Surprising Radiolytic Stability of 8‑Thiomethyladenine in an Aqueous Solution

Magdalena Datta; Adrian Szczyrba; Magdalena Zdrowowicz; Dariusz Wyrzykowski; Olga Ciupak; Sebastian Demkowicz; Farhad Izadi; Stephan Denifl; Janusz Rak

doi:10.1021/acs.jpcb.4c01033

Surprising Radiolytic Stability of 8‑Thiomethyladenine in an Aqueous Solution

Abstract

8-Thiomethyladenine (ASCH3), a potentially radiosensitizing modified nucleobase, has been synthesized in a reaction between 8-thioadenine and methyl iodide. Despite favorable dissociative electron attachment (DEA) characteristics, the radiolysis of an aqueous solution of ASCH3 with a dose of X-ray amounting to as much as 300 Gy leads to no effects. Nevertheless, crossed electron-molecule beam experiments in the gas phase on ASCH3 confirm the theoretical findings regarding the stability of its radical anion, namely, the most abundant reaction channel is related to the dissociation of the S-CH3 bond in the respective anion. Furthermore, electroninduced degradation of ASCH3 has been observed in aprotic acetonitrile, which is strong evidence for the involvement of proton transfer (PT) in stabilizing the radical anion in an aqueous solution. These findings demonstrate that PT in water can be the main player in deciding the radiosensitizing properties of modified nucleobases/nucleosides.

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Authors (9)

Magdalena Datta mgr inż.
- Uniwersytet Gdański
Adrian Szczyrba
- Uniwersytet Gdański
Magdalena Zdrowowicz
- Uniwersytet Gdański
Dariusz Wyrzykowski
- Uniwersytet Gdański
Olga Ciupak mgr inż.
Sebastian Demkowicz dr hab. inż.
Farhad Izadi
- Uniwersytet w Innsbruck
Stephan Denifl
- Uniwersytet w Innsbruck
Janusz Rak Prof.
- Uniwersytet Gdański

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DOI:: Digital Object Identifier (open in new tab) 10.1021/acs.jpcb.4c01033
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Articles

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artykuły w czasopismach dostępnych w wersji elektronicznej [także online]

Published in:

JOURNAL OF PHYSICAL CHEMISTRY B pages 3621 - 3630,
ISSN: 1520-6106

Language:

English

Publication year:

2024

Bibliographic description:

Datta M., Szczyrba A., Zdrowowicz M., Wyrzykowski D., Ciupak O., Demkowicz S., Izadi F., Denifl S., Rak J., Surprising Radiolytic Stability of 8‑Thiomethyladenine in an Aqueous Solution, JOURNAL OF PHYSICAL CHEMISTRY B, 2024,10.1021/acs.jpcb.4c01033

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