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New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells

Head and neck cancer (HNC) therapy is limited; therefore, new solutions are increasingly being sought among flavonoids, which exhibit numerous biological properties, including potential anticancer activity. However, because they are mostly insoluble in water, are unstable and have low bioavailabilit...

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Autores principales: Kubina, Robert, Krzykawski, Kamil, Sokal, Arkadiusz, Madej, Marcel, Dziedzic, Arkadiusz, Kadela-Tomanek, Monika
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10528839/
https://www.ncbi.nlm.nih.gov/pubmed/37759511
http://dx.doi.org/10.3390/cells12182288
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author Kubina, Robert
Krzykawski, Kamil
Sokal, Arkadiusz
Madej, Marcel
Dziedzic, Arkadiusz
Kadela-Tomanek, Monika
author_facet Kubina, Robert
Krzykawski, Kamil
Sokal, Arkadiusz
Madej, Marcel
Dziedzic, Arkadiusz
Kadela-Tomanek, Monika
author_sort Kubina, Robert
collection PubMed
description Head and neck cancer (HNC) therapy is limited; therefore, new solutions are increasingly being sought among flavonoids, which exhibit numerous biological properties, including potential anticancer activity. However, because they are mostly insoluble in water, are unstable and have low bioavailability, they are subjected to chemical modification to obtain new derivatives with better properties. This study aimed to synthesize and analyze new propargyloxy derivatives of galangin, kaempferol and fisetin, and to evaluate their anticancer activity against selected HNC cell lines. The obtained derivatives were assessed by spectroscopic analysis; next, their anticancer activity was evaluated using a flow cytometer and real-time cell analysis. The results showed that only the fisetin derivative was suitable for further analysis, due to the lack of crystal formation of the compound. The fisetin derivative statistically significantly increases the number of cells in the G2/M phase (p < 0.05) and increases cyclin B1 levels. A statistically significant increase in the number of apoptotic cells after being exposed to the tested compound was also observed (p < 0.05). The data indicate that the obtained fisetin derivative exhibits anticancer activity by affecting the cell cycle and increasing apoptosis in selected HNC lines, which suggests its potential use as a new medicinal agent in the future.
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spelling pubmed-105288392023-09-28 New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells Kubina, Robert Krzykawski, Kamil Sokal, Arkadiusz Madej, Marcel Dziedzic, Arkadiusz Kadela-Tomanek, Monika Cells Article Head and neck cancer (HNC) therapy is limited; therefore, new solutions are increasingly being sought among flavonoids, which exhibit numerous biological properties, including potential anticancer activity. However, because they are mostly insoluble in water, are unstable and have low bioavailability, they are subjected to chemical modification to obtain new derivatives with better properties. This study aimed to synthesize and analyze new propargyloxy derivatives of galangin, kaempferol and fisetin, and to evaluate their anticancer activity against selected HNC cell lines. The obtained derivatives were assessed by spectroscopic analysis; next, their anticancer activity was evaluated using a flow cytometer and real-time cell analysis. The results showed that only the fisetin derivative was suitable for further analysis, due to the lack of crystal formation of the compound. The fisetin derivative statistically significantly increases the number of cells in the G2/M phase (p < 0.05) and increases cyclin B1 levels. A statistically significant increase in the number of apoptotic cells after being exposed to the tested compound was also observed (p < 0.05). The data indicate that the obtained fisetin derivative exhibits anticancer activity by affecting the cell cycle and increasing apoptosis in selected HNC lines, which suggests its potential use as a new medicinal agent in the future. MDPI 2023-09-15 /pmc/articles/PMC10528839/ /pubmed/37759511 http://dx.doi.org/10.3390/cells12182288 Text en © 2023 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
Kubina, Robert
Krzykawski, Kamil
Sokal, Arkadiusz
Madej, Marcel
Dziedzic, Arkadiusz
Kadela-Tomanek, Monika
New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells
title New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells
title_full New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells
title_fullStr New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells
title_full_unstemmed New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells
title_short New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells
title_sort new propargyloxy derivatives of galangin, kaempferol and fisetin—synthesis, spectroscopic analysis and in vitro anticancer activity on head and neck cancer cells
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10528839/
https://www.ncbi.nlm.nih.gov/pubmed/37759511
http://dx.doi.org/10.3390/cells12182288
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