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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2021
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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. |
format | Online Article Text |
id | pubmed-8395759 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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