Enthalpy and entropy changes on molecular inclusion of pentane derivatives into α-cyclodextrin cavities in aqueous solutions

Kimura, Takayoshi; Fujie, Satoshi; Yukiyama, Takashi; Fujisawa, Masao; Kamiyama, Tadashi; Aki, Hatsumi

doi:10.1007/s10847-010-9877-2

Cited by 6 publications

(2 citation statements)

References 14 publications

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“…Extensive research has been undertaken to investigate the thermodynamics of non-pharmaceutical, chemicalcyclodextrin complexes, including pentane derivatives, hexanol, cyclohexanol, butadienenol, adamantine, benzoic acid, aspartame, bile acids and many others [5][6][7] but to date, only very limited research has been focused on probing the thermodynamics of drug-cyclodextrin complexes, despite its importance in formulation process, product stability and ultimately drug dissociation in vivo [8]. In a previous paper, we have studied stability and structures of inclusion complexes between zaleplon (ZAL), a non-benzodiazepine hypnotic drug indicated for short term management of insomnia, and a series of natural and chemically modified CDs in order to select the derivate with the most pronounced complexing and solubilising potential for the drug [9].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic study of inclusion complexes of zaleplon with natural and modified cyclodextrins

Jug

Jablan

Kövér

et al. 2013

J Incl Phenom Macrocycl Chem

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The thermodynamics and stoichiometry of zaleplon (ZAL) complexation with different cyclodextrin derivatives [b-CD, hydroxypropyl-b-cyclodextrin (HP-b-CD), randomly methylated-b-cyclodextrin (RAMEB), sulphobutylether-b-cyclodextrin (SBE-b-CD)] in aqueous solution was studied by spectrofluorimetry and 1 H NMR spectroscopy in order to obtain a more general understanding of the driving forces behind the inclusion phenomena. Job's plot derived from the NMR spectral data and statistical analysis of spectrofluorimetric titration data confirmed the formation of equimolar complexes in all systems tested, excluding the possibility of higher order complex formation. Furthermore, thermodynamic parameters obtained by both techniques gave similar and negative values of DG°for all complexes, indicating spontaneous inclusion of drug into CDs. From a thermodynamic point of view, two types of inclusions were determined. One is enthalpy driven ZAL complexation with b-CD, HP-b-CD and RAMEB, while the other is entropy driven complexation observed in the case of SBE-b-CD. The mechanisms behind each type of inclusion were discussed in detail.

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Section: Introductionmentioning

confidence: 99%

Thermodynamic study of inclusion complexes of zaleplon with natural and modified cyclodextrins

Jug

Jablan

Kövér

et al. 2013

J Incl Phenom Macrocycl Chem

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“…Therefore, it is vital to elucidate the role of asymmetric intermolecular interactions due to the stereospecific structure of a molecule in order to understand the mechanisms of chemical and biochemical reactions. In previous research, thermodynamic functions for the molecular inclusion of simple molecules into αand β-cyclodextrin (CD) cavities in dilute aqueous solutions were systematically determined using microcalorimetry in order to clarify the mechanism of molecular recognition and discrimination [1][2][3][4][5][6][7][8][9][10]. Improvements in the stability and solubility of drugs can be expected from formation of CD-drug inclusion complexes.…”

Section: Introductionmentioning

confidence: 99%

Interaction Energy Analysis for Drug-Cyclodextrin Inclusion Complexes in Aqueous Solutions

Fujisawa¹

2012

J. Appl. Sol. Chem. Model.

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It is vital to elucidate the role of asymmetric intermolecular interactions resulting from the stereospecific structures of molecules in order to understand the mechanisms of chemical and biochemical reactions such as enzymesubstrate reactions, antigen-antibody reactions, etc. In order to reveal the mechanism of the inclusion phenomenon for β-cyclodextrin (CD)-ampicillin complexes and β-CD-ibuprofen complexes, binding free energies were determined using molecular mechanics/Poisson-Boltzmann surface area (MM/PBSA) analysis. To clarify the details of the interaction energies of these complexes, pair interaction energy decomposition analysis (PIEDA) was carried out. The direction of inclusion of drugs into β-CD cavities was clarified on the basis of results obtained using the above-mentioned methods.

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A kinetic and thermodynamic study of the α-cyclodextrin mediated reaction of a range of p-substituted phenyl methyl sulfides with binding and non-binding peroxyacids

Deary

Mousa

Davies

2011

J Incl Phenom Macrocycl Chem

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Enthalpy and entropy changes on molecular inclusion of pentane derivatives into α-cyclodextrin cavities in aqueous solutions

Cited by 6 publications

References 14 publications

Thermodynamic study of inclusion complexes of zaleplon with natural and modified cyclodextrins

Thermodynamic study of inclusion complexes of zaleplon with natural and modified cyclodextrins

Interaction Energy Analysis for Drug-Cyclodextrin Inclusion Complexes in Aqueous Solutions

A kinetic and thermodynamic study of the α-cyclodextrin mediated reaction of a range of p-substituted phenyl methyl sulfides with binding and non-binding peroxyacids

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