Solubility Behavior and Data Modeling of <scp>l</scp>-Proline in Different Neat and Binary Solvent Systems

Qiu, Jingxuan; Huang, Haishuang; He, Hui; Liu, Haoyou; Hu, Shen; Han, Jiaming; Yi, Dengjing; An, Mengyao; Wang, Peng

doi:10.1021/acs.jced.9b00802

Cited by 47 publications

(51 citation statements)

References 25 publications

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“…All chemicals used in this experiment were maintained in suitable storage conditions and without further treatment. The solubility data of NAM in 16 pure solvents were determined by the static gravimetric method, which has been described , and verified in detail in our previous works. − It can be summarized as the following three steps: (1) solid–liquid phase equilibrium, (2) solid–liquid phase separation, and (3) analysis of the supernatant. Also, the detailed experimental operation for the method can be seen in the Supporting Information.…”

Section: Methodsmentioning

confidence: 90%

Solubility Behavior and Polymorphism of N-Acetyl-dl-methionine in 16 Individual Solvents from 283.15 to 323.15 K

Huang

Qiu

et al. 2021

J. Chem. Eng. Data

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The mole fraction solubility data of N-acetyl-dl-methionine in 16 pure solvents at T = 283.15–323.15 K were measured using the static gravimetric method under a pressure of 98.8 kPa. The polymorphism of N-acetyl-dl-methionine was studied by X-ray powder diffraction analysis, and the results show that there may exist two polymorphs in the studied solid–liquid equilibrium systems. The solubility increased with increasing temperature, and the largest solubility value was obtained in methanol, followed by ethanol > n-propanol > isopropanol > n-butanol > sec-butanol > isobutanol > n-pentanol > acetone > 2-butanone > water > methyl acetate > ethyl acetate > dichloromethane (except for 1,4-dioxane and acetonitrile, which intersect with other solvents). The above solubility behavior is affected by the mutual constraints of polarity, hydrogen bonding, cohesive energy density, viscosity, and molecular structure. In addition, the KAT-LSER model was applied to analyze solute–solvent and solvent–solvent intermolecular interactions. To mathematically represent the measured solubility data, the modified Apelblat model and Yaws model were employed. The average relative deviation (ARD), root-mean-square deviation (RMSD), Akaike information criterion (AIC), and Akaike values of each model were calculated to evaluate the fitting outcomes.

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Section: Methodsmentioning

confidence: 90%

Solubility Behavior and Polymorphism of N-Acetyl-dl-methionine in 16 Individual Solvents from 283.15 to 323.15 K

Huang

Qiu

et al. 2021

J. Chem. Eng. Data

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“…In contrast to trehalose, proline does not induce a glass transition [37,38] and its solubility in water is enormous (it may reach over 15 mol.kg -1 [46,47]). Nevertheless, physical chemistry shows that proline in high concentration also extensively hydrogen bonds with water and together they form a viscoelastic liquid [48][49][50].…”

Section: Proline-rich Viscoelastic Liquid Forms At the Boundary Between Extracellular Ice And Dehydrated Tissuesmentioning

confidence: 99%

“…In contrast to trehalose, proline does not induce a glass transition (Liu et al, 2020;Rasmussen et al, 1997) and its solubility in water is enormous (it may reach over 15 mol.kg -1 (Held et al, 2014;Qiu et al, 2019)). Nevertheless, physical chemistry shows that proline in high concentration also extensively hydrogen bonds with water and together they form a viscoelastic liquid (de Molina et al, 2017;McLain et al, 2007;Troitzsch et al, 2008).…”

Section: Proline-rich Viscoelastic Liquid Forms At the Boundary Between Extracellular Ice And Dehydrated Tissuesmentioning

confidence: 99%

A mixture of innate cryoprotectants is key for freeze tolerance and cryopreservation of a drosophilid fly larva

