• Bulletin of the Korean Chemical Society
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• v.16 no.4
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• pp.305-309
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• 1995

The enantiomeric separation of several amino acid derivatives by reversed-phase liquid chromatography using two (R)-and (S)-naphthylethylcarbamate-β-cyclodextrin(NEC-β-CD) bonded stationary phases was studied to illustrate the chiral recognition model of the enantiomeric separation. The retention and enantioselectivity of the chiral separations with (R)-and (S)-NEC-β-CD bonded phases were compared with similar separations with the native β-CD stationary phases. Especially, the enantioselectivity and elution orders between the derivatized amino acid enantiomers are carefully examined. These results can be illustrated by the chiral recognition models involving inclusion complexation, π-π interaction, and/or hydrophobic interaction. Inclusion complexation and hydrophobic interaction of the naphthyl group of the NEC moiety seem to be major chiral recognition components in the enantiomeric separation of 2,4-dinitrophenyl amino acids and dabsyl amino acids on (R)-and (S)-NEC-β-CD columns. For dansyl amino acids, only the inclusion complexation is the dominant factor. Three different chiral recognition models containing π-π interaction, inclusion complexation and hydrogen bonding were proposed for the separation of the 3,5-dinitrobenzoyl amino acid enantiomers, depending on the size and shape of amino acids.

• Journal of Microbiology and Biotechnology
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• v.11 no.3
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• pp.463-468
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• 2001

Cyclosophoraoses are a class of unbranced cyclic-(1longrightarrow2)-${\beta}$-D-glucans found in the Rhizobium species. Their unique cyclic structures and high solubility make them potent for inclusion complexation as a host for an insoluble guest molecule. A family of neutral cyclosophoraoses (DP 17-27) isolated from Rhizobium meliloti 2011 was used as a host for inclusion complexation with an insoluble guest drug, indomethacin. A high performance liquid chromatographic analysis indicated that the inclusion complexation of cyclosophoraoses greatly ehanced the solubility of indomethacin compared with ${\beta}$-cyclodextrin. The estimated value of the association constant of the complex in water for $\beta$-cyclodextrin and cyclosophoraoses was $523M^{-1} and 17,570M^{-1}$, respectively. NMR spectroscopy showed that the inclusion complex was characterized by the interaction of the indole ring moiety of indomethacin with the cavity of cyclosophoraoses.

• Journal of Pharmaceutical Investigation
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• v.25 no.4
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• pp.283-289
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• 1995

The aim of this study is to increase the solubility and dissolution rate of clonixin by inclusion complex formation. Inclusion complexes of clonixin, a non-steroidal antiinflammatory drug, with ${\beta]-cyclodextrin$ were $2-hydrolrypropyl-{\beta]-cyclodextrin$ were prepared by freeze drying method. Inclusion complex formation of clonixin with cyclodextrins was determined by UV, IR and DSC. The apparent stability constants were calculated from the phase solubility diagrams. Dissolution rate and solubility of clonixin in water markedly increased by the complex formation.

• Korean Journal of Food Science and Technology
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• v.35 no.2
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• pp.266-271
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• 2003

Insoluble polyphenol antioxidants, quercetin and catechin, were stabilized through the complexation with cyclodextrin to increase heat and pH stabilities. Comparison of inclusion complex formabilities of quercetin and catechin with ${\alpha}-,\;{\beta}-$, and ${\gamma}-CDs$ revealed ${\beta}-CD$ to be the most suitable result. Optimal molar mixing ratio of ${\beta}-CD$ and quercetin or catechin for inclusion complex formation was found to be 1 : 1. Inclusion complexation was confirmed using differential scanning calorimetry. Solubility of ${\beta}-CD-antioxidant$ inclusion complexes increased compared with native antioxidants, Stability against temperature and pH of ${\beta}-CD-antioxidant$ inclusion complex analyzed revealed antioxidant activities of ${\beta}-CD-quercetin$ and catechin inclusion complexes have higher stabilization compare to raw quercetin and catechin. Peroxide value of linoleic acid dissolved in water decreased substantionally after using ${\beta}-CD-quercetin$ inclusion complex. ${\beta}-CD-antioxidant$ inclusion complex can be used effectively as a fresh-food preservative.

• Bulletin of the Korean Chemical Society
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• v.26 no.4
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• pp.675-678
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• 2005

• Journal of Pharmaceutical Investigation
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• v.23 no.3
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• pp.155-163
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• 1993

Inclusion complexation of 1,7,21,27-tetraaza[7.1.7.1]paracyclophane (CPM 55) with 2,7-dihydroxynaphthalene (2,7-DHN) or 1,3-dihydroxynaphthalene (1,3-DHN) in pD 1.17 $DCl-D_2O$ solution was investigated by $^1H$ nuclear magnetic resonance spectroscopy (NMR) using 4,4'-dimethylaminodiphenylmethane (ACM 11) as an acyclic analog of CPM 55. In CPM 55-naphthalene derivative complex, alkyl protons located in the cavity of CPM 55 were shown to be subjected to anisotropic shielding and protons of naphthalene moiety shifted remarkably to upfield. However, in ACM 11-naphthalene derivative systems, chemical shifts for protons of both DHN compounds were not significant. The remarkable chemical shift changes suggested that the naphthalene moiety of 2,7-DHN or 1,3-DHN was included in the hydrophobic cavity of CPM 55 in aqueous solution. From the continuous variation plots of induced chemical shifts of 2,7-DHN, it was found that 2,7-DHN was included in the cavity of CPM 55 at 1:1 molar stoichiometry. Both computer simulation of a inclusion complex and strong upfield chemical shift changes of 2,7-DHN protons supported the conformation of pseudoaxial inclusion as the presumed geometry of the host-guest complex.

