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Open AccessFeature PaperArticle

Converging Fate of the Oxidation and Reduction of 8-Thioguanosine

1
Adam Mickiewicz University, Faculty of Chemistry, Wieniawskiego 1, 61-712 Poznań, Poland
2
R&D Laboratory, Lipinutragen srl, Via Piero Gobetti 101, 40129 Bologna, Italy
3
ISOF, Consiglio Nazionale delle Ricerche, Via Piero Gobetti 101, 40129 Bologna, Italy
4
Universidad de Buenos Aires, Facultad de Farmacia y Bioquimíca, Departamento de Quimíca Organíca, Junin 954, RA-1113 Buenos Aires, Argentina
5
Center of Advanced Technologies, Adam Mickiewicz University, 61-712 Poznań, Poland
*
Author to whom correspondence should be addressed.
These authors contributed equally to the work.
Academic Editor: Derek J. McPhee
Molecules 2019, 24(17), 3143; https://doi.org/10.3390/molecules24173143
Received: 2 August 2019 / Revised: 27 August 2019 / Accepted: 28 August 2019 / Published: 29 August 2019
(This article belongs to the Special Issue Biomimetic Radical Chemistry and Applications)
Thione-containing nucleobases have attracted the attention of the scientific community for their application in oncology, virology, and transplantology. The detailed understanding of the reactivity of the purine derivative 8-thioguanosine (8-TG) with reactive oxygen species (ROS) and free radicals is crucial for its biological relevance. An extensive investigation on the fate of 8-TG under both reductive and oxidative conditions is here reported, and it was tested by employing steady-state photooxidation, laser flash photolysis, as well as γ-radiolysis in aqueous solutions. The characterization of the 8-TG T1 excited state by laser flash photolysis and the photooxidation experiments confirmed that singlet oxygen is a crucial intermediate in the formation of the unexpected reduced product guanosine, without the formation of the usual oxygenated sulfinic or sulfonic acids. Furthermore, a thorough screening of different radiolytic conditions upon γ-radiation afforded the reduced product. These results were rationalized by performing control experiments in the predominant presence of each reactive species formed by radiolysis of water, and the mechanistic pathway scenario was postulated on these bases. View Full-Text
Keywords: photolysis; laser flash photolysis; γ-radiolysis; singlet oxygen; nucleosides; free radicals; reaction mechanism photolysis; laser flash photolysis; γ-radiolysis; singlet oxygen; nucleosides; free radicals; reaction mechanism
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MDPI and ACS Style

Taras-Goslinska, K.; Vetica, F.; Barata-Vallejo, S.; Triantakostanti, V.; Marciniak, B.; Chatgilialoglu, C. Converging Fate of the Oxidation and Reduction of 8-Thioguanosine. Molecules 2019, 24, 3143.

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