Effect of cationic Gemini surfactants ethonium and decamethoxin on the spectral properties, solubility and tautomerism of the curcumin

• Published in: Journal of surfactants and detergents 2024-07, Vol.27 (4), p.633-642
• Main Authors: Barvinchenko, Valentyna M., Kazakova, Olga O., Lipkovska, Natalia O.
• Format: Article
• Language: English
• Subjects: cationic Gemini surfactants; curcumin; keto‐enol tautomerism; solubility; spectral properties
• ISSN: 1097-3958; 1558-9293
• DOI: 10.1002/jsde.12756

The properties of natural polyphenol curcumin in water solutions of cationic Gemini surfactants decamethoxin and ethonium, which have similar positively charged nitrogen hydrophilic head groups but different spacer sizes and lengths of hydrophobic tails have been investigated in a wide range of concentrations by using UV–Vis spectroscopy and quantum‐chemical calculations. It was found that curcumin dissolves in the organized micellar media of these surfactants in the enol tautomeric form and its solubility increases 400 times compared to water. The binding constants of curcumin with decamethoxin and ethonium were determined by the solubility method. Significant differences in the influence of premicellar concentrations of cationic Gemini surfactants on the solubility and tautomeric transformations of curcumin were revealed. In contrast to decamethoxin, ethonium at a concentration below the CMC promotes a significant increase in the solubility of curcumin and a shift in the tautomeric equilibrium towards the formation of its keto form.