4,6-Diamino-5-formamidopyrimidine, 8-hydroxyguanine and 8-hydroxyadenine in DNA from neoplastic liver of English sole exposed to carcinogens.
Attack of the hydroxyl radical on the 8-carbon of guanine results in the formation of 2,6-diamino-4-hydroxy-5-formamidopyrimidine (FapyGua). This modified nucleotide was recently found in neoplastic livers of wild English sole exposed to aromatic hydrocarbons (Malins et al., Carcinogenesis, 11, 1045-1047, 1990). Gas-chromatographic-mass spectrometric evidence reported here indicates that three other modified nucleotides are also present in the neoplastic liver: 4,6-diamino-5-formamidopyrimidine, 8-hydroxyguanine and 8-hydroxyadenine. These findings support the hypothesis that the purine nucleotides were modified by the hydroxyl radical and that these changes play a crucial role in tumor formation.
Malins
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DC
Environmental Biochemistry Program, Pacific Northwest Research Foundation, Seattle WA 98122.
Haimanot
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R
D000225:Adenine / Q000031:analogs & derivatives* / Q000378:metabolism; D000818:Animals; D002273:Carcinogens / Q000378:metabolism*; D004273:DNA, Neoplasm / Q000378:metabolism*; D005412:Flatfishes; D005609:Free Radicals; D006878:Hydroxides / Q000378:metabolism; D017665:Hydroxyl Radical; D008113:Liver Neoplasms / Q000378:metabolism* / Q000473:pathology; D011743:Pyrimidines / Q000378:metabolism*
D002273:Carcinogens; D004273:DNA, Neoplasm; D005609:Free Radicals; D006878:Hydroxides; D011743:Pyrimidines; C002992:8-hydroxyadenine; D017665:Hydroxyl Radical; C039544:4,6-diamino-5-N-formamidopyrimidine; D000225:Adenine