• Title/Summary/Keyword: β-Cyclodextrin

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A Green Preparation of Drug Loaded PAc-β-CD Nanoparticles from Supercritical Fluid (초임계 유체를 이용한 약물이 담지된 PAc-β-CD 나노 입자의 친환경적인 제조)

  • Jang, Min Ki;Kim, Yong Hun;Kim, Dong Woo;Lee, Si Yun;Lim, Kwon Taek
    • Clean Technology
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    • v.26 no.1
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    • pp.1-6
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    • 2020
  • Rapid expansion of supercritical solution (RESS) process was used to make molsidomine (MOL) loaded peracetyl-β-cyclodextrin (PAc-β-CD) nanoparticles, which were collected into the air. The effect of the concentration of the drug PAc-β-CD (0.5 and 1 wt%), extraction temperature (45 ~ 60 ℃), nozzle length (5 ~ 20 mm) and internal diameter (ID) (50 ~ 150 μm) of a capillary, and spray distance on the particle size and morphology of the resulting particles were investigated. The interaction of a drug and PAc-β-CD was confirmed by 1H-NMR spectroscopy while the particle size was measured by means of a scanning electron microscope. It was found that increasing the temperature from 45 ℃ to 60 ℃ and decreasing the nozzle diameter from 150 μm to 50 μm had an increasing effect on the average particle size, while increasing the spray distance led to a decrease in the average particle size at a constant pressure of 34.5 MPa and temperature of 45 ℃. With 0.5 wt% of PAc-β-CD, the capillary nozzle of short length (5 mm) and small ID (50 μm) gave the smallest size (165 nm). The obtained nanoparticles showed increased dispersity and solubility in oil. The oil suspension of the inclusion complex showed increased sustainability, which can increase the in-vitro controlled release time of the drug.

Optimization of β-Cyclodextrin Recycling Process for Cholesterol Removal in Cream

  • Kwak, H.S.;Suh, H.M.;Ahn, J.;Kwon, H.J.
    • Asian-Australasian Journal of Animal Sciences
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    • v.14 no.4
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    • pp.548-552
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    • 2001
  • This study was designed to find optimum conditions of four different factors (ratio of solvent to cholesterol-$\beta$-cyclodextrin complex, mixing speed, mixing temperature, and mixing time) for cholesterol dissociation in cream. Using the ratio of 6 to 1 (solvent to the complex) showed the highest cholesterol dissociation rate (82.50%) when mixed at 100 rpm at $50^{\circ}C$ for 1 h. Mixing speed did not significantly affect the cholesterol dissociation. Also, mixing time appeared to be insignificant. The optimum mixing temperature was $50^{\circ}C$ and mixing at $40^{\circ}C$ resulted in a significantly lower rate, compared with that at $50^{\circ}C$. In a subsequent experiment, using recycled $\beta$-cyclodextrin only showed 75.07% of cholesterol removal in cream, while the mixture of recycled to unused $\beta$-CD with the ratio of 6 to 4 increased cholesterol removal to 95.59%, which is highly close to that of 100% unused $\beta$-CD.

Preparation and Characterization of Resveratrol Nanoemulsions Stabilized by Self-assembly and Complex Coacervation Consisting of Sodium Alginate, Chitosan, and β-Cyclodextrin

  • Choi, Ae-Jin;Jo, Younghee;Cho, Yong-Jin;Kim, Tae-Eun;Kim, Chong-Tai
    • Food Engineering Progress
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    • v.21 no.3
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    • pp.215-224
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    • 2017
  • Resveratrol was incorporated into various combinations of single- and double-layer nanoemulsions, prepared by self-assembly emulsification and complex coacervation with chitosan, alginate, and ${\beta}$-cyclodextrin, respectively. Resveratrol nanoemulsions were composed of medium-chain trigacylglycerols (MCTs), $Tween^{(R)}$ 80, water, chitosan, alginate, and ${\beta}$-cyclodextrin. The corresponding mixtures were formulated for the purpose of being used as a nutraceutical delivery system. Resveratrol nanoemulsions were obtained with particle sizes of 10-800 nm, with the size variation dependent on the emulsification parameters including the ratio of aqueous phase and surfactant ratio. Resveratrol nanoemulsions were characterized by evaluating particle size, zeta-potential value, stability, and release rate. There were no significant changes in particle size and zeta-potential value of resveratrol nanoemulsions during storage for 28 days at $25^{\circ}C$. The stability of resveratrol in the double-layer nanoemulsions complexed with chitosan or ${\beta}$-cyclodextrin was higher, compared with the single-layer nanoemulsions.

Preparation and Evaluation of Inclusion Complex of Lansoprazole with 2-HP-β-Cyclodextrin and Meglumine (2-HP-β-시클로덱스트린과 메글루민을 이용한 란소프라졸의 포접화합물 제조 및 평가)

