Solubility temperature and solvent dependence and preferential solvation of citrus flavonoid naringin in aqueous DMSO mixtures: an experimental and molecular dynamics simulation study

Abstract

This study describes the thermodynamics of dissolution of flavonoid naringin in different aqueous solutions of dimethyl sulfoxide (DMSO) containing 0-100% (w/w) under atmospheric pressure and over a temperature range of 298.15 to 325.15 K. The temperature dependence of solubility of naringin was analyzed using the modified Apelblat equation model, ideal model, and the lH equation model. In a mean harmonic temperature, the dissolution thermodynamic parameters of naringin containing DG sol , DH sol and DS sol were also calculated. Furthermore, the effects of solvent composition on the solubility of this flavonoid were analyzed in terms of Hildebrand's solubility parameter (d H ) and Kamlet, Abboud and Taft (KAT) solvatochromic parameters (a, b, and p*). Finally, the preferential solvation parameters of the flavonoid naringin by DMSO (dx DMSO,S ) were determined from experimental solubility data using the inverse Kirkwood-Buff integrals (IKBIs). It was found that water preferentially solvates naringin in waterrich mixtures while DMSO forms local solvation shells in compositions from 50% (w/w) or x DMSO ¼ 0.19 up to pure co-solvent. Moreover, the structure of solvation shells of naringin in the under study mixtures was obtained by molecular dynamics (MD) simulations. The computational results showed that in the compositions x DMSO > 0.20, the probability of presence of the DMSO molecules in vicinity of naringin is more than water molecules. These findings are compatible with the available IKBI data.

Thermodynamic modelling of solubility and preferential solvation for ribavirin (II) in co-solvent mixtures of (methanol, n -propanol, acetonitrile or 1,4-dioxane) + water

“…Accordingly, for all distances r > r cor up to infinite, the value of the integral is essentially zero. The preferential solvation parameter of ribavirin (compound 3) by the solvent (compound 1) in solvent (1) + water (2) mixtures is defined as [5][6][7][26][27][28][29][30]:…”

“…Because of the dependence of j T on composition, this term is not known for all the systems investigated. In addition, due to the minor contribution of RTj T to the inverse Kirkwood-Buff integral, the dependence of j T upon composition can be calculated approximated as an additive property by using the mixture compositions and the reported values for neat solvents by [5,6,[26][27][28][29][30]: D tr G 0 3;2!1þ2 ¼ RT ln…”

“…Because no partial molar volumes of ribavirin (3) in these mixtures are acquired in the literature, in this work this property is considered as similar to that for the pure compound as a good approximation [26][27][28][29][30]. In this way, the molar volume of ribavirin (3) is calculated by using Advanced Chemistry Development (ACD/ Labs) Software V 11.02 (sc1994-2016 ACD/Labs) as 117.0 cm 3 Ámol -1 .…”

“…Although several theoretical and semi-empirical models have employed to predict drug solubility in solvent mixtures, the availability of experimental data is still fundamental for the pharmaceutical scientists [1,25]. It is well-known that solvent mixtures has been widely used in pharmacies long ago [1][2][3][4], only recently the mechanisms involving in the increase or decrease in drugs' solubility start to be approached from a deep thermodynamic point of view, including the analysis of the preferential solvation of solute by the components of mixtures [5][6][7][26][27][28][29][30]. In terms of the considerations mentioned above, the main goal of this work is to report the equilibrium solubility of ribavirin in {methanol (1) + water (2)}, {n-propanol (1) + water (2)}, {acetonitrile (1) + water (2)}+ and {1,4-dioxane (1) + water (2)} mixtures at different temperatures in order to evaluate the respective thermodynamic quantities of the solution, as well as the preferential solvation of the drug by these organic solvents.…”

Experimental and Computational Approaches for Solubility Measurement of Pyridazinone Derivative in Binary (DMSO + Water) Systems

“…Hence, the solubilities and other physicochemical information about these molecules in aqueous-cosolvent binary systems are important for their complete physicochemical characterization [12,13]. The potential of dimethyl sulfoxide (DMSO) in enhancing the solubility of various weakly soluble drugs such as 6-methyl-2-thiouracil, sinapic acid, naringin and bergenin have been proved in the literature [12,[14][15][16]. The solubility data and other physicochemical properties of PPD have been reported poorly in the literature.…”