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Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound

Pharmacological and nutraceutical effects of isoflavones, which include genistein (GE), are attributed to their antioxidant activity protecting cells against carcinogenesis. The knowledge of the oxidation mechanisms of an active substance is crucial to determine its pharmacological properties. The a...

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Autores principales: Stolarczyk, Elżbieta U., Strzempek, Weronika, Łaszcz, Marta, Leś, Andrzej, Menaszek, Elżbieta, Sidoryk, Katarzyna, Stolarczyk, Krzysztof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8395759/
https://www.ncbi.nlm.nih.gov/pubmed/34445486
http://dx.doi.org/10.3390/ijms22168783
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author Stolarczyk, Elżbieta U.
Strzempek, Weronika
Łaszcz, Marta
Leś, Andrzej
Menaszek, Elżbieta
Sidoryk, Katarzyna
Stolarczyk, Krzysztof
author_facet Stolarczyk, Elżbieta U.
Strzempek, Weronika
Łaszcz, Marta
Leś, Andrzej
Menaszek, Elżbieta
Sidoryk, Katarzyna
Stolarczyk, Krzysztof
author_sort Stolarczyk, Elżbieta U.
collection PubMed
description Pharmacological and nutraceutical effects of isoflavones, which include genistein (GE), are attributed to their antioxidant activity protecting cells against carcinogenesis. The knowledge of the oxidation mechanisms of an active substance is crucial to determine its pharmacological properties. The aim of the present work was to explain complex oxidation processes that have been simulated during voltammetric experiments for our new thiolated genistein analog (TGE) that formed the self-assembled monolayer (SAM) on the gold electrode. The thiol linker assured a strong interaction of sulfur nucleophiles with the gold surface. The research comprised of the study of TGE oxidative properties, IR-ATR, and MALDI-TOF measurements of SAM before and after electrochemical oxidation. TGE has been shown to be electrochemically active. It undergoes one irreversible oxidation reaction and one quasi-reversible oxidation reaction in PBS buffer at pH 7.4. The oxidation of TGE results in electroactive products composed likely from TGE conjugates (e.g., trimers) as part of polymer. The electroactive centers of TGE and its oxidation mechanism were discussed using IR supported by quantum chemical and molecular mechanics calculations. Preliminary in-vitro studies indicate that TGE exhibits higher cytotoxic activity towards DU145 human prostate cancer cells and is safer for normal prostate epithelial cells (PNT2) than genistein itself.
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spelling pubmed-83957592021-08-28 Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound Stolarczyk, Elżbieta U. Strzempek, Weronika Łaszcz, Marta Leś, Andrzej Menaszek, Elżbieta Sidoryk, Katarzyna Stolarczyk, Krzysztof Int J Mol Sci Article Pharmacological and nutraceutical effects of isoflavones, which include genistein (GE), are attributed to their antioxidant activity protecting cells against carcinogenesis. The knowledge of the oxidation mechanisms of an active substance is crucial to determine its pharmacological properties. The aim of the present work was to explain complex oxidation processes that have been simulated during voltammetric experiments for our new thiolated genistein analog (TGE) that formed the self-assembled monolayer (SAM) on the gold electrode. The thiol linker assured a strong interaction of sulfur nucleophiles with the gold surface. The research comprised of the study of TGE oxidative properties, IR-ATR, and MALDI-TOF measurements of SAM before and after electrochemical oxidation. TGE has been shown to be electrochemically active. It undergoes one irreversible oxidation reaction and one quasi-reversible oxidation reaction in PBS buffer at pH 7.4. The oxidation of TGE results in electroactive products composed likely from TGE conjugates (e.g., trimers) as part of polymer. The electroactive centers of TGE and its oxidation mechanism were discussed using IR supported by quantum chemical and molecular mechanics calculations. Preliminary in-vitro studies indicate that TGE exhibits higher cytotoxic activity towards DU145 human prostate cancer cells and is safer for normal prostate epithelial cells (PNT2) than genistein itself. MDPI 2021-08-16 /pmc/articles/PMC8395759/ /pubmed/34445486 http://dx.doi.org/10.3390/ijms22168783 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Stolarczyk, Elżbieta U.
Strzempek, Weronika
Łaszcz, Marta
Leś, Andrzej
Menaszek, Elżbieta
Sidoryk, Katarzyna
Stolarczyk, Krzysztof
Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound
title Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound
title_full Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound
title_fullStr Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound
title_full_unstemmed Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound
title_short Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound
title_sort anti-cancer and electrochemical properties of thiogenistein—new biologically active compound
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8395759/
https://www.ncbi.nlm.nih.gov/pubmed/34445486
http://dx.doi.org/10.3390/ijms22168783
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