ArticleThe Journal of organic chemistry2015
5-Carboxamido-5-formamido-2-iminohydantoin, in Addition to 8-oxo-7,8-Dihydroguanine, Is the Major Product of the Iron-Fenton or X-ray Radiation-Induced Oxidation of Guanine under Aerobic Reducing Conditions in Nucleoside and DNA Contexts.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed.
- Hemin Recapitulates the Labile Iron Pool in the Cellular Fenton Reaction with DNA.Chemical research in toxicology · 2026Article
- OGG1 and MUTYH DNA Glycosylases, the Dynamic Duo Against 8-Oxoguanine DNA Lesion: Structure, Regulation, and Novel Emerging Roles.Biomolecules · 2026Review
- Hole Transfer and the Resulting DNA Damage.Biomolecules · 2024Review
- The Influence of 2'-Deoxyguanosine Lesions on the Electronic Properties ofMolecules (Basel, Switzerland) · 2024Review
- The Influence of Oxidized Imino-Allantoin in the Presence ofInternational journal of molecular sciences · 2024Article
- The 2Ih andMolecules (Basel, Switzerland) · 2023Article
- Chemistry of ROS-mediated oxidation to the guanine base in DNA and its biological consequences.International journal of radiation biology · 2022Article
- 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
- Products of Oxidative Guanine Damage Form Base Pairs with Guanine.International journal of molecular sciences · 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 Reactivity of 2'-Deoxyguanosin-The Journal of organic chemistry · 2020Article
- Synthesis of Oligonucleotides Containing the NChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Interplay of Guanine Oxidation and G-Quadruplex Folding in Gene Promoters.Journal of the American Chemical Society · 2020Article
- Article
- HumanJournal of the American Chemical Society · 2019Article
- 8-Oxo-7,8-dihydro-2'-deoxyguanosine and abasic site tandem lesions are oxidation prone yielding hydantoin products that strongly destabilize duplex DNA.Organic & biomolecular chemistry · 2017Article
- 8-Oxo-7,8-dihydroguanine, friend and foe: Epigenetic-like regulator versus initiator of mutagenesis.DNA repair · 2017Review
- Formation and processing of DNA damage substrates for the hNEIL enzymes.Free radical biology & medicine · 2017Review
- Formation and repair of oxidatively generated damage in cellular DNA.Free radical biology & medicine · 2017Review
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3 authors.
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Abstract
Exogenously and endogenously produced reactive oxygen species attack the base and sugar moieties of DNA showing a preference for reaction at 2'-deoxyguanosine (dG) sites. In the present work, dG was oxidized by HO(•) via the Fe(II)-Fenton reaction or by X-ray radiolysis of water. The oxidized lesions observed include the 2'-deoxynucleosides of 8-oxo-7,8-dihydroguanine (dOG), spiroiminodihydantoin (dSp), 5-guanidinohydantoin (dGh), oxazolone (dZ), 5-carboxamido-5-formamido-2-iminohydantoin (d2Ih), 5',8-cyclo-2'-deoxyguanosine (cyclo-dG), and the free base guanine (Gua). Reactions conducted with ascorbate or N-acetylcysteine as a reductant under aerobic conditions identified d2Ih as the major lesion formed. Studies were conducted to identify the role of O2 and the reductant in product formation. From these studies, mechanisms are proposed to support d2Ih as a major oxidation product detected under aerobic conditions in the presence of the reductant. These nucleoside observations were then validated in oxidations of oligodeoxynucleotide and λ-DNA contexts that demonstrated high yields of d2Ih in tandem with dOG, dSp, and dGh. These results identify dG oxidation to d2Ih to occur in high yields leading to a hypothesis that d2Ih could be found from in cells stressed with HO(•). Further, the distorted ring structure of d2Ih likely causes this lesion to be highly mutagenic.
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