• 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.

• YAKHAK HOEJI
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• v.39 no.2
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• pp.175-184
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• 1995

The interaction of omeprazole(OMP) with $\gamma$-cyclodextrin($\gamma$-CyD) was investigated by solubility study and the complexation was confirmed by means of UV/VIS spectrophotometer, circular dichroism, differential scanning calorimeter, and $^{1}$H nuclear magnetic resonance spectra. The stability, dissolution rate, and partition coefficient of the complex were measured. The results present that the benzimidazole moiety and a part of pyridine ring containing sulfur atom of OMP might be included into the cavity of $\gamma$-CyD and the formation type of inclusion complex appeared to be B$_{s}$. The stoichiometric ratio of OMP to $\gamma$-CyD in the complex was found to be 1:1 and the stability constant of the complex found to be 97.1 M$^{-1}$. And the dissolution rate of OMP was markedly increased by inclusion complex formation with $\gamma$-CyD, and so it was above 90% in 5 min. from solid complex. Oil to water partition coefficient of OMP-$\gamma$-CyD complex was 60, which is significantly higher than that of OMP itself, 36.4. The degradation rate constant of OMP were greater than OMP-$\gamma$-CyD complex in aqueous solutions of various pHs, and the half lives of OMP and OMP-$\gamma$-CyD at pH 9 were 279.2 and 509.9 days, respectively, showing that the complex was more stable than OMP, therefore it was thought that OMP was stabilized by inclusion formation with $\gamma$-CyD.

• KSBB Journal
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• v.27 no.2
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• pp.109-113
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• 2012

This research was to examine the effects of various cyclodextrins on the solubility and stability of prodigiosin in seawater. Among them, ${\beta}$-cyclodextrin was found to have the best efficiency and formation of the inclusion complex was saturated when prodigiosin and ${\beta}$-cyclodextrin were mixed in a ratio of 1:8 and shaken at $25^{\circ}C$ and pH 8.0 for 6 h. The maximum algicidal activity against Chattonella antiqua using the inclusion complex stored at $4^{\circ}C$ for 5 weeks of culture was obtained, $52.28{\pm}3.41%$, which was about 5.0 fold higher than that of control. Our results suggest that inclusion complexes of prodigiosin and ${\beta}$-cyclodextrin could serve as effective algicidal agents.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1997.04a
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• pp.116-116
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• 1997

Complex formation of practically insoluble dexamethasone dipropionate (DDP) with ${\beta}$-cyclodextrin (${\beta}$-CD), dimethyl-${\beta}$-cyclodextrin (DMCD), trimethyl-${\beta}$-cyclodextrin (TMCD), 2-hydroxypropyl-${\beta}$-cyclodextrin (HPCD) and sulfobutyl ether ${\beta}$-cyclodextrin (SBCD) in water was investigated by solubility method at various temperatures. Water solubility of DDP was found to be 1.78 $\mu\textrm{g}$/$m\ell$ at 37$^{\circ}C$. Propylene glycol (PG)-water cosolvent increased the solubility of DDP, but the solubilization was not sufficient (8.93 $\mu\textrm{g}$/$m\ell$ in 20% PG). The addition of CD markedly increased the solubility of DDP in water, and A$\sub$L/ type phase solubility diagrams were obtained with ${\beta}$-CD, TMCD, HPCD and SBCD, where the apparent stability constants of the soluble complexes at 25$^{\circ}C$ were determined to be 1388, 216, 1054, and 1992 M$\^$-1/, respectively. However, DMCD remarkably increased the solubility of DDP, and showed an A$\sub$P/ type diagram, suggesting that DMCD forms a soluble complex of high order with DDP. The stability constant for the DDP-DMCD complex at 25$^{\circ}C$ was determined to be 19132 M$\^$-1/. The thermodynamic parameters were calculated for the inclusion complex formation in aqueous solution. CD (1${\times}$10$\^$-2/M) remarkably decreased the partition coefficients of DDP between isopropyl myristate/water in the order of TMCD < ${\beta}$-CD < HPCD < SBCD < DMCD, and in squalane/water system in the order of HPCD < TMCD < ${\beta}$-CD < DMCD < DMCD $\leq$ SBCD. This finding represents that, in a o/w type cream, cyclodextrin complexation with DDP may result in high concentration of DDP in aqueous phase. The permeation of DDP through a cellophane membrane was highly suppressed by the addition of CD, and the degree of suppression was different among CDs, indicating that CD may control the skin permeation of DDP. The dissolution rates of solid dispersions with CDs were much faster than those of drugs alone and corresponding physical mixtures. All DDP-CD solid dispersions exceeded the equilibrium solubility. Consequently these results suggest that complex formation of DDP with CDs may provide useful means to markedly enhance the solubility, and CDs are useful in the semi-solid preparations such as creams and gels for topical application.

