PMID: 8601758Jan 1, 1996Paper

Reactions of sulphonyl peroxyl radicals with DNA and its components: hydrogen abstraction from the sugar backbone versus addition to pyrimidine double bonds

International Journal of Radiation Biology
Y Razskazovskii, Michael D Sevilla

Abstract

The reactions of sulphonyl peroxyl radicals with DNA and its components at low temperatures are investigated through use of electron spin resonance spectroscopy. Radiolysis of cysteine sulphinic acid solution in oxygenated aqueous 5 mol dm-3 LiCl glass has been employed to generate sulphonyl peroxyl radicals, CysSO2OO.. The mechanism of production is a two-step process involving the oxidation of the sulphinate (CysSO2-) to the sulphonyl radical (CysSO2.) by radiolytically produced Cl2- followed by oxygen addition to CysSO2.. Sulphonyl peroxyls are shown to be reactive toward DNA and nucleotides in low temperature glasses, giving rise to carbon-based peroxyl radicals. However, of the DNA bases only thymine was found to react readily. The thymine methyl group contains a relatively weak C-H bond which makes it easily abstractable. DNA nucleosides and nucleotides are likely attacked by CysSO2OO. by abstraction from the sugar C-H bonds. The C(1) position of deoxyribose ring of model nucleosides is suggested to be a preferred site for attack at low temperatures. The reaction with double-stranded DNA at higher temperatures may occur at the more accessible C(4) position. CysSO2OO. is also shown to react with a number of methyl substitu...Continue Reading

References

Aug 30, 1988·Biochemical and Biophysical Research Communications·M D SevillaD Becker
Jan 1, 1988·Pharmacology & Therapeutics·R C Fahey
Jan 1, 1987·International Journal of Radiation Biology and Related Studies in Physics, Chemistry, and Medicine·M S AkhlaqC von Sonntag
Oct 1, 1986·International Journal of Radiation Biology and Related Studies in Physics, Chemistry, and Medicine·M Quintiliani
Jan 1, 1983·Radiation and Environmental Biophysics·G SimoneM Quintiliani
May 1, 1994·International Journal of Radiation Biology·D BeckerM D Sevilla

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Citations

Sep 17, 1999·Free Radical Research·A V KachurJ E Biaglow
Dec 22, 1999·Biochemistry·H RodriguezJ Termini
Feb 20, 2003·Journal of the American Chemical Society·Luis E Ramírez-ArizmendiHilkka I Kenttämaa

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