Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions.

Journal of the American Chemical Society
Yekaterina RokhlenkoVladimir Shafirovich

Abstract

The exposure of guanine in the oligonucleotide 5'-d(TCGCT) to one-electron oxidants leads initially to the formation of the guanine radical cation G(•+), its deptotonation product G(-H)(•), and, ultimately, various two- and four-electron oxidation products via pathways that depend on the oxidants and reaction conditions. We utilized single or successive multiple laser pulses (308 nm, 1 Hz rate) to generate the oxidants CO(3)(•-) and SO(4)(•-) (via the photolysis of S(2)O(8)(2-) in aqueous solutions in the presence and absence of bicarbonate, respectively) at concentrations/pulse that were ∼20-fold lower than the concentration of 5'-d(TCGCT). Time-resolved absorption spectroscopy measurements following single-pulse excitation show that the G(•+) radical (pK(a) = 3.9) can be observed only at low pH and is hydrated within 3 ms at pH 2.5, thus forming the two-electron oxidation product 8-oxo-7,8-dihydroguanosine (8-oxoG). At neutral pH, and single pulse excitation, the principal reactive intermediate is G(-H)(•), which, at best, reacts only slowly with H(2)O and lives for ∼70 ms in the absence of oxidants/other radicals to form base sequence-dependent intrastrand cross-links via the nucleophilic addition of N3-thymidine to C8-guani...Continue Reading

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Citations

Sep 22, 2012·Chemical Research in Toxicology·Manicka V VadhanamRamesh C Gupta
Jun 6, 2013·Chemical Research in Toxicology·Guru S MadugunduVladimir Shafirovich
Jul 25, 2012·Physical Chemistry Chemical Physics : PCCP·Mariana P SerranoAndrés H Thomas
Oct 3, 2013·PLoS Genetics·Albino BacollaKaren M Vasquez
Dec 29, 2013·International Journal of Radiation Biology·Jean CadetNicholas E Geacintov
Apr 9, 2015·Chemical Research in Toxicology·Aaron M FlemingCynthia J Burrows
Apr 23, 2015·Chemical Communications : Chem Comm·A LatusE Maisonhaute
Jun 21, 2017·Science Advances·Jialong JieHongmei Su
Aug 16, 2016·Physical Chemistry Chemical Physics : PCCP·Shuang ZhaoZe-Sheng Li
Apr 22, 2018·Photochemistry and Photobiology·Tomasz J MertaVladimir Shafirovich
May 5, 2020·Angewandte Chemie·Liwei ZhengMarc M Greenberg
Aug 26, 2014·Journal of Physical Organic Chemistry·Anna H WolnaCynthia J Burrows
Jul 16, 2013·Chemical Communications : Chem Comm·Linda FeketeováRichard A J O'Hair
Jun 30, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Evangelos BalanikasDimitra Markovitsi
May 29, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mariana P SerranoAndrés H Thomas
Aug 14, 2020·Chemical Society Reviews·Aaron M Fleming, Cynthia J Burrows
Jan 27, 2021·Free Radical Research·Chryssostomos ChatgilialogluMichael A Terzidis
Jan 14, 2020·Redox Biology·Marco GiorgioPier Giuseppe Pelicci
Nov 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jens Sobek, Ralph Schlapbach
Nov 8, 2016·Free Radical Biology & Medicine·Vladimir Shafirovich, Nicholas E Geacintov
Apr 4, 2021·International Journal of Molecular Sciences·Vladimir Shafirovich, Nicholas E Geacintov
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chryssostomos Chatgilialoglu
Aug 3, 2021·Free Radical Biology & Medicine·Sandra EstébanezCarolina Lorente
Dec 17, 2014·Journal of the American Chemical Society·Lidan WuHongmei Su
Oct 2, 2019·Chemical Research in Toxicology·Sebastien P Hebert, H Bernhard Schlegel
May 7, 2014·Chemical Research in Toxicology·Stéphanie SilermeJean-Luc Ravanat
Apr 3, 2014·Journal of the American Chemical Society·Yekaterina RokhlenkoVladimir Shafirovich

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