Kučera

Moos

Štětina

et al. 2021

Preprint

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BackgroundOrganisms evolved biochemical strategies to cope with environmental stressors. For instance, insects that naturally tolerate internal freezing produce complex mixtures of multiple cryoprotectants (CPs). Better knowledge on composition of these mixtures, and on mechanisms of how the individual CPs interact, could inspire development of laboratory CP formulations optimized for cryopreservation of cells and other biological material.ResultsHere we identify and quantify (using high resolution mass spectrometry) a range of putative CPs in larval tissues of a subarctic fly, Chymomyza costata, that survives long-term cryopreservation in liquid nitrogen. The CPs (proline, trehalose, glutamine, asparagine, glycine betaine, glycerophosphoethanolamine, glycerophosphocholine, and sarcosine) accumulate in hemolymph in a ratio of 313:108:55:26:6:4:3:0.5 mmol.L-1. Using calorimetry, we show that the artificial mixtures, mimicking the concentrations of major CPs’ in hemolymph of freeze-tolerant larvae, suppress the melting point of water and significantly reduce the ice fraction. We demonstrate in a bioassay that mixtures of CPs administered through the diet act synergistically rather than additively to enable cryopreservation of otherwise freeze-sensitive larvae. Using MALDI-MSI, we show that during slow extracellular freezing of whole larvae trehalose becomes concentrated in partially dehydrated hemolymph and stimulates transition to the amorphous glass phase. In contrast, proline moves to the boundary between extracellular ice and dehydrated hemolymph and tissues where it likely forms a layer of dense viscoelastic liquid.ConclusionOur results suggest that different components of innate cryoprotective mixtures of freeze-tolerant insect act in synergy during extracellular freezing. We propose that transitions to amorphous glass (stimulated by trehalose) and viscoelastic liquids (having proline as major component) may protect macromolecules and cells from thermomechanical shocks associated with freezing and transfer into and out of liquid nitrogen.

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“…The voltage and current of the tube were set as 40 kV and 150 mA, respectively, and the tested range was from 5 to 60°(2θ degree).The details for preparing the samples is the same as that in our previous works. 17,18 3. SOLUBILITY AND MODEL CALCULATION 3.1.…”

Section: Introductionmentioning

confidence: 99%

Solid–Liquid Equilibrium of l-Thioproline in Nine Neat Solvents and Water + Acetonitrile Binary Solvent System from 283.15 to 323.15 K: Solubility Determination and Data Modeling

Qiu

Wang

et al. 2021

J. Chem. Eng. Data

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The data on the solubility of L-thioproline in a mole fraction scale in nine individual solvents (water, methanol, ethanol, isopropanol, acetone, acetonitrile, dichloromethane, ethyl acetate, and 1,4-dioxane) and one binary solvent mixture of water + acetonitrile was measured by a static gravimetric method from 283.15 to 333.15 K. Whether or not a neat or binary solvent system is used, the solubility is nonlinearly positively correlated with the experimental temperatures. At a given temperature, the solubility presents an order of water > acetone ≈ 1,4-dioxane > dichloromethane ≈ ethanol ≈ ethyl acetate > methanol > isopropanol > acetonitrile, which is a result of the multiple influences of many factors related to intermolecular interactions. Four thermodynamic models, including the modified Apelblat, Yaws, Jouyban−Acree, and Apelblat−Jouyban−Acree models were employed for correlating the solubility data, and the results show a satisfactory fitting effect for each model.

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Solubility Behavior and Data Modeling of l-Proline in Different Neat and Binary Solvent Systems

Cited by 47 publications

References 25 publications

Solubility Behavior and Polymorphism of N-Acetyl-dl-methionine in 16 Individual Solvents from 283.15 to 323.15 K

Solubility Behavior and Polymorphism of N-Acetyl-dl-methionine in 16 Individual Solvents from 283.15 to 323.15 K

A mixture of innate cryoprotectants is key for freeze tolerance and cryopreservation of a drosophilid fly larva

Solid–Liquid Equilibrium of l-Thioproline in Nine Neat Solvents and Water + Acetonitrile Binary Solvent System from 283.15 to 323.15 K: Solubility Determination and Data Modeling

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