ArticleThe journal of physical chemistry. B2010
Formation of aminyl radicals on electron attachment to AZT: abstraction from the sugar phosphate backbone versus one-electron oxidation of guanine.
Article in The journal of physical chemistry. B, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 22 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
- Pathways of the Dissociative Electron Attachment Observed in 5- and 6-Azidomethyluracil Nucleosides: Nitrogen (NThe journal of physical chemistry. B · 2023Article
- 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
- Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells.Organic letters · 2018Article
- 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
- π-Radical to σ-Radical Tautomerization in One-Electron-Oxidized 1-Methylcytosine and Its Analogs.The journal of physical chemistry. B · 2015Article
- 5-Thiocyanato-2'-deoxyuridine as a possible radiosensitizer: electron-induced formation of uracil-C5-thiyl radical and its dimerization.Physical chemistry chemical physics : PCCP · 2015Article
- One-electron oxidation of gemcitabine and analogs: mechanism of formation of C3' and C2' sugar radicals.Journal of the American Chemical Society · 2014Article
- Visible-light sensitization of vinyl azides by transition-metal photocatalysis.Angewandte Chemie (International ed. in English) · 2014Article
- Formation of S-Cl phosphorothioate adduct radicals in dsDNA S-oligomers: hole transfer to guanine vs disulfide anion radical formation.Journal of the American Chemical Society · 2013Article
- Hydroxyl ion addition to one-electron oxidized thymine: unimolecular interconversion of C5 to C6 OH-adducts.Journal of the American Chemical Society · 2013Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Employing electron spin resonance (ESR) spectroscopy, we have characterized the radicals formed in 3'-azido-3'-deoxythymidine (3'-AZT) and in its 5'-analog 5'-azido-5'-deoxythymidine (5'-AZT) after electron attachment in gamma-irradiated aqueous (H(2)O or D(2)O) glassy (7.5 M LiCl) systems. ESR spectral studies and theoretical calculations show that the predominant site of electron capture in 3'-AZT and in 5'-AZT is at the azide group and not at the thymine moiety. The azide group in AZT is therefore more electron affinic than the most electron affinic DNA base, thymine. Electron attachment to 3'-AZT and 5'-AZT results in an unstable azide anion radical intermediate (RN(3)*(-)) that is too short-lived to be observed in our work even at 77 K. At 77 K, we observe the neutral aminyl radical (RNH*) after loss of N(2) from RN(3)*(-) followed by protonation of nitrene anion radical (RN*(-)) to give RNH*. The expected RN*(-) intermediate is not observed as protonation from water is complete at 77 K even under highly basic conditions. Formation of RND* in D(2)O solutions confirms water as the source of the NH proton in the RNH*. Our assignments to these radicals are aided by DFT calculations for hyperfine coupling constants that closely match the experimental values. On annealing to higher temperatures (ca. 160-170 K), RNH* undergoes bimolecular hydrogen abstraction reactions from the thymine methyl group and the sugar moiety resulting in the formation of the thymine allyl radical (UCH(2)*) and two sugar radicals, C3'* and C5'*. RNH* also results in one-electron oxidation of the guanine base in 3'-AZG. This work provides a potential mechanism for the reported radiosensitization effects of AZT.
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