One-electron oxidation of DNA oligomers that lack guanine: reaction and strand cleavage at remote thymines by long-distance radical cation hopping

Journal of the American Chemical Society
Abraham JoyGary B Schuster

Abstract

The anthraquinone (AQ) photosensitized one-electron oxidation of DNA introduces a radical cation (electron "hole") that migrates through the duplex by hopping. The radical cation normally is trapped irreversibly by reaction at guanine. We constructed AQ-linked DNA oligomers composed exclusively of A/T base pairs. Their irradiation led to reaction and strand cleavage primarily at thymines. Long-distance radical cation hopping to distant thymines was demonstrated by the distance dependence of the process and by experiments with DNA oligomers that contain a single remote GG step. The reaction of the radical cation at thymine was shown to involve its 5-methyl group by the replacement of selected thymines with uracils. These findings show that the reactivity of radical cations in DNA cannot be explained simply by exclusive reliance on the relative oxidation potential of the nucleobases. Instead, the site of reaction is determined in accord with the Curtin-Hammett principle for reactive species in rapid equilibrium.

References

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Citations

Mar 11, 2010·Chemical Reviews·Joseph C Genereux, Jacqueline K Barton
Oct 16, 2008·Journal of the American Chemical Society·Joseph C GenereuxJacqueline K Barton
Jun 6, 2007·The Journal of Physical Chemistry. B·Amitava AdhikaryMichael D Sevilla
Sep 11, 2010·Chemical Communications : Chem Comm·Joshy Joseph, Gary B Schuster
Oct 15, 2013·The Journal of Chemical Physics·Amedeo CapobiancoAndrea Peluso
Dec 29, 2013·International Journal of Radiation Biology·Jean CadetNicholas E Geacintov
Jul 15, 2015·Physical Chemistry Chemical Physics : PCCP·Raffaele BorrelliAndrea Peluso
Jan 16, 2015·Physical Chemistry Chemical Physics : PCCP·Amedeo CapobiancoAndrea Peluso
Oct 19, 2006·Organic & Biomolecular Chemistry·Thabisile Ndlebe, Gary B Schuster
Feb 23, 2008·Organic & Biomolecular Chemistry·Avik GhoshJean Cadet
Mar 6, 2010·Organic & Biomolecular Chemistry·Sriram Kanvah, Gary B Schuster
Feb 14, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Joshy Joseph, Gary B Schuster
Oct 13, 2007·Physical Review Letters·Yves A MantzMichele Parrinello
Nov 11, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea PelusoAmedeo Capobianco
Sep 15, 2009·Journal of the American Chemical Society·Joshy Joseph, Gary B Schuster
Oct 18, 2007·Chemical Research in Toxicology·Hui Ding, Marc M Greenberg
Dec 9, 2017·The Journal of Physical Chemistry. B·Andy DangFrantišek Tureček
Jul 11, 2013·The Journal of Physical Chemistry. B·Amedeo CapobiancoAndrea Peluso

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