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Solvent exposure associated with single abasic sites alters the base sequence dependence of oxidation of guanine in DNA in GG sequence contexts.
Chembiochem 2011; 12(11):1731-9C

Abstract

The effect of exposure of guanine in double-stranded oligonucleotides to aqueous solvent during oxidation by one-electron oxidants was investigated by introducing single synthetic tetrahydrofuran-type abasic sites (Ab) either adjacent to or opposite tandem GG sequences. The selective oxidation of guanine was initiated by photoexcitation of the aromatic sensitizers riboflavin and a pyrene derivative, and by the relatively small negatively charged carbonate radical anion. The relative rates of oxidation of the 5'- and 3' side G in runs of 5'⋅⋅⋅GG⋅⋅⋅ (evaluated by standard hot alkali treatment of the damaged DNA strand followed by high resolution gel electrophoresis of the cleavage fragments) are markedly affected by adjacent abasic sites either on the same or opposite strand. For example, in fully double-stranded DNA or one with an Ab adjacent to the 5'-G, the 5'-G/3'-G damage ratio is ≥4, but is inverted (<1.0) with the Ab adjacent to the 3'-G. These striking effects of Ab are attributed to the preferential localization of the "hole" on the most solvent-exposed guanine regardless of the size, charge, or reduction potential of the oxidizing species.

Authors+Show Affiliations

Department of Chemistry, Kyungpook National University, Daegu 702-701, Korea.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

21656632

Citation

Lee, Young-Ae, et al. "Solvent Exposure Associated With Single Abasic Sites Alters the Base Sequence Dependence of Oxidation of Guanine in DNA in GG Sequence Contexts." Chembiochem : a European Journal of Chemical Biology, vol. 12, no. 11, 2011, pp. 1731-9.
Lee YA, Liu Z, Dedon PC, et al. Solvent exposure associated with single abasic sites alters the base sequence dependence of oxidation of guanine in DNA in GG sequence contexts. Chembiochem. 2011;12(11):1731-9.
Lee, Y. A., Liu, Z., Dedon, P. C., Geacintov, N. E., & Shafirovich, V. (2011). Solvent exposure associated with single abasic sites alters the base sequence dependence of oxidation of guanine in DNA in GG sequence contexts. Chembiochem : a European Journal of Chemical Biology, 12(11), pp. 1731-9. doi:10.1002/cbic.201100140.
Lee YA, et al. Solvent Exposure Associated With Single Abasic Sites Alters the Base Sequence Dependence of Oxidation of Guanine in DNA in GG Sequence Contexts. Chembiochem. 2011 Jul 25;12(11):1731-9. PubMed PMID: 21656632.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Solvent exposure associated with single abasic sites alters the base sequence dependence of oxidation of guanine in DNA in GG sequence contexts. AU - Lee,Young-Ae, AU - Liu,Zhi, AU - Dedon,Peter C, AU - Geacintov,Nicholas E, AU - Shafirovich,Vladimir, Y1 - 2011/06/07/ PY - 2011/02/28/received PY - 2011/6/10/entrez PY - 2011/6/10/pubmed PY - 2012/1/10/medline SP - 1731 EP - 9 JF - Chembiochem : a European journal of chemical biology JO - Chembiochem VL - 12 IS - 11 N2 - The effect of exposure of guanine in double-stranded oligonucleotides to aqueous solvent during oxidation by one-electron oxidants was investigated by introducing single synthetic tetrahydrofuran-type abasic sites (Ab) either adjacent to or opposite tandem GG sequences. The selective oxidation of guanine was initiated by photoexcitation of the aromatic sensitizers riboflavin and a pyrene derivative, and by the relatively small negatively charged carbonate radical anion. The relative rates of oxidation of the 5'- and 3' side G in runs of 5'⋅⋅⋅GG⋅⋅⋅ (evaluated by standard hot alkali treatment of the damaged DNA strand followed by high resolution gel electrophoresis of the cleavage fragments) are markedly affected by adjacent abasic sites either on the same or opposite strand. For example, in fully double-stranded DNA or one with an Ab adjacent to the 5'-G, the 5'-G/3'-G damage ratio is ≥4, but is inverted (<1.0) with the Ab adjacent to the 3'-G. These striking effects of Ab are attributed to the preferential localization of the "hole" on the most solvent-exposed guanine regardless of the size, charge, or reduction potential of the oxidizing species. SN - 1439-7633 UR - https://www.unboundmedicine.com/medline/citation/21656632/Solvent_exposure_associated_with_single_abasic_sites_alters_the_base_sequence_dependence_of_oxidation_of_guanine_in_DNA_in_GG_sequence_contexts_ L2 - https://doi.org/10.1002/cbic.201100140 DB - PRIME DP - Unbound Medicine ER -