ArticleMolecules (Basel, Switzerland)2019
Why Does the Type of Halogen Atom Matter for the Radiosensitizing Properties of 5-Halogen Substituted 4-Thio-2'-Deoxyuridines?
Article in Molecules (Basel, Switzerland), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 16 citations in OpenAlex.
- Substituted benzylamino-2'-deoxyadenosine a modified nucleoside with radiosensitizing properties.Scientific reports · 2025Article
- Surprising Radiolytic Stability of 8-Thiomethyladenine in an Aqueous Solution.The journal of physical chemistry. B · 2024Article
- Dissociative Electron Attachment to 5-Iodo-4-thio-2'-deoxyuridine: A Potential Radiosensitizer of Hypoxic Cells.The journal of physical chemistry letters · 2023Article
- Electron-Induced Decomposition of 5-Bromo-4-thiouracil and 5-Bromo-4-thio-2'-deoxyuridine: The Effect of the Deoxyribose Moiety on Dissociative Electron Attachment.International journal of molecular sciences · 2023Article
- Biomimetic Radical Chemistry and Applications.Molecules (Basel, Switzerland) · 2022Article
- Influence of Hypoxia on Radiosensitization of Cancer Cells by 5-Bromo-2'-deoxyuridine.International journal of molecular sciences · 2022Article
- Application of Radiosensitizers in Cancer Radiotherapy.International journal of nanomedicine · 2021Review
- Uracil-5-ylThe journal of physical chemistry. B · 2020Article
- Radiation Induced One-Electron Oxidation of 2-Thiouracil in Aqueous Solutions.Molecules (Basel, Switzerland) · 2019Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Radiosensitizing properties of substituted uridines are of great importance for radiotherapy. Very recently, we confirmed 5-iodo-4-thio-2'-deoxyuridine (ISdU) as an efficient agent, increasing the extent of tumor cell killing with ionizing radiation. To our surprise, a similar derivative of 4-thio-2'-deoxyuridine, 5-bromo-4-thio-2'-deoxyuridine (BrSdU), does not show radiosensitizing properties at all. In order to explain this remarkable difference, we carried out a radiolytic (stationary and pulse) and quantum chemical studies, which allowed the pathways to all radioproducts to be rationalized. In contrast to ISdU solutions, where radiolysis leads to 4-thio-2'-deoxyuridine and its dimer, no dissociative electron attachment (DEA) products were observed for BrSdU. This observation seems to explain the lack of radiosensitizing properties of BrSdU since the efficient formation of the uridine-5-yl radical, induced by electron attachment to the modified nucleoside, is suggested to be an indispensable attribute of radiosensitizing uridines. A larger activation barrier for DEA in BrSdU, as compared to ISdU, is probably responsible for the closure of DEA channel in the former system. Indeed, besides DEA, the XSdU anions may undergo competitive protonation, which makes the release of X
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