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

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...

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Autores principales: Obieziurska, Magdalena, Pacuła, Agata J., Laskowska, Anna, Długosz-Pokorska, Angelika, Janecka, Anna, Ścianowski, Jacek
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7040810/
https://www.ncbi.nlm.nih.gov/pubmed/32024274
http://dx.doi.org/10.3390/ma13030661
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author Obieziurska, Magdalena
Pacuła, Agata J.
Laskowska, Anna
Długosz-Pokorska, Angelika
Janecka, Anna
Ścianowski, Jacek
author_facet Obieziurska, Magdalena
Pacuła, Agata J.
Laskowska, Anna
Długosz-Pokorska, Angelika
Janecka, Anna
Ścianowski, Jacek
author_sort Obieziurska, Magdalena
collection PubMed
description 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.
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spelling pubmed-70408102020-03-09 Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability Obieziurska, Magdalena Pacuła, Agata J. Laskowska, Anna Długosz-Pokorska, Angelika Janecka, Anna Ścianowski, Jacek Materials (Basel) Article 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. MDPI 2020-02-02 /pmc/articles/PMC7040810/ /pubmed/32024274 http://dx.doi.org/10.3390/ma13030661 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Obieziurska, Magdalena
Pacuła, Agata J.
Laskowska, Anna
Długosz-Pokorska, Angelika
Janecka, Anna
Ścianowski, Jacek
Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
title Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
title_full Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
title_fullStr Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
title_full_unstemmed Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
title_short Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
title_sort seleninic acid potassium salts as water-soluble biocatalysts with enhanced bioavailability
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7040810/
https://www.ncbi.nlm.nih.gov/pubmed/32024274
http://dx.doi.org/10.3390/ma13030661
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