Independent Generation of Reactive Intermediates Leads to an Alternative Mechanism for Strand Damage Induced by Hole Transfer in Poly(dA-T) Sequences

Journal of the American Chemical Society
Huabing SunMarc M Greenberg

Abstract

Purine radical cations (dA•+ and dG•+) are the primary hole carriers of DNA hole migration due to their favorable oxidation potential. Much less is known about the reactivity of higher energy pyrimidine radical cations. The thymidine radical cation (T•+) was produced at a defined position in DNA from a photochemical precursor for the first time. T•+ initiates hole transfer to dGGG triplets in DNA. Hole localization in a dGGG sequence accounts for ∼26% of T•+ formed under aerobic conditions in 9. Reduction to yield thymidine is also quantified. 5-Formyl-2'-deoxyuridine is formed in low yield in DNA when T•+ is independently generated. This is inconsistent with mechanistic proposals concerning product formation from electron transfer in poly(dA-T) sequences, following hole injection by a photoexcited anthraquinone. Additional evidence that is inconsistent with the original mechanism was obtained using hole injection by a photoexcited anthraquinone in DNA. Instead of requiring the intermediacy of T•+, the strand damage patterns observed in those studies, in which thymidine is oxidized, are reproduced by independent generation of 2'-deoxyadenosin- N6-yl radical (dA•). Tandem lesion formation by dA• provides the basis for an alterna...Continue Reading

References

Aug 22, 1996·Nature·D B HallJ K Barton
Jun 28, 2001·Journal of the American Chemical Society·M NewcombD Crich
Jul 18, 2001·Journal of the American Chemical Society·J H Horner, M Newcomb
Jul 26, 2002·Journal of the American Chemical Society·Akinari YokoyaPeter O'Neill
Aug 6, 2002·Free Radical Biology & Medicine·Jean CadetJean-Luc Ravanat
Oct 30, 2003·Journal of the American Chemical Society·K Nolan Carter, Marc M Greenberg
May 12, 2004·Biochemistry·Daniel K RogstadLawrence C Sowers
Nov 13, 2004·Journal of the American Chemical Society·John H HornerMartin Newcomb
Jul 21, 2006·The Journal of Physical Chemistry. B·Shubhadeep PurkayasthaWilliam A Bernhard
Nov 21, 2007·Angewandte Chemie·Goutam Chowdhury, F Peter Guengerich
Feb 23, 2008·Organic & Biomolecular Chemistry·Avik GhoshJean Cadet
Jun 6, 2009·Chemical Research in Toxicology·Goutam Chowdhury, F Peter Guengerich
Nov 27, 2009·Accounts of Chemical Research·Sriram KanvahUzi Landman
Mar 6, 2010·Organic & Biomolecular Chemistry·Sriram Kanvah, Gary B Schuster
Mar 11, 2010·Chemical Reviews·Joseph C Genereux, Jacqueline K Barton
Sep 11, 2010·Chemical Communications : Chem Comm·Joshy Joseph, Gary B Schuster
Feb 26, 2011·Journal of the American Chemical Society·Joseph C GenereuxJacqueline K Barton
Feb 15, 2012·Journal of the American Chemical Society·Yekaterina RokhlenkoVladimir Shafirovich
Feb 1, 2013·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
Feb 21, 2013·Journal of the American Chemical Society·Robert N BarnettGary B Schuster
Apr 3, 2014·Journal of the American Chemical Society·Yekaterina RokhlenkoVladimir Shafirovich
Dec 11, 2012·Journal of Chemical Theory and Computation·Brian T PsciukH Bernhard Schlegel
Apr 16, 2016·Journal of the American Chemical Society·Michelle A HarrisFrederick D Lewis
Apr 30, 2017·Chemical Science·Mamoru Fujitsuka, Tetsuro Majima
Jul 25, 2017·Journal of the American Chemical Society·Akos BanyaszDimitra Markovitsi
Oct 11, 2017·The Journal of Organic Chemistry·Huabing SunMarc M Greenberg
May 9, 2018·Journal of the American Chemical Society·Liwei Zheng, Marc M Greenberg

❮ Previous
Next ❯

Citations

Oct 11, 2019·International Journal of Molecular Sciences·Jun MaMehran Mostafavi
May 5, 2020·Angewandte Chemie·Liwei ZhengMarc M Greenberg
Jun 28, 2019·Journal of the American Chemical Society·Huabing SunMarc M Greenberg
Sep 2, 2021·Journal of the American Chemical Society·Haihui PengMarc M Greenberg
Sep 28, 2021·Chembiochem : a European Journal of Chemical Biology·Hans-Achim Wagenknecht

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cell Migration

Cell migration is involved in a variety of physiological and pathological processes such as embryonic development, cancer metastasis, blood vessel formation and remoulding, tissue regeneration, immune surveillance and inflammation. Here is the latest research.