title: Xanthine oxidase-catalyzed DNA binding of dihydrodiol derivatives of nitro-polycyclic aromatic hydrocarbons.
abstract: Xanthine oxidase, a mammalian nitroreductase, catalyzed the covalent binding of a series of nitro-polycyclic aromatic hydrocarbons (nitro-PAHs) trans-dihydrodiols to DNA. Some of the trans-dihydrodiols bound to DNA to a greater extent than their parent nitro-PAHs; however, when the dihydrodiol moiety was peri to the nitro substituent low levels of binding were observed. These data illustrate that ring-oxidation and hydrolysis of nitro-PAHs to their trans-dihydrodiols followed by nitroreduction is a potential metabolic pathway leading to DNA adducts in mammals.
mesh_terms: D000818:Animals; D000873:Anthracenes / Q000378:metabolism; D001551:Benz(a)Anthracenes / Q000378:metabolism; D001580:Benzopyrenes / Q000378:metabolism; D001711:Biotransformation; D004247:DNA / Q000378:metabolism*; D004249:DNA Damage; D066298:In Vitro Techniques; D008862:Microsomes, Liver / Q000378:metabolism*; D009574:Nitro Compounds / Q000378:metabolism*; D011083:Polycyclic Compounds / Q000378:metabolism*; D051381:Rats; D013329:Structure-Activity Relationship; D014969:Xanthine Oxidase / Q000378:metabolism*
chemical_list: D000873:Anthracenes; D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D009574:Nitro Compounds; D011083:Polycyclic Compounds; C038954:7-nitrobenzanthracene; C040217:1-nitrobenzo(a)pyrene; D004247:DNA; D014969:Xanthine Oxidase; C035016:9-nitroanthracene