Interactions of theophylline with cyclodextrins in water

Терехова, И. В.; Волкова, Т. В.; Perlovich, German L.

doi:10.1016/j.mencom.2007.06.022

Cited by 7 publications

(5 citation statements)

References 18 publications

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“…A detailed inspection of Table S20 shows that the association of both cyclodextrins with caffeine is characterized by stability constants whose values are close to literature at 298.15 K [85,86,87,88,89,90,91] for studies performed in aqueous solution. Still, for caffeine in the presence of HP- β -CD, the results are comparable even to those under different pH conditions.…”

Section: Resultssupporting

confidence: 66%

“…There is no unanimity in the literature concerning the interaction between theophylline and the cyclodextrin molecules of our study, β -CD and HP- β -CD. In the various available studies [85,90,91,100,101], all authors agree that there is association between theophylline molecules and β -CD molecules, but the value of the equilibrium constant describing this association and the ratio of molecules that are associated are discordant. Ammar et al [101] propose the formation of a complex whose stoichiometry is of the 2:1 type, while the vast majority of authors assume that the association occurs by a 1:1 mechanism.…”

Section: Resultsmentioning

confidence: 99%

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Drug Delivery Systems: Study of Inclusion Complex Formation between Methylxanthines and Cyclodextrins and Their Thermodynamic and Transport Properties

2019

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This paper presents an analysis of the molecular mechanisms involved in the formation of inclusion complexes together with some structural interpretation of drug–carrier molecule interactions in aqueous multicomponent systems comprising methylxanthines and cyclodextrins. The determination of apparent partial molar volumes ( φ V ) from experimental density measurements, both for binary and ternary aqueous solutions of cyclodextrins and methylxanthines, was performed at low concentration range to be consistent with their therapeutic uses in the drug-releasing field. The estimation of the equilibrium constant for inclusion complexes of 1:1 stoichiometry was done through the mathematical modelling of this apparent molar property. The examination of the volume changes offered information about the driving forces for the insertion of the xanthine into the cyclodextrin molecule. The analysis on the volumes of transfer, Δ φ V , c , and the viscosity B-coefficients of transfer, ΔB, for the xanthine from water to the different aqueous solutions of cyclodextrin allowed evaluating the possible interactions between aqueous solutes and/or solute–solvent interactions occurring in the solution. Mutual diffusion coefficients for binary, and ternary mixtures composed by xanthine, cyclodextrin, and water were measured with the Taylor dispersion technique. The behavior diffusion of these multicomponent systems and the coupled flows occurring in the solution were analyzed in order to understand the probable interactions between cyclodextrin–xanthine by estimating their association constants and leading to clearer insight of these systems structure. The measurements were performed at the standard (298.15 ± 0.01) K and physiological (310.15 ± 0.01) K temperatures.

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Section: Resultssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Drug Delivery Systems: Study of Inclusion Complex Formation between Methylxanthines and Cyclodextrins and Their Thermodynamic and Transport Properties

2019

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“…Enthalpies of solution were measured by means of isothermal calorimeter. A detailed description of the calorimeter was presented in our previous work. , The temperature stability was better than 2 × 10 −3 K. The accuracy of weight measurements corresponded to ±10 −6 g. The calorimeter was calibrated using KCl (analytical grade >99.5%, from Merck) in water in a wide concentration interval with a number of measurements of more than 10. The obtained standard value of solution enthalpy was 17225 ± 50 J·mol −1 .…”

Section: Methodsmentioning

confidence: 99%

Thermodynamic and Structural Aspects of Some Fenamate Molecular Crystals

Surov

Терехова

Bauer‐Brandl

et al. 2009

Crystal Growth & Design

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Crystal lattice characteristics from the literature for different polymorphic forms of some nonsteroidal anti-inflammatory drugs (diclofenac, niflumic, flufenamic, tolfenamic, mefenamic acid) and structural relative compounds (N-phenylanthranilic acid and diphenylamine) were summarized and compared. Molecular conformational states in the crystal lattices and hydrogen bond networks were described and analyzed. Temperature dependencies of vapor pressure of the molecular crystals were measured and sublimation thermodynamic parameters calculated. Thermodynamic characteristics of fusion and vaporization processes were derived. Relationships between the sublimation thermodynamic functions and the torsion angles between the benzene motives of the compounds and the polymorphic forms were revealed. Dependence between the sublimation enthalpies and the melting points was observed. Correlation of the fusion entropies with the free volume per molecule in the crystal lattices was found. The absolute values of the crystal lattices energies of the polymorphic forms I and II of mefenamic acid and forms I and III of flufenamic acid were evaluated on basis of the sublimation and solution calorimetric experiments.

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“…Cyclodextrines (CD) are widely applied as non toxic encapsulated materials for a variety of guest molecules in order to improve their physico-chemical properties, such as aqueous solubility, physical chemical stability, and bioavailability of drug. [24][25][26][27][28][29] Due to the fact that the investigated succinimides are slightly soluble in water, their inclusion complexes are prepared in order to enhance their water solubility. Among the host molecules, β-cyclodextrins (β-cyclodextrin (βCD) and (2-hydroxypropyl)-β-cyclodextrin (HPβCD)), built up from seven glucopyranose units, are chosen since they are suitable for complexing molecules bearing phenyl groups such as investigated succinimides.…”

Section: Introductionmentioning

confidence: 99%

Voltammetric Investigation of Inclusion Complexes of the Selected Succinimides with β-Cyclodextrin and (2-Hydroxypropyl)-β-Cyclodextrin

Lović

Ivić²,

Božić³

et al. 2019

ACSi

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The inclusion complexes of the selected, potentially biologically active, succinimides with β-cyclodextrin (βCD) and (2-hydroxypropyl)-β-cyclodextrin (HPβCD) were prepared. The formation of the inclusion complexes of the investigated monophenyl and diphenyl succinimide derivatives was confirmed using attenuated total reflection (ATR) study. Their electrochemical behavior was examined by cyclic voltammetry (CV) and square wave voltammetry (SWV) in 0.05 M NaHCO 3 on a gold electrode. The stability constants for compound 1 were determined by cyclic voltammetry and calculated as K βCD = 350.87 M-1 and K HPβCD = 250.67 M-1. The SWV measurements reveal well defined peak at potential E p = ~ 60 mV and the higher currents at E p for both inclusion complex of the succinimides compared to the free compounds. The impact of chlorine atom in the phenyl moiety of succinimide derivatives on the activity in electrooxidation reaction is presented. Among the studied succinimides, according to SWV measurements, the most active is the monophenyl succinimide derivative (compound 1) in complex with βCD. The difference of peak current of compound 1 + βCD compared to compound 1 + HPβCD and free compound is 6.3 and 35.2 µA cm-2 , respectively.

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Interactions of theophylline with cyclodextrins in water

Cited by 7 publications

References 18 publications

Drug Delivery Systems: Study of Inclusion Complex Formation between Methylxanthines and Cyclodextrins and Their Thermodynamic and Transport Properties

Drug Delivery Systems: Study of Inclusion Complex Formation between Methylxanthines and Cyclodextrins and Their Thermodynamic and Transport Properties

Thermodynamic and Structural Aspects of Some Fenamate Molecular Crystals

Voltammetric Investigation of Inclusion Complexes of the Selected Succinimides with β-Cyclodextrin and (2-Hydroxypropyl)-β-Cyclodextrin

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