Solubility of <scp>d</scp>-Histidine in Aqueous Cosolvent Mixtures of N,N-Dimethylformamide, Ethanol, Dimethyl Sulfoxide, and N-Methyl-2-pyrrolidone: Determination, Preferential Solvation, and Solvent Effect

Li, Wanxin; Farajtabar, Ali; Rong, Xing; Zhu, Yiting; Zhao, Hongkun

doi:10.1021/acs.jced.9b01051

Cited by 8 publications

(8 citation statements)

References 47 publications

(117 reference statements)

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“…It has been reported that imidazole and amino acid Pro can stabilize the interaction of the lysozyme–NAG 3 complex. ,, Here, imidazole, amino acids, acetonitrile, NMP, and DMF were applied to lysozyme solutions with flavonoids for ESI-MS, respectively. Both NMP and DMF are common cosolvents used in the pharmaceutical field and show high solubilization ability. , It was found that addition of imidazole, amino acids, and acetonitrile could not improve the stability of lysozyme–flavonoid complexes (data not shown), and only DMF and NMP were found to be very good at stabilizing the labile lysozyme–flavonoid complexes.…”

Section: Resultsmentioning

confidence: 99%

Stabilization of Labile Lysozyme–Ligand Interactions in Native Electrospray Ionization Mass Spectrometry

Zhao

Xing

et al. 2023

J. Am. Soc. Mass Spectrom.

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Flavonoids are polyphenolic secondary metabolites with extensive biological activities and pharmacological effects. Exploring the interactions of flavonoids with proteins may be helpful for understanding their biological processes. Electrospray ionization mass spectrometry (ESI-MS) is a powerful tool to characterize the noncovalent protein−ligand (PL) complexes. However, some protein−flavonoid complexes are labile during electrospray ionization. Here, the labile lysozyme−flavonoid (rutin, icariin, and naringin) complexes were determined by direct ESI-MS without derivation. It has been found that low amounts of N-methylpyrrolidinone and dimethylformamide can protect labile lysozyme-flavonoid complexes away from dissociation during electrospray ionization process. The intact lysozyme-flavonoid complexes were specifically observed in mass spectra, and the measured binding affinities by ESI-MS were matched with the fluorescence data. The effects of additives on the analysis of lysozymeflavonoid complexes were investigated by ESI-MS, combined with the molecular docking and fluorescence. This strategy was helpful to investigate the labile PL interactions by direct ESI-MS.

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Section: Resultsmentioning

confidence: 99%

Stabilization of Labile Lysozyme–Ligand Interactions in Native Electrospray Ionization Mass Spectrometry

Zhao

Xing

et al. 2023

J. Am. Soc. Mass Spectrom.

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“…The last term indicates the energy term for solvent–solvent interactions, where c i = 1–4 demonstrates the sensitivity of solute solubility to the corresponding solute–solvent and solvent–solvent molecular interactions. The independent coefficient c 0 shows the effect of the crystal lattice properties of the solute on the solubility . It is also called the ideal solubility ( x ideal ) estimated by the solid–liquid phase equilibrium thermodynamics (described by eq ).…”

Section: Model Calculation Sectionmentioning

confidence: 99%

“…The independent coefficient c 0 shows the effect of the crystal lattice properties of the solute on the solubility. 22 It is also called the ideal solubility (x ideal ) estimated by the solid−liquid phase equilibrium thermodynamics (described by eq 10). 23…”

Section: Model Calculation Sectionmentioning

confidence: 99%

Determination and Correlation of the Solubility of d(−)-Salicin in Pure and Binary Solvent Systems

Huang

Qiu

et al. 2020

J. Chem. Eng. Data

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Experimental solubility data of d(−)-salicin in twelve neat solvents (methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-pentanol, acetone, acetonitrile, 1,4-dioxance, ethyl acetate, and water) and four binary solvents (water + ethanol, water + acetone, water + isopropanol, and water + methanol) in the temperature range from 283.15 to 323.15 K under atmosphere pressure were determined using the gravimetric method. When the solvent composition was constant, a positive correlation of d(−)-salicin solubility with experimental temperature was found in all investigated pure and mixed solvent systems. At a given temperature, inflection points were found in the solubility curves for binary solvent systems as the mole fraction of water increased, which may be attributed to the cosolvency phenomenon. For the monosolvents, the solubility of d(−)-salicin may be affected by certain factors, such as polarity, steric effects, dipolarity–polarizability, hydrogen bonds, and so on. The KAT-LSER model was used to perform the multiple linear regression analysis on pure and mixed solvent systems to reveal the solute–solvent and solvent–solvent interactions. Finally, the modified Apelblat model, the Jouyban–Acree model, and the Apelblat–Jouyban–Acree model were utilized to correlate the solubility data.

