Quantum-chemical modeling of the optimal geometries of naringenin, apigenin, and menadione was performed. Their electronic properties and interactions with artificial liposomal membranes were evaluated using fluorescence probe spectroscopy. The studied flavonoids and quinone interacted strongly with 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine liposomal membranes according to the fluorescence analysis. The fluorescent probes TMA–DPH and DPH incorporated in the lipid bilayer were used to show that apigenin and naringenin (5–50 μM) and menadione (50 μM) decreased the microfluidity of the liposomal membrane bilayer at different depths with apigenin (but not menadione and naringenin) effectively quenching the fluorescence of TMA–DPH and DPH. Interaction of the studied compounds with the membranes depended on the polarity, volume, geometry, and water solubility of the molecules. The probe Laurdan was used to show that naringenin and apigenin dose-dependently converted the bilayer into a more ordered state while apigenin decreased the ordering of the lipid packing and increased the hydration near the polar head groups due to incorporation of the effectors into the liposomes. The torsion angle between the rings of the planar menadione and apigenin molecules was 180° while that of naringenin was 86.4°. Cranberry flavonoid glycosides (25–50 μg/mL) slightly increased the microfluidity of the liposomal membrane near the polar head groups of the phospholipids.
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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 90, No. 3, pp. 415–422, May–June, 2023.
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Veiko, A.G., Lapshina, E.A., Yukhnevich, H.G. et al. Study of the Interaction of Naringenin, Apigenin, and Menadione with Membranes using Fluorescent Probes and Quantum Chemistry. J Appl Spectrosc 90, 535–542 (2023). https://doi.org/10.1007/s10812-023-01564-0
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DOI: https://doi.org/10.1007/s10812-023-01564-0