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Open AccessArticle

Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability

1
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
2
Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland
*
Author to whom correspondence should be addressed.
Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70th birthday.
Materials 2020, 13(3), 661; https://doi.org/10.3390/ma13030661
Received: 20 December 2019 / Revised: 16 January 2020 / Accepted: 31 January 2020 / Published: 2 February 2020
Organoselenium compounds are well-known glutathione peroxidase (GPx) mimetics that possess antioxidants/prooxidant properties and are able to modulate the concentration of reactive oxygen species (ROS), preventing oxidative stress in normal cells or inducing ROS formation in cancer cells leading to apoptosis. The purpose of this study was the synthesis of potent GPx mimics with antioxidant and anticancer activity along with improved bioavailability, as a result of good solubility in protic solvents. As a result of our research, glutathione peroxidase (GPx) mimetics in the form of water-soluble benzeneseleninic acid salts were obtained. The procedure was based on the synthesis of 2-(N-alkylcarboxyamido)benzeneselenenic acids, through the oxidation of benzisoselenazol-3(2H)-ones or analogous arenediselenides with an amido group, which were further converted to corresponding potassium salts by the treatment with potassium tert-butanolate. All derivatives were tested as potential antioxidants and anticancer agents. The areneseleninic acid salts were significantly better peroxide scavengers than analogous acids and the well-known organoselenium antioxidant ebselen. The highest activity was observed for the 2-(N-ethylcarboxyamido)benzeneselenenic acid potassium salt. The strongest cytotoxic effect against breast cancer (MCF-7) and human promyelocytic leukemia (HL-60) cell lines was found for 2-(N-cyclohexylcarboxyamido)benzeneselenenic acid potassium salt and the 2-(N-ethylcarboxyamido)benzeneselenenic acid, respectively. The structure–activity correlations, including the differences in reactivity of benzeneseleninic acids and corresponding salts were evaluated. View Full-Text
Keywords: areneseleninic acids; areneseleninic acid salts; amphiphilic compounds; antioxidant activity; antiproliferative activity areneseleninic acids; areneseleninic acid salts; amphiphilic compounds; antioxidant activity; antiproliferative activity
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Obieziurska, M.; Pacuła, A.J.; Laskowska, A.; Długosz-Pokorska, A.; Janecka, A.; Ścianowski, J. Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability. Materials 2020, 13, 661.

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