Halochromic Behavior and Anticancer Effect of New Synthetic Anthocyanidins Complexed with β-Cyclodextrin Derivatives
| Autor: | Iulia Păușescu, Izolda Kántor, György Babos, Zoltán May, Andrea Fodor-Kardos, Zsombor Miskolczy, László Biczók, Francisc Péter, Mihai Medeleanu, Tivadar Feczkó |
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| Rok vydání: | 2022 |
| Předmět: |
Organic Chemistry
General Medicine Cytostatic Agents anthocyanidins flavylium cytostatic effect inclusion complex β-cyclodextrin derivatives Catalysis Computer Science Applications Anthocyanins Inorganic Chemistry Chalcone Cations Spectroscopy Fourier Transform Infrared Physical and Theoretical Chemistry Molecular Biology Spectroscopy |
| Zdroj: | International Journal of Molecular Sciences; Volume 23; Issue 15; Pages: 8103 |
| ISSN: | 1422-0067 |
| Popis: | Anthocyanidins, the aglycons of anthocyanins, are known, beyond their function in plants, also as compounds with a wide range of biological and pharmacological activities, including cytostatic effect against various cancer cells. The nature and position of the substituents in the flavylium cation is essential for such biological properties, as well as the equilibrium between the multistate of the different chemical species that are generated by the flavylium cation, including quinoidal base, hemiketal, and cis- and trans-chalcones. In this work, eight new flavylium derivatives were synthesized, characterized for confirmation of the structure by FT-IR and 2D-NMR, and investigated in vitro as possible cytostatic compounds against HCT116 and HepG2 cancer cells. The most active two compounds were explored for their halochromic properties that can influence the biological activity and subjected to molecular encapsulation in β-cyclodextrin derivatives in order to increase their solubility in water and bioavailability. The anticancer effect was influenced by the position (6-, 7-, or 8-) of the methoxy group in the β-ring of the methoxy-4′-hydroxy-3′-methoxyflavylium cation, while the study of the halochromic properties revealed the important role played by the chalcone species of the pH-dependent multistate in both the uncomplexed and inclusion complex forms of these anthocyanidins. |
| Databáze: | OpenAIRE |
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