Solubility of Curcumin in Water and Aqueous Solutions of Tetradecyltriphenylphosphonium Bromide with Formation of Protomicelles

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Abstract

By spectrophotometry studied the interaction of curcumin, a biologically important molecule, with tetradecyltriphenylphosphonium bromide in an aqueous environment depending on the concentration of surfactants in the premicellar and micellar ranges. Experiments were carried out with saturated solutions of curcumin under conditions of thermodynamic equilibrium of the solution with the dye precipitate. The solubility of curcumin in water has been clarified (about 2 µM). It has been shown that the process of solubilization of curcumin begins in the premicellar region of surfactants, is enhanced in the presence of adsorption protomicelles, but is most effective in the presence of ordinary micelles. The extinction coefficients of curcumin monomers in dimethyl sulfoxide, water and micellar solutions are determined. Based on experimental data, the limiting value of the solubilization capacity tetradecyltriphenylphosphonium bromide with respect to curcumin is calculated. The conductometry was used to determine the values of the critical micelle concentration (CMC) of the studied surfactant in the presence and absence of curcumin and confirm the theoretical conclusion that the CMC of the surfactants is reduced by the solubilizate.

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About the authors

T. G. Movchan

Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Author for correspondence.
Email: movchan_tamara@mail.ru
ORCID iD: 0000-0001-6249-6732
Russian Federation, Moscow, 119071

A. I. Rusanov

Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences; Saint Petersburg State University

Email: movchan_tamara@mail.ru
ORCID iD: 0000-0002-8972-1220
Russian Federation, Moscow, 119071; Saint Petersburg, 199034

E. V. Plotnikova

Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Email: movchan_tamara@mail.ru
ORCID iD: 0000-0002-3265-3917
Russian Federation, Moscow, 119071

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Supplementary files

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2. Scheme 1.

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3. Fig. 1. Absorption spectra of curcumin in DMSO solutions at optical path length (l) of 1 cm and drug concentrations c2 = 1.5 (1), 3.6 (2), 5.5 (3), 10.6 (4) and 19.3 μM (5).

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4. Fig. 2. Absorption spectra of aqueous solutions of curcumin at concentrations of the drug c2, μM: (a) 1.3 (1 and its components at decomposition 11 and 12); (b) 8 (2), 11 (3), 13.8 (4) and 23 (5). DMSO content, wt %: 0.019 (1), 0.066 (2), 0.092 (3), 0.198 (4) и 0.35 (5). l = 1 cm.

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5. Fig. 3. Concentration dependence of the electrical conductivity κ(c1) of aqueous solutions of TDPPB: (a) without curcumin (curves 1 and 2), (b) in the presence of curcumin (1-3).

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6. Fig. 4. Absorption spectra of curcumin in samples of aqueous dye system (a) with 2 (1), 7 (2), 9 (3) and 21 days (4) exposure; decomposition of spectrum 1 into components 11 and 12 (b). l = 1 cm.

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7. Fig. 5. Absorption spectra of aqueous saturated solution of curcumin in the presence of TDPPB at concentrations of c1, mM: (a) 0. 1 (1), 0.18 (2), 0.25 (3) and 0.29 (4); (b) 0.36 (1), 0.4 (2), 0.44 (3), 0.5 (4) and 0.6 (5) at l = 1 cm; (c) 0.75 (1), 0.96 (2), 1.3 (3) and 1.9 (4) at l = 0.2 cm.

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8. Fig. 6. Dependence of optical density (A / l) at l = 1 cm on the c1 concentration of TDTFPB in saturated curcumin solution in the intervals c1 = 0.1-0.5 (a) and 0.1-2 mM (b).

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9. Fig. 7. Absorption spectra of curcumin in 1.9 mM TDPPB solutions at c2 drug concentrations, μM: 2.6 (1), 5.1 (2), 10 (3), 15 (4), 20 (5) at l = 1 cm.

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