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V. M. Barvinchenko and N. O. Lipkovska
Solubilization and Tautomeric Transformations of Natural Curcumin Dye into Aqueous Solution of Cationic Dimeric Surfactant Decamethoxine
0777–0789 (2022)

PACS numbers: 31.70.Dk, 64.75.Bc, 64.75.Yz, 78.40.Me, 82.70.Uv, 87.85.Qr, 87.85.Rs

The solubilization of the natural dye curcumin in water in the presence of cationic dimeric surfactant decamethoxine (DCM) is investigated by UV–Vis spectrophotometry. As shown experimentally, the solubility of curcumin increases linearly, when the concentration of decamethoxine exceeds the value of 8·10-3 M, which corresponds to the critical concentration of micelle formation for this cationic surfactant. The solubilization efficiency is quantitatively characterized by the solubilization capacity of decamethoxine with respect to curcumin and the binding constant. Comparison of the absorption spectra of tautomeric forms of curcumin in the decamethoxine nanosystems with the corresponding spectra in aqueous–ethanolic solutions with known dielectric constant shows that this dye could be a spectral probe to determine the effective dielectric constant of pseudo-phases inside the micelles. As found, the ketone form of curcumin predominates in aqueous solutions, while, in an organized medium formed by nanosize micellar aggregates, curcumin is only in the enol form. Based on the structure of the curcumin molecule, which contains polar (phenolic and ketone groups) and nonpolar (hydrocarbon and aromatic) fragments, as well as on the basis of experimental data, the most likely site of curcumin in the organized solution is the intermediate palisade layer of decamethoxine micelles. The obtained results can be used primarily in solving biomedical problems, as they open the possibility of creation of new, more effective preparations of curcumin, capable of providing its high solubility in the water medium, and, accordingly, increasing bioavailability.

Key words: curcumin, decamethoxine, spectrophotometry, solubilization, keto-enol tautomerism.

https://doi.org/10.15407/nnn.20.03.777

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