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Do TT, Tang VJ, Aguilera JA, et al. Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates. Radiat Phys Chem Oxf Engl 1993. 2010;79(1):1144-1148doi: 10.1016/j.radphyschem.2010.06.006.
Do, T. T., Tang, V. J., Aguilera, J. A., & Milligan, J. R. (2010). Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates. Radiation physics and chemistry (Oxford, England : 1993), 79(1), 1144-1148. https://doi.org/10.1016/j.radphyschem.2010.06.006
Do, Trinh T, et al. "Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates." Radiation physics and chemistry (Oxford, England : 1993) vol. 79,1 (2010): 1144-1148. doi: https://doi.org/10.1016/j.radphyschem.2010.06.006
Do TT, Tang VJ, Aguilera JA, Milligan JR. Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates. Radiat Phys Chem Oxf Engl 1993. 2010 Nov 01;79(1):1144-1148. doi: 10.1016/j.radphyschem.2010.06.006. PMID: 21966099; PMCID: PMC3182468.
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Radiat Phys Chem Oxf Engl 1993. 2010 Nov 01;79(1):1144-1148. doi: 10.1016/j.radphyschem.2010.06.006.

Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates.

Radiation physics and chemistry (Oxford, England : 1993)

Trinh T Do, Vicky J Tang, Joseph A Aguilera, Jamie R Milligan

Affiliations

  1. Department of Radiology, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0610.

PMID: 21966099 PMCID: PMC3182468 DOI: 10.1016/j.radphyschem.2010.06.006

Abstract

In DNA, guanine bases are the sites from which electrons are most easily removed. As a result of hole migration to this stable location on guanine, guanyl radicals are major intermediates in DNA damage produced by the direct effect of ionizing radiation (ionization of the DNA itself and not through the intermediacy of water radicals). We have modeled this process by employing gamma irradiation in the presence of thiocyanate ions, a method which also produces single electron oxidized guanyl radicals in plasmid DNA in aqueous solution. The stable products formed in DNA from these radicals are detected as strand breaks after incubation with the FPG protein. When a phenolic compound is present in solution during gamma irradiation, the formation of guanyl radical species is decreased by electron donation from the phenol to the guanyl radical. We have quantified the rate of this reaction for four different phenolic compounds bearing carboxylate substituents as proton acceptors. A comparison of the rates of these reactions with the redox strengths of the phenolic compounds reveals that salicylate reacts ca. 10-fold faster than its structural analogs. This observation is consistent with a reaction mechanism involving a proton coupled electron transfer, because intra-molecular transfer of a proton from the phenolic hydroxyl group to the carboxylate group is possible only in salicylate, and is favored by the strong 6-membered ring intra-molecular hydrogen bond in this compound.

References

  1. Radiat Res. 1993 Feb;133(2):151-7 - PubMed
  2. J Am Chem Soc. 2004 Feb 18;126(6):1682-7 - PubMed
  3. Chem Rev. 2003 Jul;103(7):2729-59 - PubMed
  4. Biochemistry. 2004 May 4;43(17):5102-8 - PubMed
  5. Int J Radiat Biol. 2006 Jun;82(6):421-33 - PubMed
  6. Int J Radiat Biol. 2000 Aug;76(8):1063-73 - PubMed
  7. Chem Rev. 1998 May 7;98(3):1089-1108 - PubMed
  8. J Am Chem Soc. 2009 Apr 15;131(14):5203-7 - PubMed
  9. J Am Chem Soc. 2006 Dec 20;128(50):15966-7 - PubMed
  10. Radiat Res. 1996 Mar;145(3):304-14 - PubMed
  11. J Am Chem Soc. 2006 May 3;128(17):5703-10 - PubMed
  12. J Biol Chem. 2001 Jul 6;276(27):24621-6 - PubMed
  13. Radiat Res. 2006 Jul;166(1 Pt 1):1-8 - PubMed
  14. Annu Rev Biochem. 2009;78:673-99 - PubMed
  15. Nat Chem Biol. 2006 Jul;2(7):348-9 - PubMed
  16. J Biol Chem. 1998 Nov 13;273(46):30116-21 - PubMed
  17. Chemistry. 2000 Feb 4;6(3):475-84 - PubMed
  18. Int J Radiat Biol. 2001 Nov;77(11):1095-108 - PubMed
  19. J Phys Chem B. 2005 Jul 14;109(27):13368-74 - PubMed
  20. J Am Chem Soc. 2006 Oct 11;128(40):13076-83 - PubMed
  21. J Am Chem Soc. 2008 Jul 23;130(29):9194-5 - PubMed
  22. Free Radic Res Commun. 1990;11(4-5):195-206 - PubMed
  23. Int J Radiat Biol. 2000 Oct;76(10):1305-14 - PubMed
  24. Acc Chem Res. 2008 Aug;41(8):1075-83 - PubMed
  25. Nature. 1974 Nov 22;252(5481):323-4 - PubMed
  26. Nucleic Acids Res. 1998 Nov 1;26(21):4935-42 - PubMed

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