Direct formation of the C5'-radical in the sugar-phosphate backbone of DNA by high-energy radiation.

The Journal of Physical Chemistry. B
Amitava AdhikaryMichael D Sevilla

Abstract

Neutral sugar radicals formed in DNA sugar-phosphate backbone are well-established as precursors of biologically important damage such as DNA strand scission and cross-linking. In this work, we present electron spin resonance (ESR) evidence showing that the sugar radical at C5' (C5'(•)) is one of the most abundant (ca. 30%) sugar radicals formed by γ- and Ar ion-beam irradiated hydrated DNA samples. Taking dimethyl phosphate as a model of sugar-phosphate backbone, ESR and theoretical (DFT) studies of γ-irradiated dimethyl phosphate were carried out. CH(3)OP(O(2)(-))OCH(2)(•) is formed via deprotonation from the methyl group of directly ionized dimethyl phosphate at 77 K. The formation of CH(3)OP(O(2)(-))OCH(2)(•) is independent of dimethyl phosphate concentration (neat or in aqueous solution) or pH. ESR spectra of C5'(•) found in DNA and of CH(3)OP(O(2)(-))OCH(2)(•) do not show an observable β-phosphorus hyperfine coupling (HFC). Furthermore, C5'(•) found in DNA does not show a significant C4'-H β-proton HFC. Applying the DFT/B3LYP/6-31G(d) method, a study of conformational dependence of the phosphorus HFC in CH(3)OP(O(2)(-))OCH(2)(•) shows that in its minimum energy conformation, CH(3)OP(O(2)(-))OCH(2)(•), has a negligible β-p...Continue Reading

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May 28, 2009·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
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Jan 1, 2010·Physical Chemistry Chemical Physics : PCCP·Amitava AdhikaryMichael D Sevilla

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Citations

Feb 1, 2013·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
Aug 4, 2015·The Journal of Physical Chemistry. B·Amitava AdhikaryMichael D Sevilla
May 27, 2015·Radiation and Environmental Biophysics·Luděk VyšínMarie Davídková
Nov 3, 2016·Radiation and Environmental Biophysics·Paul J BlackJeffrey J Hayes
Apr 13, 2018·Chemistry : a European Journal·Takayuki WakakiMotomu Kanai
Mar 16, 2019·Chemistry : a European Journal·Katharine Moore Tibbetts
May 16, 2013·Physical Chemistry Chemical Physics : PCCP·Siv G AalbergsjøEinar Sagstuen
Oct 11, 2019·International Journal of Molecular Sciences·Jun MaMehran Mostafavi
Nov 14, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chryssostomos ChatgilialogluKrzysztof Bobrowski
Feb 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Derrick Ampadu BoatengKatharine Moore Tibbetts
Aug 23, 2018·The Journal of Physical Chemistry Letters·Jun MaMehran Mostafavi
Oct 9, 2014·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
Sep 17, 2021·Physical Chemistry Chemical Physics : PCCP·Aurélien de la LandeMehran Mostafavi

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