Solubility modelling and preferential solvation of paclobutrazol in co-solvent mixtures of (ethanol, n -propanol and 1,4-dioxane) + water

Chen, Jiao; Chen, Gaoquan; Cong, Yang; Du, Cunbin; Zhao, Hongkun

doi:10.1016/j.jct.2017.05.004

Cited by 68 publications

(76 citation statements)

References 32 publications

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“…Finally, it is noteworthy that in our previous studies [63][64][65], the solute is preferentially solvated by co-solvent in co-solventrich mixtures. However, ribavirin (II) is preferentially solvated by water in this region.…”

Section: Preferential Solvation Of Ribavirinmentioning

confidence: 72%

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

Cong

et al. 2017

The Journal of Chemical Thermodynamics

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a b s t r a c tThe equilibrium solubility of ribavirin in solvent mixtures of {methanol (1) + water (2)}, {n-propanol (1) + water (2)}, {acetonitrile (1) + water (2)} and {1,4-dioxane (1) + water (2)} was determined experimentally by using isothermal dissolution equilibrium method within the temperature range from (278.15 to 318.15) K under atmospheric pressure (101.1 kPa). At the same temperature and mass fraction of methanol (n-propanol, acetonitrile or 1,4-dioxane), the mole fraction solubility of ribavirin is greater in (methanol + water) than in the other three solvent mixtures. The preferential solvation parameters were derived from their thermodynamic solution properties by means of the inverse Kirkwood-Buff integrals. The preferential solvation parameters for methanol, n-propanol, acetonitrile or 1,4-dioxane (dx 1,3 ) were negative in the four solvent mixtures with a very wide compositions, which indicated that ribavirin was preferentially solvated by water. Temperature had little effect on the preferential solvation magnitudes. The higher solvation by water could be explained in terms of the higher acidic behaviour of water interacting with the Lewis basic groups of the ribavirin. Besides, the solubility of the drugs was mathematically represented by using the Jouyban-Acree model, van't Hoff-Jouyban-Acree model and Apelblat-Jouyban-Acree model obtaining average relative deviations lower than 1.57% for correlative studies. It is noteworthy that the solubility data presented in this work contribute to expansion of the physicochemical information about the solubility of drugs in binary solvent mixtures and also allows the thermodynamic analysis of the respective dissolution and specific solvation process.

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Section: Preferential Solvation Of Ribavirinmentioning

confidence: 72%

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

Cong

et al. 2017

The Journal of Chemical Thermodynamics

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“…The Jouyban–Acree model could be expressed as eq . ,− ,,, It is able to provide precise description for the dependence of solute solubility on both solvent composition and temperature for binary and ternary mixtures. where w 1 and w 2 are, respectively, the weight composition of cosolvent (1) and water (2) in 3,5-dinitrosalicylic acid-free solutions studied; x 3 represents the mole fraction solubility of 3,5-dinitrosalicylic acid in binary aqueous systems containing one of DMF, ethanol, NMP, and isopropanol at absolute temperature T and mass fraction, w 1 , of the cosolvents (DMF, ethanol, NMP, and isopropanol); x 1,T and x 2,T are solubility magnitudes of 3,5-dinitrosalicylic acid in neat cosolvent (1) and water (2) at T /K, respectively; and J i signifies equation constants.…”

Section: Computation Methodologiesmentioning

confidence: 99%

“…Water is generally used as a preferred solvent in industrial processes to reduce the production cost. With the aim of improvement of the solubility magnitude for many poorly soluble compounds, numerous chemical/pharmaceutical fields prefer to utilize cosolvent + water mixture, which is normally employed as a recrystalline and reaction medium. ,,, The comprehensive knowledge of suitable solvents and their dissolution facility of crystalline solid compounds can provide valuable help in screening the optimum quantity of solvents in numerous applications. , Also, the solubility of solid substance in cosolvent mixtures allows us to study in-depth thermodynamic aspects to distinguish the intra- and intermolecular interactions in dissolution process, in conjunction with the preferential solvation analysis of solid drugs by the specific solvent speices. − Consequently, determination of solubility of solid drugs in different aqueous blends is crucial for many pharmaceutical producers.…”

