Some properties of vicinal diol-epoxides derived from benzo(a)anthracene and benzo(a)pyrene.
The alkylating properties of pairs of syn- and anti-isomers of 2 diol-epoxides derived from benzo(a)pyrene (BP) and of 1 derived from benz(a)anthracene (BA) have been investigated. Of the anti-diol-epoxides, anti-BP 7,8-diol-9,10-oxide was the most reactive compound towards DNA, towards sodium p-nitrothiophenolate in a non-aqueous solvent system, and towards 4-(p-nitrobenzyl)pyridine in aqueous solution; anti-BP 9,10,-diol-7,8-oxide was of intermediate reactivity and anti-BA 8,9-diol-10,11-oxide was least reactive. The syn-diol-epoxides gave unsatisfactory results with DNA and 4-(p-nitrobenzyl)pyridine because of their rapid solvolysis in aqueous solution, but with sodium p-nitrothiophenolate showed the order of reactivity syn-BP 7,8-diol-9,10-oxide greater than syn-BA 8,9-diol-10,11-oxide greater than syn-BP 9,10-diol-7,8-oxide. The products of the reaction between diol-epoxides and nucleic acids were examined by Sephadex LH-20 chromatography followed by high-pressure liquid chromatography (HPLC) and the diol-epoxides were shown to react principally with the guanosine and adenosine moieties of RNA.
D000477:Alkylating Agents; D001551:Benz(a)Anthracenes / Q000494:pharmacology*; D001580:Benzopyrenes / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA; D004852:Epoxy Compounds / Q000494:pharmacology; D009578:Nitrobenzenes; D011131:Polyribonucleotides; D011725:Pyridines; D012313:RNA; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds
D000477:Alkylating Agents; D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D004852:Epoxy Compounds; D009578:Nitrobenzenes; D011131:Polyribonucleotides; D011725:Pyridines; D013438:Sulfhydryl Compounds; D012313:RNA; D004247:DNA