High field NMR techniques and molecular modelling study of the inclusion complexes of the nootropic drug tenilsetam (CAS-997) in cyclodextrins

Amato, Maria E.; Djedaïni‐Pilard, Florence; Perly, Bruno; Scarlata, Giuseppe

doi:10.1039/p29920002065

Cited by 35 publications

(19 citation statements)

References 13 publications

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“…See, e.g. reports on the interaction of naproxen,23, 24 tenilsetam,25 suronacrine,26 CI‐844,27 cocaine,28 salbutamol,29 nicardipine,30 doxepin31 and midazolam32 with α‐ or β‐cyclodextrins. These accounts are also classic illustrations of the NMR approach.…”

Section: Introductionmentioning

confidence: 99%

Precision studies in supramolecular chemistry: a ¹H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Fielding¹,

McKellar

Florence

2011

Magnetic Reson in Chemistry

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The association constants for the interactions of 2-hydroxy-4-methoxyacetophenone, 2-hydroxy-5-methoxyacetophenone, 2-hydroxy-6-methoxyacetophenone, 3-hydroxy-4-methoxyacetophenone and 4-hydroxy-3-methoxyacetophenone with β-cyclodextrin in water were measured by (1)H NMR and by isothermal titration calorimetry. Very good agreement was obtained between the different methods. The errors associated with the NMR method for measuring mM binding affinities were estimated to be 10-30%, and by isothermal titration calorimetry, 10-20%. Rotating frame nuclear Overhauser effect spectroscopy studies show that the solution phase host-guest complexes formed by β-cyclodextrin with these hydroxymethoxyacetophenone derivatives are not structurally well defined but that the hydroxymethoxyacetophenone derivatives are mostly associated with the narrow primary hydroxyl rim.

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Section: Introductionmentioning

confidence: 99%

Precision studies in supramolecular chemistry: a ¹H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Fielding¹,

McKellar

Florence

2011

Magnetic Reson in Chemistry

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“…In order to gain some information about intermolecular accompanying complexation, we decided to employ high resolution nuclear magnetic resonance (NMR) spectroscopy. It is generally accepted that NMR is a far more sensitive tool for studying intermolecular interactions and host-guest complexes, [17][18][19][20][21] because the host and guest molecules are simultaneously observed. Application of high resolution NMR can provide not only quantitative information but also a large amount of detailed information useful to determine the disposition of the guest molecule relative to the host.…”

Section: Introductionmentioning

confidence: 99%

Preparation and spectroscopic studies of an inclusion complex of adenine with β-cyclodextrin in solution and in the solid state

Liang

Chao

2002

Analyst

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The interaction between adenine and beta-CD has been investigated in solution and in the solid state by several analytical techniques, primarily by 1H-NMR, 2D ROESY and fluorescence spectra, and secondarily by other important techniques, for example, Fourier transform infrared spectroscopy (FT-IR) and differential scanning calorimetry (DSC). The association constant and 1:1 nature of the complex between adenine and beta-CD in solution were determined by fluorescence spectroscopy. A spatial configuration for the complex in solution is proposed from analysis of the 1H-NMR and 2D ROESY data. The Fourier transform infrared spectroscopy (FT-IR) and differential scanning calorimetry (DSC) data are consistent with the formation of an inclusion complex. In addition, a solid inclusion complex of adenine with beta-CD was synthesized by the coprecipitation method.

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“…Reactions involving cyclodextrins are of importance to the technology of drug delivery systems, separations, and foods. − These reactions also serve as excellent models for understanding the basis of inclusion chemistry and as models of (enzyme + substrate) interactions . The principal factors involved in the binding are believed to be primarily van der Waals forces and hydrophobic effects.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic and Nuclear Magnetic Resonance Study of the Reactions of α- and β-Cyclodextrin with Acids, Aliphatic Amines, and Cyclic Alcohols

Rekharsky¹,

Mayhew²,

Goldberg³

et al. 1997

J. Phys. Chem. B

179

153

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Titration calorimetry was used to determine equilibrium constants and standard molar enthalpy, Gibbs energy, and entropy changes for the reactions of a series of acids, amines, and cyclic alcohols with α- and β-cyclodextrin. The results have been examined in terms of structural features in the ligands such as the number of alkyl groups, the charge number, the presence of a double bond, branching, and the presence of methyl and methoxy groups. The values of thermodynamic quantities, in particular the standard molar Gibbs energy, correlate well with the structural features in the ligands. These structural correlations can be used for the estimation of thermodynamic quantities for related reactions. Enthalpy−entropy compensation is evident when the individual classes of substances studied herein are considered, but does not hold when these various classes of ligands are considered collectively. The NMR results indicate that the mode of accommodation of the acids and amines in the α-cyclodextrin cavity is very similar, but that the 1-methyl groups in 1-methylhexylamine and in 1-methylheptylamine and the N-methyl group in N-methylhexylamine lie outside the α-cyclodextrin cavity. This latter finding is consistent with the calorimetric results. Many of the thermodynamic and NMR results can be qualitatively understood in terms of van der Waals forces and hydrophobic effects.

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High field NMR techniques and molecular modelling study of the inclusion complexes of the nootropic drug tenilsetam (CAS-997) in cyclodextrins

Cited by 35 publications

References 13 publications

Precision studies in supramolecular chemistry: a ¹H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Precision studies in supramolecular chemistry: a ¹H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Preparation and spectroscopic studies of an inclusion complex of adenine with β-cyclodextrin in solution and in the solid state

Thermodynamic and Nuclear Magnetic Resonance Study of the Reactions of α- and β-Cyclodextrin with Acids, Aliphatic Amines, and Cyclic Alcohols

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High field NMR techniques and molecular modelling study of the inclusion complexes of the nootropic drug tenilsetam (CAS-997) in cyclodextrins

Cited by 35 publications

References 13 publications

Precision studies in supramolecular chemistry: a 1H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Precision studies in supramolecular chemistry: a 1H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Preparation and spectroscopic studies of an inclusion complex of adenine with β-cyclodextrin in solution and in the solid state

Thermodynamic and Nuclear Magnetic Resonance Study of the Reactions of α- and β-Cyclodextrin with Acids, Aliphatic Amines, and Cyclic Alcohols

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Precision studies in supramolecular chemistry: a ¹H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes

Precision studies in supramolecular chemistry: a ¹H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes