Issue 5, 1995

EPR Spin-trapping studies of the reaction of radicals derived from hydroperoxide tumour-promoters with nucleic acids and their components

Abstract

EPR spin trapping experiments using the spin trap Me3CNO have been used to identify radicals formed on reaction of ButO˙ and PhC(CH3)2O˙[generated from reaction of the tumour promoter compounds ButO2H and PhC(CH3)2O2H with TiIII] with a variety of pyrimidine and purine derivatives, as well as RNA and DNA. The observed radical adducts can be rationalized in terms of addition of the alkoxyl radical to the C5–C6 double bond of the pyrimidine base and ring positions on the purine derivatives, as well as hydrogen abstraction at the sugar moiety; the latter process is believed to be a minor pathway and may occur as a result of radical transfer from the base to sugar moieties. Comparison of the experimental data with that obtained previously with HO˙ shows that the ButO˙ and PhC(CH3)2O˙ radicals exhibit different regioselectivities than the former species. Experiments carried out with DNA, RNA and polynucleosides provide direct evidence for alkoxyl radical attack on these macromolecules; such reactions may play a role in the tumour-promoting activity of these hydroperoxides.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1995, 895-901

EPR Spin-trapping studies of the reaction of radicals derived from hydroperoxide tumour-promoters with nucleic acids and their components

C. Hazlewood and M. J. Davies, J. Chem. Soc., Perkin Trans. 2, 1995, 895 DOI: 10.1039/P29950000895

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