ArticleRSC advances2018
5-Selenocyanato and 5-trifluoromethanesulfonyl derivatives of 2'-deoxyuridine: synthesis, radiation and computational chemistry as well as cytotoxicity.
Article in RSC advances, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 21 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
- Substituted benzylamino-2'-deoxyadenosine a modified nucleoside with radiosensitizing properties.Scientific reports · 2025Article
- Dissociative Electron Attachment to 5-Iodo-4-thio-2'-deoxyuridine: A Potential Radiosensitizer of Hypoxic Cells.The journal of physical chemistry letters · 2023Article
- Review
- Why 6-Iodouridine Cannot Be Used as a Radiosensitizer of DNA Damage? Computational and Experimental Studies.The journal of physical chemistry. B · 2023Article
- Inactive-to-Active Transition of Human Thymidine Kinase 1 Revealed by Molecular Dynamics Simulations.Journal of chemical information and modeling · 2022Article
- Quasi-Free Electron-Mediated Radiation Sensitization by C5-Halopyrimidines.The journal of physical chemistry. A · 2021Article
- Low-Energy Electron Damage to Condensed-Phase DNA and Its Constituents.International journal of molecular sciences · 2021Review
- 5-(International journal of molecular sciences · 2020Article
- Uracil-5-ylThe journal of physical chemistry. B · 2020Article
- Reaction of Electrons with DNA: Radiation Damage to Radiosensitization.International journal of molecular sciences · 2019Review
- Why Does the Type of Halogen Atom Matter for the Radiosensitizing Properties of 5-Halogen Substituted 4-Thio-2'-Deoxyuridines?Molecules (Basel, Switzerland) · 2019Article
Corrections and comments
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Authors and funding
9 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
5-Selenocyanato-2'-deoxyuridine (SeCNdU) and 5-trifluoromethanesulfonyl-2'-deoxyuridine (OTfdU) have been synthesized and their structures have been confirmed with NMR and MS methods. Both compounds undergo dissociative electron attachment (DEA) when irradiated with X-rays in an aqueous solution containing a hydroxyl radical scavenger. The DEA yield of SeCNdU significantly exceeds that of 5-bromo-2'-deoxyuridine (BrdU), remaining in good agreement with the computationally revealed profile of electron-induced degradation. The radiolysis products indicate, in line with theoretical predictions, Se-CN bond dissociation as the main reaction channel. On the other hand, the DEA yield for OTfdU is slightly lower than the degradation yield measured for BrdU, despite the fact that the calculated driving force for the electron-induced OTfdU dissociation substantially overpasses the thermodynamic stimulus for BrdU degradation. Moreover, the calculated DEA profile suggests that the electron attachment induced formation of 5-hydroxy-2'-deoxyuridine (OHdU) from OTfdU, while 2'-deoxyuridine (dU) is mainly observed experimentally. We explained this discrepancy in terms of the increased acidity of OTfdU resulting in efficient deprotonation of the N3 atom, which brings about the domination of the OTfdU(N3-H)
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