• Journal of the Korean Chemical Society
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• v.51 no.6
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• pp.526-535
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• 2007

Ru(II)-terpyridine complexes (8, 9, 11) linked with adamantyl or β-cyclodextrin moieties were synthesized and characterized based on their 1H and 13C NMR spectra as well as MS spectra. Ru(II)-terpyridine complexes (8, 11) linked with adamantyl moiety were readily dissolved in aqueous solution via encapsulation by β-cyclodextrin when they were mixed with an equimolar amount of β-cyclodextrin. In the similar way, the adamantane guest of the Ru(II)-terpyridine complexes (8, 11) were encapsulated by β-cyclodextrin moiety of the ruthenium complex 9 to afford supramolecular assemblies in aqueous environment. Formation of assemblies was corroborated by 1H NMR spectroscopy.

• Food Science and Preservation
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• v.20 no.5
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• pp.659-667
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• 2013

This study was performed to determine the effects of the blanching condition (immersion ratio 1:15 (w/v) for 3 min at $95^{\circ}C$, and solution containing 1% sodium chloride) and selected forming agents (dextrin DE=10, dextrin DE=20, ${\beta}$-cyclodextrin; each forming agents added 5%) on the phytochemical compounds and quality characteristics of Ligularia fischeri leaves. The moisture was not affected by the forming agent. The color of a, b and chroma values were low in the blanching treatment groups and were significantly lowest with ${\beta}$-cyclodextrin (CD). The polyphenol and flavonoid contents in the blanching treatment groups were higher than those in the non-blanching-treatment group. The ascorbic acid content was higher in the non-blanching-treatment group and was significantly highest in the group treated with dextrin (DE=10) whereas the blanching treatment groups showed lower dehydroascorbic acid content than the non-blanching-treatment group. The water absorption was higher in the non-blanching-treatment group and was significantly highest in the group treated with CD. The water solubility in the blanching treatment groups treated with dextrin (DE=20) and CD was higher than that in the blanching treatment group treated with DE=10. The total chlorophyll and chlorophyll a and b contents were high in the blanching treatment group treated with CD, and for the total carotenoid contents, the same tendency as that seen with the chlorophyll content was observed. With regard to the particle diameter, those in the blanching treatment groups were lower than that in the non-blanching-treatment group and was significantly lowest in the blanching treatment groups treated with DE=20 and CD. The result of SEM observation showed that the spray-dried powders in blanching treatment groups treated with the DE=20 and CD forming agents had uniform particle distribution.

• KSBB Journal
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• v.19 no.4
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• pp.321-326
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• 2004

Microparticles of an inclusion complex between itraconazole and 2-hydroxypropyl-${\beta}$-cyclodextrin (HP-${\beta}$-CD) were prepared using an environmentally-benign supercritical anti-solvent (SAS) process. In order to evaluate the degree of complexation, the thermal behavior of solid micro particulate complexes was investigated using differential scanning calorimetry. The experimental results obatined for the solubility and dissolution rate of the microparticulate inclusion complexes in a buffer solution of pH 1.2 showed that the complexation of itraconazole with HP-${\beta}$-CD results in a significant increase in the solubility and dissolution rate of itraconazole. For the microparticulate itraconazole/Hp-${\beta}$-CD inclusion complexes prepared by the SAS process, about 80% of itraconazole was found to dissolve in the buffer solution. Our experimental results confirmed that the SAS process is a promising method for the preparation of microparticles of water-insoluble drug/cyclodextrin inclusion complexes.

• Korean Journal of Food Science and Technology
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• v.29 no.2
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• pp.302-308
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• 1997

${\beta}-Cyclodextrin\;({\beta}-CD)$ polymers were prepared using epichlorohydrin as a cross linking agent. The polymers were separated into ${\beta}-CD$ soluble polymer $({\beta}-CD\;SP)$ and ${\beta}-CD$ insoluble polymer $({\beta}-CD\;ISP)$ on a 10,000 molecular weight cut-off membrane (YM 10). Optimum separation conditions in the YM 10 were: transmembrane pressure 51.7 kPa, separation temperature $35^{\circ}C$, and volume concentration ratio 10. The flux was $0.025\;mL/cm^{2}/min$ under the optimum conditions. Gel permeation chromatography indicated that ${\beta}-CD\;SP\;and\;{\beta}-CD\;ISP$ had a degree of polymerization of $2{\sim}8$ and over 10, respectively. The formation of an inclusion complex with hydrophobic compounds such as 4-dimethylaminoazobenzene, methyl red, and naringin was compared among ${\beta}-CD,\;{\beta}-CD\;SP\;and\;{\beta}-CD\;ISP$. The molar absorptivity for the two chromatic compounds was increased and the absorption peak was shifted in the presence of ${\beta}-CD$ polymers. Naringin, the principal flavonoid bitter tasting component of citrus fruit, had a low water solubility. The solubility of naringin was increased through the formation of an inclusion complex with ${\beta}-CD$ polymers. There was no significant difference in the formation of an inclusion complex between ${\beta}-CD\;SP\;and\;{\beta}-CD\;ISP$. Reduction of the bitter components from citrus products was shown to be possible when employing ${\beta}-CD\;SP$, while the usage of ${\beta}-CD$ monomer has been limited due to the low water solubility.

• Korean Journal of Pharmacognosy
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• v.46 no.2
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• pp.133-139
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• 2015

Two coumarinolignans, cleomiscosins C (1) and D (2) were isolated from the heartwood of Acer mono, together with four compounds, 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (3), 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-apiofuranosyl-(1$\rightarrow$6)-${\beta}$-D-glucopyranoside (4), scopoletin (5), and (E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (6). Of them, cleomiscosins C (1) and D (2) were applied to preparing inclusion complex molecules with ${\beta}$-cyclodextrin (${\beta}$-CD) to improve the very poor solubility in cell media. The CD complexes of 1 and 2 exhibited an enhancement of water solubility which is feasible to measure their cytotoxicity using a spectrophotometer in a cell-based assay. Anti-proliferative activity of these complex molecules was successfully estimated on HCT116 human colon cancer cells, and cleomiscosin D (2) showed anti-proliferative effects at the concentration of 1.95~31.2 ${{\mu}g}$/mL in a dose-dependent manner.