Section: Introductionmentioning

confidence: 99%

Solubility Measurement, Preferential Solvation, and Solvent Effect of 3,5-Dinitrosalicylic Acid in Several Binary Aqueous Blends

et al. 2021

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This research dealt with the equilibrium solubility, preferential solvation, and intra- and intermolecular interactions for 3,5-dinitrosalicylic acid dissolved in aqueous blends of N-methyl-2-pyrrolidinone (NMP)/ethanol/isopropanol/N,N-dimethylformamide (DMF) along with computational methodologies. All solubility experiments were performed using a shake-flask equilibration method under a pressure of 101.2 kPa from 278.15 to 323.15 K. For each aqueous blend, the minimum solubility value of 3,5-dinitrosalicylic acid was found in water at 278.15 K, and the maximum one was found in neat organic solvent at 323.15 K. The generated solubility was acceptably described by mixture response surface, van’t Hoff–Jouyban–Acree, modified Wilson and Jouyban–Acree model. The relative average deviations were all no larger than 5.57%. The analysis of linear solvation energy relationships demonstrated that the solvent descriptors of dipolarity-polarizability and solubility parameter were principally responsible for the 3,5-dinitrosalicylic acid solubility. Besides, the solvation of 3,5-dinitrosalicylic acid was studied quantitatively by inverse Kirkwood–Buff integrals. The positive values of preferential solvation parameter for 3,5-dinitrosalicylic acid in middle and cosolvent-rich mixtures strongly suggest that 3,5-dinitrosalicylic acid is preferentially solvated by NMP/ethanol/isopropanol/DMF. It could be conjectured that in these composition regions, 3,5-dinitrosalicylic acid served as Lewis acid in its interactions with surrounding NMP/ethanol/isopropanol/DMF molecules.

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“…This concept was greatly influenced by Ben-Naim who applied the Kirkwood-Buff integrals to obtain relationships between local compositions and experimentally measureable properties. 72 Several solvent mixtures have been modeled for their local composition around a drug 73,74 and an excellent review by Marcus outlines alternative theoretical frameworks of preferential solvation. 75 Recent work complemented preferential solvation calculations with a visualization of the solute's local environment by means of a MD simulation.…”

Section: Cosolventsmentioning

confidence: 99%

Synergistic Computational Modeling Approaches as Team Players in the Game of Solubility Predictions

Kuentz

Bergström

2021

Journal of Pharmaceutical Sciences

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Several approaches to predict and model drug solubility have been used in the drug discovery and development processes during the last decades. Each of these approaches have their own benefits and place, and are typically used as standalone approaches rather than in concert. The synergistic effects of these are often overlooked, partly due to the need of computational experts to perform the modeling and simulations as well as analyzing the data obtained. Here we provide our views on how these different approaches can be used to retrieve more information on drug solubility, ranging from multivariate data analysis over thermodynamic cycle modeling to molecular dynamics simulations. We are discussing aqueous solubility as well as solubility in more complex mixed solvents and media with colloidal structures present. We conclude that the field of computational pharmaceutics is in its early days but with a bright future ahead. However, education of computational formulators with broad knowledge of modeling and simulation approaches is imperative if computational pharmaceutics is to reach its full potential.

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Solubility modelling and preferential solvation of paclobutrazol in co-solvent mixtures of (ethanol, n -propanol and 1,4-dioxane) + water

Cited by 68 publications

References 32 publications

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

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

Solubility Measurement, Preferential Solvation, and Solvent Effect of 3,5-Dinitrosalicylic Acid in Several Binary Aqueous Blends

Synergistic Computational Modeling Approaches as Team Players in the Game of Solubility Predictions

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