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...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-09-01
|
| Series: | Cells |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4409/12/18/2288 |
| _version_ | 1797580782357708800 |
|---|---|
| author | Robert Kubina Kamil Krzykawski Arkadiusz Sokal Marcel Madej Arkadiusz Dziedzic Monika Kadela-Tomanek |
| author_facet | Robert Kubina Kamil Krzykawski Arkadiusz Sokal Marcel Madej Arkadiusz Dziedzic Monika Kadela-Tomanek |
| author_sort | Robert Kubina |
| collection | DOAJ |
| 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 (<i>p</i> < 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 (<i>p</i> < 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. |
| first_indexed | 2024-03-10T22:55:53Z |
| format | Article |
| id | doaj.art-0506fbe7bfd1450781a1e7ce979304ab |
| institution | Directory Open Access Journal |
| issn | 2073-4409 |
| language | English |
| last_indexed | 2024-03-10T22:55:53Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Cells |
| spelling | doaj.art-0506fbe7bfd1450781a1e7ce979304ab2023-11-19T09:59:57ZengMDPI AGCells2073-44092023-09-011218228810.3390/cells12182288New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer CellsRobert Kubina0Kamil Krzykawski1Arkadiusz Sokal2Marcel Madej3Arkadiusz Dziedzic4Monika Kadela-Tomanek5Department of Pathology, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Ostrogórska 30, 41-200 Sosnowiec, PolandSilesia LabMed, Centre for Research and Implementation, Medical University of Silesia in Katowice, 18 Medyków Str., 40-752 Katowice, PolandStudents Scientific Group of Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, 41-200 Sosnowiec, PolandSilesia LabMed, Centre for Research and Implementation, Medical University of Silesia in Katowice, 18 Medyków Str., 40-752 Katowice, PolandDepartment of Conservative Dentistry with Endodontics, Medical University of Silesia, 40-055 Katowice, PolandDepartment of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, 41-200 Sosnowiec, PolandHead 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 (<i>p</i> < 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 (<i>p</i> < 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.https://www.mdpi.com/2073-4409/12/18/2288flavonolanticancerflow cytometryapoptosishead and neck cancercyclin |
| spellingShingle | Robert Kubina Kamil Krzykawski Arkadiusz Sokal Marcel Madej Arkadiusz Dziedzic Monika Kadela-Tomanek New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin—Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells Cells flavonol anticancer flow cytometry apoptosis head and neck cancer cyclin |
| 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 | flavonol anticancer flow cytometry apoptosis head and neck cancer cyclin |
| url | https://www.mdpi.com/2073-4409/12/18/2288 |
| work_keys_str_mv | AT robertkubina newpropargyloxyderivativesofgalanginkaempferolandfisetinsynthesisspectroscopicanalysisandinvitroanticanceractivityonheadandneckcancercells AT kamilkrzykawski newpropargyloxyderivativesofgalanginkaempferolandfisetinsynthesisspectroscopicanalysisandinvitroanticanceractivityonheadandneckcancercells AT arkadiuszsokal newpropargyloxyderivativesofgalanginkaempferolandfisetinsynthesisspectroscopicanalysisandinvitroanticanceractivityonheadandneckcancercells AT marcelmadej newpropargyloxyderivativesofgalanginkaempferolandfisetinsynthesisspectroscopicanalysisandinvitroanticanceractivityonheadandneckcancercells AT arkadiuszdziedzic newpropargyloxyderivativesofgalanginkaempferolandfisetinsynthesisspectroscopicanalysisandinvitroanticanceractivityonheadandneckcancercells AT monikakadelatomanek newpropargyloxyderivativesofgalanginkaempferolandfisetinsynthesisspectroscopicanalysisandinvitroanticanceractivityonheadandneckcancercells |