interaction associated with the native hydrocarbons. As the (+ anti)-diol-epoxides are thought to be the initiatory compounds for carcinogenesis, the common binding characteristics for the three hydrocarbons may be significant in understanding the molecular interactions precursive to cancer.
Ridler
P J
PJ
Jennings
B R
BR
Osborne
M
M
Brookes
P
P
D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D001551:Benz(a)Anthracenes / Q000378:metabolism; D001580:Benzopyrenes / Q000378:metabolism; D001665:Binding Sites; D002273:Carcinogens / Q000378:metabolism; D004247:DNA / Q000378:metabolism*; D018736:DNA Adducts; D004563:Electrochemistry; D004852:Epoxy Compounds / Q000378:metabolism; D005453:Fluorescence; D066298:In Vitro Techniques; D008748:Methylcholanthrene / Q000031:analogs & derivatives / Q000378:metabolism; D008956:Models, Chemical; D011083:Polycyclic Compounds / Q000378:metabolism*; D013237:Stereoisomerism
D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D002273:Carcinogens; D018736:DNA Adducts; D004852:Epoxy Compounds; D011083:Polycyclic Compounds; C043931:benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide-DNA; 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