Effect of Guanine Stacking on the Oxidation of 8-Oxoguanine in B-DNA

Prat, Ferran; Houk, K. N.; Foote, Christopher S.

doi:10.1021/ja972331q

Cited by 275 publications

(292 citation statements)

References 24 publications

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“…Whereas the above provide evidence of stability in extracellular matrices, it is worth noting that 8-oxodG is more prone to oxidation than dG due to its lower redox potential (80,81) and is preferentially oxidized even in the presence of an excess of Gua (82,83). By the same token, oxidation of Thy to thymine glycol is less likely to occur than Gua to 8-oxoGua due to the lower oxidation potential of Gua compared with Thy.…”

Section: Methods Of Analysismentioning

confidence: 96%

Measurement and Meaning of Oxidatively Modified DNA Lesions in Urine

Cooke

Oliński²,

Loft³

2008

Cancer Epidemiology, Biomarkers &Amp; Prevention

203

147

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Background: Oxidatively generated damage to DNA has been implicated in the pathogenesis of a wide variety of diseases. The noninvasive assessment of such damage, i.e., in urine, and application to large-scale human studies are vital to understanding this role and devising intervention strategies. Methods: We have reviewed the literature to establish the status quo with regard to the methods and meaning of measuring DNA oxidation products in urine. Results: Most of the literature focus upon 8-oxo-7,8-dihydro-2 ¶-deoxyguanosine (8-oxodG), and whereas a large number of these reports concern clinical conditions, there remains (a) lack of consensus between methods, (b) possible contribution from diet and/or cell death, (c) no definitive DNA repair source of urinary 2 ¶-deoxyribonucleoside lesions, and (d) no reference ranges for healthy or diseased individuals. Conclusions: The origin of 8-oxodG is not identified; however, recent cell culture studies suggest that the

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Section: Methods Of Analysismentioning

confidence: 96%

Measurement and Meaning of Oxidatively Modified DNA Lesions in Urine

Cooke

Oliński²,

Loft³

2008

Cancer Epidemiology, Biomarkers &Amp; Prevention

203

147

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“…The ionization potentials of base pairs in the stacked conformation have also been studied theoretically. [55][56][57] The vertical ionization potential of stacked bases and basepaired dinucleotides were calculated by Sugiyama and Saito 57 using 3-21G Ã and 6-31G Ã levels within Koopmans' approximation. With 6-31G Ã level of theory, the ionization potentials of G, GG, GGG, and GGGG were found to be 7.75, 7.28, 7.07, 6.98.…”

Section: Ionization Potential Of Dna Bases and Base Pairsmentioning

confidence: 99%

Theoretical Modeling of Radiation‐Induced DNA Damage

Kumar

Sevilla

2009

Radical and Radical Ion Reactivity in Nucleic Acid Chemistry

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“…Urate fits snugly into the active pocket, exposing the si-si face with effectively desolvated imidazolone subnucleus to the oxidative attack. The effect of heteroatom-71 stacking, reminiscent of enhanced reactivity toward oxidants caused by base stacking in B-form of DNA [9], may provide a new understanding of mechanisms underlying dioxygen activation by uricase. Selected stacking distances: N1-C8' = 3.424 (4) (4) 0.828(3) 0.036(7) 0.031 (5) 0.870(4) 0.053(9) 0.657 (5) 0.982(4) 0.057(9) 0.575 (5) 1.096(4) 0.06(1) …”

Section: Discussionmentioning

confidence: 99%