Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Coulometric Titration as a Tool to Compare the Antioxidant Capacity of Selenium and Sulfur Containing Substances and Selenocystine Mimetic Properties

Version 1 : Received: 12 June 2024 / Approved: 13 June 2024 / Online: 13 June 2024 (09:42:57 CEST)

How to cite: Poluboyarinov*, P.; Moiseeva, I.; Elistratov, D.; Glebova, N.; Mitishev, A.; Sosnovsky, E.; Kuznetsova, A. Coulometric Titration as a Tool to Compare the Antioxidant Capacity of Selenium and Sulfur Containing Substances and Selenocystine Mimetic Properties. Preprints 2024, 2024060908. https://doi.org/10.20944/preprints202406.0908.v1 Poluboyarinov*, P.; Moiseeva, I.; Elistratov, D.; Glebova, N.; Mitishev, A.; Sosnovsky, E.; Kuznetsova, A. Coulometric Titration as a Tool to Compare the Antioxidant Capacity of Selenium and Sulfur Containing Substances and Selenocystine Mimetic Properties. Preprints 2024, 2024060908. https://doi.org/10.20944/preprints202406.0908.v1

Abstract

Sulfur and selenium-containing organic compounds (amino acids and xenobiotics) have received interests as potential medicines, sources of the selenium and antioxidants. The purpose of the study was to comparatively investigate the antioxidant capacity of sulfur- and selenium-containing amino acids, xenobiotics and the study of possible mimetic properties of selenocystine. To evaluate the antioxidant capacity, coulometric oxidation with electrogenerated bromine was used. Methionine, cystine and selenocystine react with bromine quickly and quantitatively. Diacetophenonyl selenide, ebselen and selenopyran are oxidized nonstoichiometrically, but show high antioxidant capacity. We hypothesized that selenium xenobiotcs might be exert prolonged antioxidant effect. Conditions have been optimized to determine antioxidant capacity of selenium and sulfur substances in water and methanol. We proposed theory and reactions schemes for the interaction of bromine with methionine, cystine, selenocystine diacetophenonylselenide, ebselen, thiopyran and selenopyran. Antioxidant capacities in both water and methanol decrease in the following order: L-cystine > L-selenocystine > methionine. Sulfur-containing substances in methanol show higher antioxidant capacity than selenium-containing antioxidants. Among selenium-containing xenobiotics, DAPS shows the highest antioxidant capacity (comparable to cystine). Selenopyran and ebselen are less active as antioxidants. Diselenide bond is a selenocystin chromophore for its UV-assay. For the first time we demonstrated the ability of selenocystine to be actively involved in redox reactions and to act as a mimetic, a low-molecular-weight analogue of glutathione peroxidase.

Keywords

antioxidant capacity; coulometic titration; sulfur-containing; selenium-containing amino acids; xenobiotics; mimetics

Subject

Chemistry and Materials Science, Electrochemistry

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