NMR Studies of Cyclodextrins and Cyclodextrin Complexes

Hj, Schneider; Hacket, Frank; Rüdiger,; Ikeda, Hiroshi

doi:10.1021/cr970019t

Cited by 1,418 publications

(950 citation statements)

References 292 publications

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“…NMR is an analytical technique extensively used for structural elucidation of organic compounds and also to investigate intra-/inter-molecular interactions (37). For example, the proton chemical shifts between a free guest molecule and its inclusion complex with cyclodextrin can be observed and compared to investigate the possible interaction between the guest molecule and cyclodextrin.…”

Section: Nuclear Magnetic Resonance Studymentioning

confidence: 99%

Masking the Bitter Taste of Injectable Lidocaine HCl Formulation for Dental Procedures

et al. 2014

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Abstract. Several attempts have been made to mask the bitter taste of oral formulations, but none have been made for injectable formulations. This study aims to mask the bitter taste of dental lidocaine HCl (LID) injection using hydroxypropyl-β-cyclodextrin (HP-β-CD) and sodium saccharin. Inclusion complexes of LID and HP-β-CD were prepared by the solution method in 1:1 and 1:2 M ratios. Inclusion complexes in solution were studied using phase solubility in phosphate buffer solutions (pH 8, 9, and 10). Freeze-dried inclusion complexes were characterized using differential scanning calorimetry (DSC), Xray, Fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR), scanning electron microscopy (SEM), and in vitro release. Injectable formulations were prepared using inclusion complexes and characterized for stability and for taste using an Alpha MOS ASTREE electronic tongue (ETongue). The association constants of HP-β-CD with lidocaine-free base and its ionized form were found to be 26.23± 0.00025 and 0.8694±0.00045 M −1 , respectively. Characterization studies confirmed the formation of stable inclusion complexes of LID and HP-β-CD. Injectable formulations were found to be stable for up to 6 months at 4°C, 25°C, and 40°C. The taste evaluation study indicated that HP-β-CD (1:1 and 1:2 M ratios) significantly improved the bitter taste of LID injectable formulation. In conclusion, inclusion complex in the 1:1 M ratio with 0.09% sodium saccharin was considered to be optimum in masking the bitter taste of LID.

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Section: Nuclear Magnetic Resonance Studymentioning

confidence: 99%

Masking the Bitter Taste of Injectable Lidocaine HCl Formulation for Dental Procedures

et al. 2014

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“…The fact this group shows a strong stretching absorption band in the region of 1870-1540 cm -1 is due to a constant position, high intensity and freedom from interfering bands, which make it useful to recognize in the IR spectra [25,33]. The range between 900-600 cm -1 presents more intense and informative bands in the spectra of aromatic compounds [15,25] (Fig.…”

Section: -Indomethacinmentioning

confidence: 99%

The influence of the preparation methods on the inclusion of model drugs in a β-cyclodextrin cavity

Salústio

Feio

Figueirinhas³

et al. 2009

European Journal of Pharmaceutics and Biopharmaceutics

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The work aims to prove the complexation of two models drugs (ibuprofen, IB and indomethacin, IN) by beta-cyclodextrin (βCD), the effect of the water in such process, and the comparison of their complexation yields. Two methods were considered: kneading of a binary mixture of the drug:βCD and inclusion of either IB or IN in aqueous solutions of βCD. In the latter method the water was removed by air stream, spray-drying and freeze-drying. To prove the formation of complexes in final products optical microscopy, UV spectroscopy, IR spectroscopy, DSC, X-Ray and NMR were considered. Each powder was added to an acidic solution (pH = 2) to quantify the concentration of the drug inside βCD cavity. Others media (pH = 5 and 7) were used to prove the existence of drug not complexed in each powder as the drugs solubility increases with the pH. It was observed that complexation occurred in all powders, and that the fraction of drug inside the βCD did not depend neither on the method of complexation nor on the processes of drying considered.

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“…Many factors contribute to the stability of these inclusion complexes, but because the formation of most complexes is exothermic, lowering the solution temperature favors complex formation and stability (69,70). For the ␣HL pore, the stability of CD within the ␣HL pore was potentiated when the cavity of the CD was occupied by small organic guest molecules (19).…”

Section: Cd-induced Block Is Not Specific For the Urea Or The Sucrosementioning

confidence: 99%

Reversible Pore Block of Connexin Channels by Cyclodextrins

Locke

Koreen

Liu

et al. 2004

Journal of Biological Chemistry

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Cyclodextrins (CDs), a series of hollow cyclic glucosaccharides, can reversibly block molecular permeation through channels formed by connexin-32 and/or connexin-26 reconstituted into liposomes. The character of the block changes as a function of the size of the CD relative to the connexin pore diameter, suggesting that the block occurs via entry of the CD into the pore lumen and occlusion of the permeability pathway. The block occurs only when the CD is applied to the side of the pore that is normally cytoplasmic and not from the side that is normally extracellular. The block is potentiated when organic analytes are sequestered in the hydrophobic interior of the CDs. CDs may be useful as molecular tools with which to explore the structure of the connexin pore and to alter molecular movement through connexin channels.

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NMR Studies of Cyclodextrins and Cyclodextrin Complexes

Cited by 1,418 publications

References 292 publications

Masking the Bitter Taste of Injectable Lidocaine HCl Formulation for Dental Procedures

Masking the Bitter Taste of Injectable Lidocaine HCl Formulation for Dental Procedures

The influence of the preparation methods on the inclusion of model drugs in a β-cyclodextrin cavity

Reversible Pore Block of Connexin Channels by Cyclodextrins

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