Solubility of hesperidin drug in aqueous biodegradable acidic choline chloride-based deep eutectic solvents.

Important efforts have been made over the past years to improve the drug acts, which leads to the discovery of novel drug preparations and delivery systems. The selection of suitable green solvents for novel drug discovery and drug delivery depends on a molecular-level understanding of the interaction between drug molecules and the solvents. Deep eutectic solvents (DESs) are already used in sustainable extraction methods of natural products for their very high solvent power, high chemical and thermal stability, non-toxicity, and non-flammable. The thermodynamic investigation provides deep and complete knowledge of interactions and the choice of appropriate and suitable production compounds in pharmaceutical fields. Particularly, the analysis of drugs+DESs in aqueous media is a central issue in many types of research. This research is aimed to determine hesperidin (HES) solubility in water and DES solvents [choline chloride/citric acid (ChCl/CA), choline chloride/oxalic acid (ChCl/OA), choline chloride/malonic acid (ChCl/MA), and choline chloride/lactic acid (ChCl/LA)] at temperature range (298.15-313.15 K). Furthermore, the measured solubility data of HES in studied aqueous DESs solutions was fitted by models of Van't Hoff-Jouyban-Acree and Modified Apelblat-Jouyban-Acree. Finally, the Hansen solubility parameters as thermodynamic aspect for analyzing the dissolution processes for the four investigated aqueous DESs solutions were estimated.

Deep eutectic solvents for antiepileptic drug phenytoin solubilization: thermodynamic study.

Thermodynamic investigations provide information about the solute-solvent interactions in the selection of the proper solvent for different fields of pharmaceutical sciences. Especially, the study of antiepileptic drugs in solutions (ethanol/co-solvent) has been a subject of interest owing to their effect in the systems using interaction with a number of important biological membranes. This work focuses on the measurement of density and speed of sound of the phenytoin (PTH) in ethanol/deep eutectic solvents (choline chloride:ethylene glycol, and choline chloride:glycerol) solutions as the innovative class of green solvents at temperature range (288.15 to 318.15) K. It was determined Hansen solubility parameters for assessment of PTH interactions in the solvent media. Some thermophysical parameters including apparent molar volumes Vϕ, apparent molar isobaric expansion [Formula: see text], and Hepler's constant, apparent molar isentropic compressibility κφ were obtained and calculated using these data. To correlate  the Vϕ and κφ values, the Redlich-Meyer equation was used to calculate the number of quantities containing standard partial molar volume and partial molar isentropic compressibility. Finally, [Formula: see text] values showed a strong interaction between PTH and solvent (ethanol/DES (ChCl:EG)). The thermodynamic analysis of the studied system also plays a crucial role in the pharmaceutical industry.

Cytotoxicity of some choline-based deep eutectic solvents and their effect on solubility of coumarin drug.

The effect of some deep eutectic solvents (DESs) on the coumarin solubility has been investigated using Hansen solubility parameters (HSP). The solubility of coumarin was measured in aqueous systems containing some DESs based on choline chloride (ChCl) as hydrogen bond acceptor (HBA) with urea (U), ethylene glycol (EG), and glycerol (GLY) as hydrogen bond donors (HBD) by widely applied shake-flask method at T = (298.15 to 313.15) K. The results indicate that coumarin solubility enhances with the concentration of DESs and temperature. Also, coumarin was dissolved more than 80 times compared with pure water in the presence of ChCl/EG. Then experimental data were fitted to Wilson, electrolyte Non-Random Tow-Liquid (e-NRTL), and UNIQUAC activity coefficient models. Furthermore, the dissolution thermodynamic properties including enthalpy, Gibbs free energy, and entropy have been calculated based on Gibbs and van't Hoff equations. Due to these results, it is indicated that coumarin dissolution in the studied systems is an endothermic process. Moreover, to investigate the biological properties of DESs, MTT assay have been applied to determinate cytotoxicity of the DESs. In the melanoma skin cell line, cell culture tests revealed that these solvents had very low toxicity and high biocompatibility.

Effect of Tetrabutylammonium Bromide-Based Deep Eutectic Solvents on the Aqueous Solubility of Indomethacin at Various Temperatures: Measurement, Modeling, and Prediction with Three-Dimensional Hansen Solubility Parameters.

Deep eutectic solvents (DESs) have recently been getting a great deal of attention in many fields of science and technology. The objective of this study was to peruse the solubility of indomethacin (IMC) as sparingly soluble drug in some tetrabutylammonium bromide (TBAB)-based DESs (TBAB/ethylene glycol and TBAB/glycerol). The shake flask method has been employed in this study at temperature ranges T = (298.15-313.15) K and atmospheric pressure (pP = 86.6 kPa). The results showed that the solubility of IMC in TBAB/ethylene glycol system was obtained approximately 17,000-fold more than its solubility in water. The solubility data were accurately correlated by the famous local composition activity coefficient models including e-NRTL and UNIQUAC. It was also our aim to evaluate Hansen solubility parameters in IMC solubility prediction. These parameters can help to predict the solvent performance during the manufacturing processes and will be useful in guessing solvent behavior in many other fields of effort. The experimental and the Hansen solubility parameters results are very well matched. In addition, the apparent thermodynamic properties of dissolution and mixing were studied in these solutions based on Van't Hoff and Gibbs equations.