• YAKHAK HOEJI
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• v.37 no.4
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• pp.331-340
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• 1993

Inclusion complex of omeprazole(OMZ) with hydroxypropyl-$\beta$-cyclodextrin(HP-$\beta$-CD) was prepared by freeze-drying method. The complexation was confirmed by means of UV, CD, IR, DSC, XRD and $^{1}$H-NMR spectra. The benzimidazole moiety of OMZ might be found to be included into the cavity of HP-$\beta$-CD and the inclusion complex appeared to be $A_{L}$ type. The stoichiometric ratio of OMZ : HP-$\beta$-CD was found to be 1:1, and the stability constants of the inclusion complex by solubility and UV method were about 34 and 45 M$^{-1}$, respectively. The dissolution of OMZ was significantly enhanced from powder and. yablet of OMZ-HP-$\beta$-CD complex when compared to those of OMZ alone, and oil-to-water partition coefficient of OMZ-HP-$\beta$-CD complex was significantly higher than that of OMZ alone. Therefore, it was expected that the bioavailability of OMZ could be improved markedly by inclusion complexation of OMZ with HP-$\beta$-CD.

• Journal of Pharmaceutical Investigation
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• v.16 no.2
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• pp.55-67
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• 1986

Inclusion complexation of tiaprofenic acid (TPA) with cyclodextrins $({\alpha}-,\;{\beta}-,\;{\gamma}-CyDs)$ in aqueous solution and in solid phase was investigated by solubility method, measurement of partition coefficient, ultra-violet, circular dichroism, infrared spectroscopies, powder X-ray diffractometry and differential scanning calorimetry. Investigations were made to prepare inclusion complexes of TPA with ${\beta}-CyD$ in solid powdered form by coprecipitation, freeze-drying, spray-drying and co-pulverization methods. The coprecipitation, freeze-drying and spray-drying methods were successful in obtaining inclusion complexes. The results showed that the latter two methods might be originally superior to the former in obtaining powdered inclusion completes. Especially, it was shown by powder X-ray diffractometry that spray-dried ${\beta}-CyD$ alone, TPA-spray-dried ${\beta}-CyD$ physical mixture, and spray-dried $TPA-{\beta}-CyD$ complex were amorphous. The dissolution behaviours of $TPA-{\beta}-CyD$ systems prepared by above four methods were compared with those of TPA alone and $TPA-{\beta}-CyD$ physical mixture, and the rates of dissolution of TPA in pH 1.2 buffer were greatly enhanced by inclusion complexation and copulverization.

• YAKHAK HOEJI
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• v.30 no.2
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• pp.87-95
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• 1986

Inclusion complexation of $\alpha$-cyclodextrin($\alpha$-CD), $\beta$-cyclodextrin($\beta$-CD) and tri-O-methyl-$\beta$-cyclodextrin(tri-O-methyl-$\beta$-CD) with chlorpamide(CPA) in aqueous solution and in the solid state were studied by the solubility method, spectroscopy (UV, IR), differential scanning calorimetry (DSC) and powder X-ray diffractometry, and all their molar ratios were found to be 1:1. The solid complexes of CPA with three kinds of cyclodextrins were prepared by a freezedrying method, and their dissolution behaviors were examined. As a result, the release of CPA from the inclusion complexes was significantly improved. The intrinsic dissolution rate of CPA in cyclodextrin inclusion complexes was about 51 times ($\alpha$-CD inclusion complex) and 12 tmies ($\beta$-CD inclusion complex) larger than that of intact CPA.

• The Journal of the Acoustical Society of Korea
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• v.31 no.2
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• pp.100-106
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• 2012

The aim of this work was to reveal the effect of butanoic acid in its dissociated form and undissociated form as a guest molecule on the kinetic parameters in an inclusion reaction with ${\beta}$-cyclodextrin (${\beta}$-CD). Ultrasonic absorption measurements in the frequency range from 0.2 to 45 MHz were carried out for ${\beta}$-CD solutions with butanoic acid at $25^{\circ}C$ by ultrasonic relaxation method. The rate and the equilibrium constants were obtained from the guest concentration dependence of the relaxation frequency, and the standard volume change of the complexation reaction were obtained from the maximum absorption per wavelength. A single relaxational absorption was observed, and the cause of the relaxation was attributed to a perturbation of the chemical equilibrium associated with a complexation reaction between ${\beta}$-CD and butanoic acid. These results were compared with those in solutions containing both ${\beta}$-CD and different guest molecules. It was found that the hydrophobicity of guest molecules played an important role in the formation of the inclusion complex and also that the charge on the carboxylic group had a considerable effect on the kinetic characteristics of the complexation reaction.