The biological activity of single-stranded ΦX174 DNA, modified by N-hydroxy-2-aminofluorene, is inhibited by guanine imidazole ring-opening of the major, non-lethal aminofluorene-DNA adduct
| Autor: | J. Retèl, J.G. Westra, E. Kriek, Maarten C. Welling, J.T. Lutgerink, Henk Loman |
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| Rok vydání: | 1986 |
| Předmět: |
Fluorenes
Cancer Research Guanine Stereochemistry Bacteriophage phi X174 Deoxyguanosine General Medicine medicine.disease_cause Adduct chemistry.chemical_compound chemistry Biochemistry DNA Viral DNA adduct medicine Trifluoroacetic acid Nucleic Acid Conformation Imidazole Escherichia coli Bacteriophage phi X 174 DNA |
| Zdroj: | Carcinogenesis. 7:1359-1364 |
| ISSN: | 1460-2180 0143-3334 |
| DOI: | 10.1093/carcin/7.8.1359 |
| Popis: | The major aminofluorene-DNA derivative, found in the liver of rats after administration of the hepatocarcinogen N-acetyl-2-aminofluorene and identified as N-(deoxyguanosin-8-yl)-2-aminofluorene (dGuo-C8-AF), was introduced in different amounts in single-stranded phi X174 DNA by reacting the DNA with tritium labeled N-hydroxy-2-aminofluorene. The modified DNA was subsequently incubated in 0.1 M NaOH at 37 degrees C for increasing periods of time to convert the dGuo-C8-AF residues into their guanine imidazole ring-opened forms. The degree of conversion was determined by measuring the amount of residual N-(guanin-8-yl)-2-aminofluorene in trifluoroacetic acid hydrolyzates of the alkali-treated DNA by h.p.l.c. In addition, the effect of ring opening on the biological activity of the DNA was monitored by transfecting the DNA to Escherichia coli wild-type spheroplasts. The results indicate that the major aminofluorene-DNA adduct formed initially, which contributes little to inactivation, becomes lethal when its guanine imidazole ring is opened. |
| Databáze: | OpenAIRE |
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