A new synthetic route to nucleotide adducts derived from N-acetylated and unacetylated 4-aminobiphenyl
- 1 October 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Carcinogenesis: Integrative Cancer Research
- Vol. 9 (10) , 1817-1821
- https://doi.org/10.1093/carcin/9.10.1817
Abstract
The carcinogen N -acetoxy- N -2-acetylaminofluorene reacts with dG and dG-containing nucleotides to give good yields of the C-8 adducts, but the analogous 4-aminobiphenyl derivative does not. Replacement of the N -acetoxy group by 2, 6-dichlorobenzoyloxy circumvents this difficulty. This reaction is shown to be generally applicable, and biphenyl-amido adducts with dG, d(CpG), d(GpC) and d(ApG) have been prepared. A new, useful deacetylation procedure employing the heterogeneous system sodium carbonate/ methanol which leads to the corresponding biphenyamino derivative without appreciable imidazole ring opening is also reported.Keywords
This publication has 11 references indexed in Scilit:
- Conformation of d(CpG) modified by the carcinogen 4-aminobiphenyl: a combined experimental and theoretical analysisBiochemistry, 1986
- DNA binding and mutation spectra of the carcinogen N-2-aminofluorene in Escherichia coliJournal of Molecular Biology, 1985
- Formation and removal of DNA adducts in rat liver treated with N-hydroxy derivatives of 2-acetylaminofluorene, 4-acetylaminobiphenyl, and, 2-acetylaminophenanthreneCarcinogenesis: Integrative Cancer Research, 1984
- Acetylation of nucleosides by N-acetoxy-N-arylacetamides: dependence on base, aryl group, and buffer compositionThe Journal of Organic Chemistry, 1982
- New syntheses of N-(guanosin-8-yl)-4-aminobiphenyl and its 5′-monophosphateChemico-Biological Interactions, 1981
- Structural identification of the pyrimidine derivatives formed from N-(deoxyguanosin-8-yl)-2-aminofluorene in aqueous solution at alkaline pHCarcinogenesis: Integrative Cancer Research, 1980
- In vitro reaction of the carcinogen, N-hydroxy-2-naphthylamine, with DNA at the C-8 and N2 atoms of guanine and at the N6 atom of adenineCarcinogenesis: Integrative Cancer Research, 1980
- GUANYL O-6-ARYLAMINATION AND O-6-ARYLATION OF DNA BY CARCINOGEN N-HYDROXY-1-NAPHTHYLAMINE1978
- Comparative orientation of the fluorene residue in native DNA modified by N-acetoxy-N-2-acetylaminofluorene and two 7-halogeno derivativesBiochemistry, 1976
- Absorption and Optical Rotatory Dispersion of Seven Trinucleoside DiphosphatesJournal of Molecular Biology, 1965