Thermodynamics of molecular complexation of glycyl–glycyl–glycine with cryptand [2.2.2] in water–dimethylsulfoxide solvent at 298.15 K

Усачева, Т. Р.; Thi, L. Pham; Терехова, И. В.; Kumeev, R. S.; Шарнин, В. А.

doi:10.1007/s10973-016-5383-0

Cited by 6 publications

(3 citation statements)

References 35 publications

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“…The large majority of ITC measurements is conducted in aqueous solutions to study protein-ligand, DNA-drug and/or protein-protein interactions [10] whereas most of the ITC investigations in organic solvents or non-aqueous/aqueous mixtures focus on the solvation or dissolution thermodynamic study of various small molecules [20][21][22][23], drugs [24], single amino acids [25][26][27], small peptides [28], metal ions [29], etc. It is worth noting also some complexation studies for copper ions with β-alanine in ethanol [30], 15-crown-5 ether with Na + in water-ethanol [31], 18-crown-6 with triglycine in water-acetone and water-dimethyl sulfoxide [32], β-cyclodextrin with benzoic acid in water-ethanol [32], fluorescein isothiocyanate with polymers in water-methanol [33], and the association analysis of urea-based supramolecular polymers in different solvents [34].…”

Section: Introductionmentioning

confidence: 99%

Isothermal Calorimetry: Molecular Interactions between Small Molecules in Organic Solvents

Gutiérrez-Climente¹,

Prost²,

Cordin³

et al. 2022

Applications of Calorimetry

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Isothermal titration calorimetry (ITC) is widely used to study protein-ligand, DNA-drug and/or protein-protein interactions but its application for small molecule complexation remains limited namely when the titration is performed in organic solvents. Compared to other dedicated spectroscopic techniques like nuclear magnetic resonance, infrared spectrometry or fluorimetry, which require a series of experiments to extract site-specific stoichiometry and affinity information, ITC provides in a single experiment a complete thermodynamic picture of the overall interaction mechanism. This chapter presents examples that support the high potential of ITC to probe interactions between small molecules in methanol, acetonitrile and methanol/water mixture on a Nano ITC Low Volume device (TA Instruments), with an emphasis on both simple (1:1) and more complex (1:1 and 1:2) interaction mechanisms.

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Section: Introductionmentioning

confidence: 99%

Isothermal Calorimetry: Molecular Interactions between Small Molecules in Organic Solvents

Gutiérrez-Climente¹,

Prost²,

Cordin³

et al. 2022

Applications of Calorimetry

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“…The use of results for binary mixtures of non-aqueous solvents allows to move away from water and its unique properties, thereby showing which solvation contributions determine the changes in the stability of the coordination compound and the energy of the reaction during the transition from one organic solvent to another [ 6 , 7 ]. The analysis of molecular complexation reactions of crown ethers and cryptands with amino acids and peptides shows that the solvation contributions of the host and guest molecules play a different role on the change of the coordination compound and the energy of the reactions [ 8 , 9 ]. To predict the shift of equilibrium in the reactions of biologically active molecules, it is necessary to extend the knowledge of solvent influence on these processes.…”

Section: Introductionmentioning

confidence: 99%

Complexation of Cyclodextrins with Benzoic Acid in Water-Organic Solvents: A Solvation-Thermodynamic Approach

et al. 2021

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The aim of this research is to obtain new data about the complexation between β-cyclodextrin (β-CD) and benzoic acid (BA) as a model reaction of the complex formation of hydrophobic molecules with cyclodextrins (CDs) in various media. This research may help developing cyclodextrin-based pharmaceutical formulations through the choice of the appropriate solvent mixture that may be employed in the industrial application aiming to control the reactions/processes in liquid phase. In this paper, NMR results for the molecular complex formation between BA and β-CD ([BA⊂β-CD]) in D2O-DMSO-d6 and in D2O-EtOH have shown that the stability of the complex in the H2O-DMSO-d6 varies within the experimental error, while decreases in H2O-EtOH. Changes in the Gibbs energy of BA resolvation in water and water–dimethylsulfoxide mixtures have been obtained and have been used in the analysis of the reagent solvation contributions into the Gibbs energy changes of the [BA⊂β-CD] molecular complex formation. Quantum chemical calculations of the interaction energy between β-CD and BA as well as the structure of the [BA⊂β-CD] complex and the energy of β-CD and BA interaction in vacuum and in the medium of water, methanol and dimethylsulfoxide solvents are carried out. The stability of [BA⊂β-CD] complex in H2O-EtOH and H2O-DMSO solvents, obtained by different methods, are compared. The thermodynamic parameters of the [BA⊂β-CD] molecular complexation as well as the reagent solvation contributions in H2O-EtOH and H2O-DMSO mixtures were analyzed by the solvation-thermodynamic approach.

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“…Crown ethers are very well-known and interesting compounds widely used in biology, medicine and chemistry. Because of their structure, they can form complexes with cations [1,2] and small organic molecules [3][4][5][6]. Crown ethers are among the most popular catalysts used in the organic synthesis technique called phase-transfer catalysis [7][8][9][10] and in the nucleophilic substitution [11].…”

Section: Introductionmentioning

confidence: 99%

Effect of properties of the N,N-dimethylformamide + methanol and N,N-dimethylformamide + water mixtures on the solution enthalpy of cyclic ethers in these mixtures at 298.15 K

Jóźwiak

Piekarski

Bińkowska

et al. 2016

J Therm Anal Calorim

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The enthalpies of solution of cyclic ethers [1,4dioxane, 12-crown-4 (12C4), 15-crown-5 (15C5) and 18-crown-6 (18C6)] in N,N-dimethylformamide ? methanol (DMF ? MeOH) mixtures have been measured at 298.15 K. On the basis of the obtained data, the effect of the acid-base and structure-energetic properties of the DMF ? MeOH mixtures on the enthalpy of solution of cyclic ethers in these mixtures has been analyzed. The results have been compared with analogous data concerning the cyclic ethers in N,N-dimethylformamide ? water (DMF ? W) mixtures.

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Thermodynamics of molecular complexation of glycyl–glycyl–glycine with cryptand [2.2.2] in water–dimethylsulfoxide solvent at 298.15 K

Cited by 6 publications

References 35 publications

Isothermal Calorimetry: Molecular Interactions between Small Molecules in Organic Solvents

Isothermal Calorimetry: Molecular Interactions between Small Molecules in Organic Solvents

Complexation of Cyclodextrins with Benzoic Acid in Water-Organic Solvents: A Solvation-Thermodynamic Approach

Effect of properties of the N,N-dimethylformamide + methanol and N,N-dimethylformamide + water mixtures on the solution enthalpy of cyclic ethers in these mixtures at 298.15 K

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