Journal of the Chemical Society. Perkin transactions I p. 3196 - 3204 (1981)
Update date:2022-08-11
Topics:
Blackburn, G. Michael
Flavell, Andrew J.
Orgee, Lawrence
Will, James P.
Williams, Gillian M.
Syntheses are described for the preparation of <9(10)-(3)H>anthracene, <6-(3)H>benzopyrene, and <7-Me-(3)H1>-7,12-dimethylbenzanthracene.The nature and extent of covalent binding of these hydrocarbons to calf thymus DNA resulting from ultraviolet or gamma irradiation, from oxidative processes involving iodine or hydrogen peroxide, or from oxygen in conjunction with NADPH and a rat liver microsomal preparation is investigated.The displacement of tritium on hydrocarbon bonding to DNA identifies position-6 in benzopyrene and position-9 in anthracene as sites for DNA binding by irradiation processes or by chemical oxidation.Metabolic binding of benzopyrene to DNA shows an altered regioselectivity while that for 7,12-dimethylbenzanthracene appears to involve the 7-methyl group.
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