• Bulletin of the Korean Chemical Society
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• v.31 no.2
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• pp.442-446
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• 2010

Adenosine 3',5'-cyclic monophosphate (cAMP) is a second messenger responsible for a multitude of cellular responses. In this study, we utilized $\beta$-cyclodextrin ($\beta$-CD) as an artificial receptor with a hydrophobic cavity to elucidate the inclusion kinetics of cAMP in a hydrophobic environment using the ultrasonic relaxation method. The results revealed that the interaction of cAMP with $\beta$-CD followed a single relaxation curve as a result of host-guest interactions. The inclusion of cAMP into the $\beta$-CD cavity was found to be a diffusion-controlled reaction. The dissociation of cAMP from the $\beta$-CD cavity was slower than that of adenosine 5'-monophosphate (AMP). The syn and anti glycosyl conformations of adenine nucleotides are considered to play an important role in formation of the inclusion complex. Taken together, our findings indicate that hydrophobic interactions are involved in the inclusion complex formation of cAMP with $\beta$-CD and provide insight into the interactions of cAMP with cAMP-binding proteins.

• 한국생물공학회:학술대회논문집
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• 2001.11a
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• pp.656-659
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• 2001

Cyclodextrin glucanotransferase (CGTase) (EC 2.4.1.19) use starch to produce cyclic maltooligosaccharides (cyclodextrins, CDs) which are of interest in various applications. To obtain a novel CGTase having high CD-forming activity, ${\beta}-cyclodextrin$ glucanotransferase $({\beta}-CGTase)$ from Bacillus firmus var. alkalophilus was modified through site-directed mutagenesis and constructed five mutants, H59T, H59Q, Y96M, 9O-PPI-93, and ${\Delta}(148-154)D$, respectively. Y96M and ${\Delta}(148-154)D$ showed much higher level of conversion yields of starch into CDs from 28.6% to about 39% compared to wild-type ${\beta}-CGTase$, respectively, but 90-PPI-93 maintained similar convesion yields of starch to CDs. And their ${\beta}-CD$ ratios to total CDs were not changed and maintained, and convesion yields to linear maltooligosaccharides of all mutants were not changed significantly. These results indicates that five mutations of ${\beta}-CGTase$ from Bacillus firmus var. alkalophilus appears to be important roles for increase of overall CD production rather than change of its product specificity, especially.

• YAKHAK HOEJI
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• v.38 no.4
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• pp.372-378
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• 1994

Choleretic effect and absorption of ursodeoxycholic acid (UDCA) in rats were studied using UDCA alone and it's ${\beta}-cyclodextrin$ $({\beta}-CyD)$ inclusin complex (UDCA-IC). In spite of increase in solubility and dissolution rate, absorption of UDCA-IC was decreased compared with UDCA alone. Choleretic effect of UDCA-IC was also decreased. It looks that UDCA forms stronger inclusion complex with ${\beta}-CyD$ than any other drug or organic biological material. From this study, it was suggested that UDCA might be used as a new potential competing agent when inclusion complexes of drugs with ${\beta}-CyD$ were administered for the improvement of poor bioavailability.

• YAKHAK HOEJI
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• v.38 no.3
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• pp.300-310
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• 1994

Physicochemical properties for the inclusion complex of chenodeoxycholic acid(CDCA) and it's $7{\beta}-hydroxy$ epimer ursodeoxycholic acid(UDCA) with ${\beta}-cyclodextrin({\beta}-CyD)$ were studied. The formation of the complex in the solid state were confimed by polarized microscopy and differential scanning calorimetry(DSC). Proton nuclear magnetic resonance$(^1H-NMR)$spectroscopy showed that CDCA and UDCA form an inclusion complex with ${\beta}-CyD$ in aqueous solution. The 1 : 1 stoichiometry of the complex was dextermined by the continuous variation method. From DSC and $^1H-NMR$ studies, there were not any differences between CDCA and UDCA. Complex of CDCA and UDCA showed increase in solubility and dissolution compared with CDCA and UDCA alone, respectively. Solubility pattern of UDCA complex was pH independent but, CDCA complex was like that of CDCA. Dissolution rate increased markedly in case of UDCA complex compared with CDCA complex, especially in acidic pH value.

• Bulletin of the Korean Chemical Society
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• v.24 no.11
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• pp.1627-1631
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• 2003

Molecular modeling was performed to comprehend the chiral recognition of ${\alpha}$-methoxy-${\alpha}$-trifluoromethylphenylacetic acid (MTPA) enantiomers by cyclomaltoheptaose (${\beta}$-cyclodextrin,${\beta}$-CD) and 6-amino-6-deoxy-cyclomaltoheptaose (am-${\beta}$-CD). Monte Carlo (MC) docking coupled to constant temperature molecular dynamics (MD) simulations was applied to the investigation for the ${\alpha}$-methoxy-${\alpha}$-trifluoromethylphenylacetic acid complexation with two different CDs in terms of the relative distribution of the interaction energies. The calculated results are finely correlated with the experimental observations in chiral recognition thermodynamics. Am-${\beta}$-CD as a host showed the superior enantio-discrimination ability to the native ${\beta}$-CD where the amino group of am-${\beta}$-CD was critically involved in enhancing the ability of chiral discrimination via the Coulombic interaction with MTPA.