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“…Furthermore, some aqueous mixtures of NMP have been analyzed in cosolvency studies for increasing the equilibrium solubility of several drugs and drug-like compounds, as was compiled in the published literature. , The specific compounds include terephthalic acid, sebacic acid, , 1,12-decanedioic acid, 1-naphthoic acid, , phenobarbital, − griseofulvine, , phenytoin, ,, ketoprofen, , estrone, , testosterone, , ibuprofen, ,, amiodarone, , carbendazim, , 2-phenoxypropionic acid, , (2 R )-2-[4-(7-chloroquinoxalin-2-yl)oxyphenoxy]propanoic acid (XK-469), , a benzoylphenyl urea derivative, , 2-(2-thiophenyl)-4-azabenzoimidazole (PG-300995), , clonazepam, diazepam, lamotrigine, acetaminophen, amiodarone·HCl, celecoxib, 6-methyl-2-thiouracil, ketoconazole, allopurinol, chloroxine, d -histidine, 5-aminosalicylic acid, bisacodyl, amoxicillin, 5-nitrofurazone, biapenem, phenformin, griseofulvine, and sulfadiazine …”

Section: Introductionmentioning

confidence: 99%

Effect of N-Methyl-pyrrolidone (NMP) on the Equilibrium Solubility of Meloxicam in Aqueous Media: Correlation, Dissolution Thermodynamics, and Preferential Solvation

et al. 2022

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Meloxicam is an analgesic and anti-inflammatory drug widely prescribed in current therapeutics that exhibits very low solubility in water. Thus, this physicochemical property has been studied in N-methyl-pyrrolidone (NMP)−aqueous mixtures at several temperatures to expand the solubility database about pharmaceutical compounds in aqueous−mixed solvents. The flask-shake method and UV−vis spectrophotometry were used for meloxicam solubility determination as a function of temperature and mixture composition. Several cosolvency models, including the Jouyban−Acree model, were challenged for equilibrium solubility correlation and/or prediction. The van't Hoff and Gibbs equations were employed here to calculate the apparent standard thermodynamic quantities for the dissolution and mixing processes of this drug in these aqueous mixtures. Inverse Kirkwood−Buff integrals were employed to calculate the preferential solvation parameters of meloxicam by NMP in all mixtures. Meloxicam equilibrium solubility increased with increasing temperature, and maximal solubilities were observed in neat NMP at all temperatures. The mole fraction solubility of meloxicam increased from 1.137 × 10 −6 in neat water to 3.639 × 10 −3 in neat NMP at 298.15 K. The Jouyban−Acree model correlated the meloxicam solubility in these mixtures very well. Dissolution processes were endothermic and entropy-driven in all cases, except in neat water, where nonenthalpy-nor entropy-driven was observed. Apparent Gibbs energies of dissolution varied from 34.35 kJ•mol −1 in pure water to 7.99 kJ•mol −1 in pure NMP at a mean harmonic temperature of 303.0 K. A nonlinear enthalpy−entropy relationship was observed in the plot of dissolution enthalpy vs dissolution Gibbs energy. Meloxicam is preferentially hydrated in water-rich mixtures but preferentially solvated by NMP in the composition interval of 0.16 < x 1 < 1.00.

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Solubility of d-Histidine in Aqueous Cosolvent Mixtures of N,N-Dimethylformamide, Ethanol, Dimethyl Sulfoxide, and N-Methyl-2-pyrrolidone: Determination, Preferential Solvation, and Solvent Effect

Cited by 8 publications

References 47 publications

Stabilization of Labile Lysozyme–Ligand Interactions in Native Electrospray Ionization Mass Spectrometry

Stabilization of Labile Lysozyme–Ligand Interactions in Native Electrospray Ionization Mass Spectrometry

Determination and Correlation of the Solubility of d(−)-Salicin in Pure and Binary Solvent Systems

Effect of N-Methyl-pyrrolidone (NMP) on the Equilibrium Solubility of Meloxicam in Aqueous Media: Correlation, Dissolution Thermodynamics, and Preferential Solvation

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