• Journal of Pharmaceutical Investigation
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• v.26 no.3
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• pp.169-174
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• 1996

Inclusion complexes of diclofenac sodium with ${\beta}-cyclodextrin$ were prepared in aqueous solution, alkaline solution and solid phase. The interaction of diclofenac sodium with ${\beta}-cyclodextrin$ in pH 9.0 alkaline solution was evaluated by the solubility method and the instrumental analysis such as thermal analysis, infrared spectroscopy, X-ray diffractometry. The solubility of diclofenac sodium was increased linearly with the increase in the concentration of ${\beta}-cyclodextrin$up to 0.15 mol and showed that the aqueous solubility rate of diclofenac sodium was significantly increased by complex with ${\beta}-cyclodextrin$. The optimum composition of this complex was one molecule of ${\beta}-cyclodextrin$ included 1.59 molecular weight of diclofenac sodium as a guest molecule. The pharmacokinetic parameters of the diclofenac sodium and the complex with ${\beta}-cyclodextrin$ were studied in rats by oral route. $T_{max}$ between drug alone and inclusion complex showed significant difference to be 120 minute and 20 minute respectively. Both of $C_{max}$ and AUC of inclusion complex was about 40% higher than drug alone. It is estimated from the data in this study that complexation of diclofenac sodium with ${\beta}-cyclodextrin$ increased the absorption rate and improved the bioavalability of the diclofenac sodium by the formation of a water-soluble complexes.

• Korean Journal of Food Science and Technology
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• v.26 no.1
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• pp.6-11
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• 1994

A cyclodextrin glucanotransferase(CGTase)-producing Bacillus sp. I-5 was isolated from soil and the enzyme exhibited the maximum reaction rate at pH 8.0 and $50^{\circ}C$. It was found that CGTase of I-5 produced ${\beta}-$ and ${\gamma}-CD$ mainly but the production ratio of cyclodextrins (CDs) was influenced by the buffer solution. Sodium acetate significantly stimulated the formation of ${\gamma}-CD$, increasing the content by 35%. The production of CDs was influenced by DE value of starch. The results indicated that DE value in the range of $3.5{\sim}6.0$ were most effective for the CD formation. CGTase was immobilized on the reversibly soluble-insoluble carrier, hydroxypropyl mothylcellulose acetate succinate. The immobilized CGTase was soluble at pH 7.5, and precipitated easily at pH 6.0. Enzyme reactor was designed to produce CD continuously. It was composed of three major stages-CD produttion by immobilized CGTase, conversion of the residual dextrin to glucose by amylase and glucoamylase and alcohol fermentation by yeasts to remove the glucose into alcohol. The yield of total CDs was 3.65g from 10g soluble starch.

• Journal of Pharmaceutical Investigation
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• v.15 no.1
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• pp.15-21
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• 1985

The inclusion of ${\alpha}-cyclodextrin$ and ${\beta}-cyclodextrin$ with flurbiprofen in aqueous phase was investigated by UV absorption and circular dichroism spectroscopies. The inclusion complex in solid powder form were made by the freeze-drying and coprecipitation methods in molar ratio 1:1. The inclusion complex formation was confirmed by infrared absorption spectroscopy. The freeze-drying method was successful in obtaining the inclusion compounds compared with the coprecipitation method. The dissolution of solid flurbiprofen inclusion complex was examined in comparison with those of flurbiprofen alone. The inclusion complex obtained by freeze-drying method increased the dissolution rate.

• Journal of Pharmaceutical Investigation
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• v.18 no.4
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• pp.181-186
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• 1988

Inclusion complex of sulfamethoxazole with ${\beta}-cyclodextrin$ was prepared by freeze-drying method in molar ratios of 1:1, 1:1.25, 1:1.5 and 1:1.75, and the complex formation was identified by ultraviolet and infrared spectroscopies, powder X-ray diffractometry and differential scanning calorimetry. Dissolution rate and solid state stability of the complex were investigated in comparison with those of sulfamethoxazole powder and the physical mixture of sulfamethoxazole with ${\beta}-cyclodextrin$. As a result, the dissolution rate and the stability of solid complexes in various relative humidity conditions increased more remarkably than those of sulfamethoxazole powder and physical mixture. But the difference according to molar ratio of the complex was not recognized.

• Applied Chemistry for Engineering
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• v.32 no.5
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• pp.504-508
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• 2021

In this study, the effect of molecular features of guest molecules on the structure, property, and formation of poly(vinyl alcohol) (PVA)/beta-cyclodextrin (bCD) inclusion compound hybrid films was investigated using three types of guest molecules such as hydroquinone (HQ), arbutin (AB), and tranexamic acid (TA). First, the successful formation of inclusion compounds between bCD and the guest molecules, and polymer/inclusion compound hybrid were proved using Raman spectroscopy. The effect of bCD-based inclusion compounds on the structure and property of PVA matrix composites containing inclusion compounds was also studied using X-ray diffraction (XRD) and thermal analyses such as differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). It was notable that the effect of TA to the crystalline structure of the PVA was significantly different from that of using other guest molecules including HQ and AB. It was also supported by a simple molecular simulation result. This article will be a good example for demonstrating the effect of molecular characteristics on the inclusion compound formation in polymer films, which can provide important information for relevant future research.

• Proceedings of the Polymer Society of Korea Conference
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• 2006.10a
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• pp.351-351
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• 2006

The possible interactions between cyclodextrins and biodegradable polyesters were investigated. The hydrophobicity of cyclodextrin could be varied with the methyl substitution of host CD, and the possibility of IC formation and the types of interaction between respective CDs and polyesters were subsequently changed. Further, the effect of cyclodextrins on the morphological change of biodegradable polymer was shown to depend on the degree of IC formation between cyclodextrin and biodegradable polymer as well as on the type of interaction between respective CDs and polyesters. That is, the enhancement and/or the restriction of the crystallization of P(3HB) were observed by the incorporation of various kind of cyclodextrins with different cavity size and hydrophobicity.