Identification of novel 7,12-dimethylbenz[a]anthracene adducts in cellular ribonucleic acid.
The interaction of guanosine with 7,12-dimethylbenz[a]anthracene (DMBA) 5,6-oxide under alkaline conditions resulted in the formation of six derivatives. These six compounds were cochromatographed with nucleosides obtained by hydrolysis of RNA isolated from rat liver cells treated with [3H]DMBA. The cochromatography showed that three of these adducts were formed in cellular RNA. The three products constituted less than 5% of the total nucleoside-DMBA adducts as shown by chromatography on Sephadex LH-20 and high-pressure liquid chromatography. In one of them, the 2'-hydroxy group of the ribose moiety of guanosine was linked to the C-5, and in the second, to the C-6 position of the DMBA 5,6-oxide residue. In the third derivative, the C-8 position of guanosine was linked to the C-5 of the DMBA 5,6-oxide moiety. These results show, for the first time, modifications of the ribose moiety and of the guanine residue at the C-8 position in the cellular RNA by a metabolite of a polycyclic hydrocarbon.
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000031:analogs & derivatives / Q000378:metabolism*; D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism*; D002460:Cell Line; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000378:metabolism; D004852:Epoxy Compounds / Q000378:metabolism; D006151:Guanosine; D008099:Liver / Q000378:metabolism*; D012313:RNA / Q000378:metabolism*; D051381:Rats
D001551:Benz(a)Anthracenes; D004852:Epoxy Compounds; D006151:Guanosine; C012929:7,12-dimethylbenz(a)anthracene 5,6-oxide; D015127:9,10-Dimethyl-1,2-benzanthracene; D012313:RNA; D004247:DNA