Free Radical Formation in Purines: Crystals of Hypoxanthine Derivatives

Sibel Tokdemir Ozturk

Department of Physics and Astronomy, Georgia State University


The interaction of ionizing radiation with DNA and its hydration layer results in the production of free radical species trapped on either the bases or sugar phosphate backbone of the DNA. The objective of this work is to identify the radicals generated in hypoxanthine and its derivatives. Hypoxanthine is a purine and is closely related to DNA subunits that differ by the arrangement of hydrogens in the molecule. Single crystals of hypoxanthine derivatives were X-irradiated and investigated using K-band (24 GHz) electron paramagnetic resonance (EPR), electron-nuclear double resonance (ENDOR), and field-swept-ENDOR (FSE) techniques at 10 K. Immediately following irradiation at 10 K at least three different radicals were observed for hypoxanthine·HCl·H2O. For unique assignment of observed hyperfine couplings, partially deuterated crystals of hypoxanthine·HCl·H2O where used. Identified radicals are the N3?protonated anion radical and the N7-deprotonated cation radical. For inosine, the nucleoside of hypoxanthine base, at least five different radicals are formed immediately after irradiation at 10 K. Two of these were identified as the N1-deprotonated anion radical and C5’-H abstraction radical at the sugar ring. Evidence indicates that the third radical may be the O6-protonated anion. Analysis of the spectra following warming both hypoxanthine and sodium inosine crystals to room temperature showed that C8-H addition radical is the only observable radical.