ArticleJournal of the American Chemical Society2012
Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
46 citing papers in PubMed, 105 citations in OpenAlex.
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- Hemin Recapitulates the Labile Iron Pool in the Cellular Fenton Reaction with DNA.Chemical research in toxicology · 2026Article
- Single-Molecule Chemistry Part II: Pathway Analysis of the Oxidation of Guanine to 8-Oxo-7,8-dihydroguanosine in an Oligonucleotide Hybrid.Molecules (Basel, Switzerland) · 2026Article
- Telomeric DNA damage landscapes distinguish oxidative from inflammatory cellular stress.Nucleic acids research · 2025Article
- Why the ROS matters: One-electron oxidants focus DNA damage and repair on G-quadruplexes for gene regulation.DNA repair · 2025Review
- DNA-Histone Cross-Link Formation via Hole Trapping in Nucleosome Core Particles.Journal of the American Chemical Society · 2023Article
- Hydroxyl Radical vs. One-Electron Oxidation Reactivities in an Alternating GC Double-Stranded Oligonucleotide: A New Type Electron Hole Stabilization.Biomolecules · 2023Article
- Chemistry of ROS-mediated oxidation to the guanine base in DNA and its biological consequences.International journal of radiation biology · 2022Article
- Reactivity and DNA Damage by Independently Generated 2'-Deoxycytidin-Journal of the American Chemical Society · 2021Article
- The Two Faces of the Guanyl Radical: Molecular Context and Behavior.Molecules (Basel, Switzerland) · 2021Review
- Excision of Oxidatively Generated Guanine Lesions by Competitive DNA Repair Pathways.International journal of molecular sciences · 2021Review
- Dependence of Fluorescence Quenching of CY3 Oligonucleotide Conjugates on the Oxidation Potential of the Stacking Base Pair.Molecules (Basel, Switzerland) · 2020Article
- On the irrelevancy of hydroxyl radical to DNA damage from oxidative stress and implications for epigenetics.Chemical Society reviews · 2020Review
- Iron Fenton oxidation of 2'-deoxyguanosine in physiological bicarbonate buffer yields products consistent with the reactive oxygen species carbonate radical anion not the hydroxyl radical.Chemical communications (Cambridge, England) · 2020Article
- Independent Generation and Time-Resolved Detection of 2'-Deoxyguanosin-N2-yl Radicals.Angewandte Chemie (International ed. in English) · 2020Article
- Independent Generation and Reactivity of 2'-Deoxyguanosin-The Journal of organic chemistry · 2020Article
- Inhibition of Excision of Oxidatively Generated Hydantoin DNA Lesions by NEIL1 by the Competitive Binding of the Nucleotide Excision Repair Factor XPC-RAD23B.Biochemistry · 2020Article
- On the epigenetic role of guanosine oxidation.Redox biology · 2020Review
- Sulfur-centered hemi-bond radicals as active intermediates in S-DNA phosphorothioate oxidation.Nucleic acids research · 2019Article
- HumanJournal of the American Chemical Society · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
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-guanine (5'-G*CT* and 5'-T*CG*). Alternatively, G(-H)(•) can be oxidized further by reaction with CO(3)(•-), generating the two-electron oxidation products 8-oxoG (C8 addition) and 5-carboxamido-5-formamido-2-iminohydantoin (2Ih, by C5 addition). The four-electron oxidation products, guanidinohydantoin (Gh) and spiroiminodihydantoin (Sp), appear only after a second (or more) laser pulse. The levels of all products, except 8-oxoG, which remains at a low constant value, increase with the number of laser pulses.
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