ArticleThe journal of physical chemistry. B2015
π-Radical to σ-Radical Tautomerization in One-Electron-Oxidized 1-Methylcytosine and Its Analogs.
Article in The journal of physical chemistry. B, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 23 citations in OpenAlex.
- The Site of Azido Substitution in a Pyrimidine Nucleobase Dictates the Type of Nitrogen-Centered Radical Formed after Dissociative Electron Attachment.The journal of physical chemistry. B · 2025Article
- Azido derivatives of sesquiterpene lactones: Synthesis, anticancer proliferation, and chemistry of nitrogen-centered radicals.Results in chemistry · 2024Article
- Nitrogen-Centered Radicals Derived from Azidonucleosides.Molecules (Basel, Switzerland) · 2024Review
- Photochemical and Single Electron Transfer Generation of 2'-Deoxycytidin-The Journal of organic chemistry · 2023Article
- Proton-Transfer Reactions in One-Electron-Oxidized G-Quadruplexes: A Density Functional Theory Study.The journal of physical chemistry. B · 2022Article
- Reactivity and DNA Damage by Independently Generated 2'-Deoxycytidin-Journal of the American Chemical Society · 2021Article
- Site of Azido Substitution in the Sugar Moiety of Azidopyrimidine Nucleosides Influences the Reactivity of Aminyl Radicals Formed by Dissociative Electron Attachment.The journal of physical chemistry. B · 2020Article
- Reaction of Electrons with DNA: Radiation Damage to Radiosensitization.International journal of molecular sciences · 2019Review
- Excited States of One-Electron Oxidized Guanine-Cytosine Base Pair Radicals: A Time Dependent Density Functional Theory Study.The journal of physical chemistry. A · 2019Article
- Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells.Organic letters · 2018Article
- SOMO-HOMO Level Inversion in Biologically Important Radicals.The journal of physical chemistry. B · 2018Article
- Modulating the Catalytic Activity of Cerium Oxide Nanoparticles with the Anion of the Precursor Salt.The journal of physical chemistry. C, Nanomaterials and interfaces · 2017Article
- Cytosine Iminyl Radical (cytNThe journal of physical chemistry. A · 2017Article
- Prehydrated One-Electron Attachment to Azido-Modified Pentofuranoses: Aminyl Radical Formation, Rapid H-Atom Transfer, and Subsequent Ring Opening.The journal of physical chemistry. B · 2017Article
- Gamma and Ion-Beam Irradiation of DNA: Free Radical Mechanisms, Electron Effects, and Radiation Chemical Track Structure.Radiation physics and chemistry (Oxford, England : 1993) · 2016Article
- Effects of ionization on stability of 1-methylcytosine - DFT and PCM studies.Journal of molecular modeling · 2016Article
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7 authors at 1 institution in 1 country.
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Abstract
In this work, iminyl σ-radical formation in several one-electron-oxidized cytosine analogs, including 1-MeC, cidofovir, 2'-deoxycytidine (dCyd), and 2'-deoxycytidine 5'-monophosphate (5'-dCMP), were investigated in homogeneous, aqueous (D2O or H2O) glassy solutions at low temperatures by employing electron spin resonance (ESR) spectroscopy. Upon employing density functional theory (DFT) (DFT/B3LYP/6-31G* method), the calculated hyperfine coupling constant (HFCC) values of iminyl σ-radical agree quite well with the experimentally observed ones, thus confirming its assignment. ESR and DFT studies show that the cytosine iminyl σ-radical is a tautomer of the deprotonated cytosine π-cation radical [cytosine π-aminyl radical, C(N4-H)(•)]. Employing 1-MeC samples at various pHs ranging from ca. 8 to 11, ESR studies show that the tautomeric equilibrium between C(N4-H)(•) and the iminyl σ-radical at low temperature is too slow to be established without added base. ESR and DFT studies agree that, in the iminyl σ-radical, the unpaired spin is localized on the exocyclic nitrogen (N4) in an in-plane pure p-orbital. This gives rise to an anisotropic nitrogen hyperfine coupling (Azz = 40 G) from N4 and a near isotropic β-nitrogen coupling of 9.7 G from the cytosine ring nitrogen at N3. Iminyl σ-radical should exist in its N3-protonated form, as the N3-protonated iminyl σ-radical is stabilized in solution by over 30 kcal/mol (ΔG = -32 kcal/mol) over its conjugate base, the N3-deprotonated form. This is the first observation of an isotropic β-hyperfine ring nitrogen coupling in an N-centered DNA radical. Our theoretical calculations predict that the cytosine iminyl σ-radical can be formed in double-stranded DNA by a radiation-induced ionization-deprotonation process that is only 10 kcal/mol above the lowest energy path.
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