  • Lee, Jung-Woo;Kim, Jung-Su;Chang, Hye-Jin;Lee, Gye-Won;Jee, Ung-Kil
    • Journal of Pharmaceutical Investigation
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    • v.34 no.4
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    • pp.269-274
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    • 2004
  • To enhance the solubility and stability of lansoprazole (LAN), new proton pump inhibitor, we were prepared various molar ratio of inclusion complex with $2-hydroxypropyl-{\beta}-cyclodextrin$ (HPCD) and organic alkali agent, meglumine (MEG). Inclusion complex formation of LAN with HPCD was investigated by Differential Scanning Calorimetry and X-ray diffractometry. The aqueous solubilities of inclusion complexes, and the stabilities of 1:4 and 1:5 inclusion complexes in aqueous solutions containing different concentrations of MEG were examined. The stability of 1:5 LAN-HPCD inclusion complex containing MEG, which was equaled to amount of LAN, was performed in 0.9% NaCl and 5% dextrose solution. The formation of inclusion complex of LAN with HPCD was $A_L$ type and the molar ratio of complex was 1:1. The stability constant was $41.557\;M^{-1}$. As molar ratio of LAN to HPCD was increased, solubility of inclusion complex was increased. 1:5 LAN-HPCD inclusion complex was more stable than 1:4 LAN-HPCD inclusion complex. And as contained MEG amount in LAN solution was increased, stability of 1:4 and 1:5 LAN-HPCD inclusion complexes was improved. Also stability of 1:5 LAN-HPCD-MEG inclusion complex in 0.9% NaCl solution and 5% dextrose solution was similar to it in water at room temperature, but it was unstable at $40^{\circ}C$.

Inhibitory Effects of β-Cyclodextrin-Helenalin Complexes on H-TERT Gene Expression in the T47D Breast Cancer Cell Line - Results of Real Time Quantitative PCR

  • Ghasemali, Samaneh;Nejati-Koshki, Kazem;Akbarzadeh, Abolfazl;Tafsiri, Elham;Zarghami, Nosratollah;Rahmati-Yamchi, Mohamad;Alizadeh, Effat;Barkhordari, Amin;Tozihi, Majid;Kordi, Shirafkan
    • Asian Pacific Journal of Cancer Prevention
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    • v.14 no.11
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    • pp.6949-6953
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    • 2013
  • Background: Nowadays, the encapsulation of cytotoxic chemotherapeutic agents is attracting interest as a method for drug delivery. We hypothesized that the efficiency of helenalin might be maximized by encapsulation in ${\beta}$-cyclodextrin nanoparticles. Helenalin, with a hydrophobic structure obtained from flowers of Arnica chamissonis and Arnica Montana, has anti-cancer and anti-inflammatory activity but low water solubility and bioavailability. ${\beta}$-Cyclodextrin (${\beta}$-CD) is a cyclic oligosaccharide comprising seven D-glucopyranoside units, linked through 1,4-glycosidic bonds. Materials and Methods: To test our hypothesis, we prepared ${\beta}$-cyclodextrin-helenalin complexes to determine their inhibitory effects on telomerase gene expression by real-time polymerase chain reaction (q-PCR) and cytotoxic effects by colorimetric cell viability (MTT) assay. Results: MTT assay showed that not only ${\beta}$-cyclodextrin has no cytotoxic effect on its own but also it demonstrated that ${\beta}$-cyclodextrin-helenalin complexes inhibited the growth of the T47D breast cancer cell line in a time and dose-dependent manner. Our q-PCR results showed that the expression of telomerase gene was effectively reduced as the concentration of ${\beta}$-cyclodextrin-helenalin complexes increased. Conclusions: ${\beta}$-Cyclodextrin-helenalin complexes exerted cytotoxic effects on T47D cells through down-regulation of telomerase expression and by enhancing Helenalin uptake by cells. Therefore, ${\beta}$-cyclodextrin could be superior carrier for this kind of hydrophobic agent.

Study of a Supercritical Fluid Process for the Preparation of Hydroxypropyl-β-cyclodextrin Inclusion Complexes (Hydroxypropyl-β-cyclodextrin 포접복합체 제조를 위한 초임계유체 공정 연구)

  • Lee, Sang-Yun;Kim, Jeong-Kyu;Kim, Woo-Sik;Ryu, Jong-Hoon;Lim, Gio-Bin
    • Korean Chemical Engineering Research
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    • v.43 no.1
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    • pp.110-117
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    • 2005
  • In this work, solid-state inclusion complex powders of itraconazole and $2-hydroxypropyl-{\beta}-cyclodextrin(HP-{\beta}-CD)$ were produced by a supercritical anti-solvent (SAS) process. In order to evaluate the degree of complexation, the thermal behavior of the microparticulate complexes was investigated using differential scanning calorimetry. The experimental results obtained 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. The particle size of the SAS-produced inclusion complexes was dramatically reduced ($<0.1-0.5{\mu}m$) compared with untreated itraconazole ($30-50{\mu}m$) and $HP-{\beta}-CD$ ($50-100{\mu}m$). The solubility of itraconazole was increased with the increase of pressure at a constant temperature to ca. $758.6{\mu}g/mL$ in an aqueous medium of pH 1.2. The dissolution rate of itraconazole was observed to be significantly improved and about 90% of itraconazole was found to be dissolved within 5-10 min.

Cholesterol Removal from Whole Egg by Crosslinked β-Cyclodextrin

  • Jeong, H.J.;Sun, H.;Chogsom, C.;Kwak, H.S.
    • Asian-Australasian Journal of Animal Sciences
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    • v.27 no.4
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    • pp.537-542
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    • 2014
  • This study was carried out to optimize cholesterol removal in whole egg using crosslinked ${\beta}$-cyclodextrin (${\beta}$-CD) and to recycle the ${\beta}$-CD. Various factors for optimizing conditions were concentration of the ${\beta}$-CD, mixing temperature, mixing time, mixing speed and centrifugal speed. In the result of this study, the optimum conditions of cholesterol removal were 25% crosslinked ${\beta}$-CD, $40^{\circ}C$ mixing temperature, 30 min mixing time, 1,200 rpm mixing speed and $2,810{\times}g$ centrifugal speed. The recycling was repeated five times. The cholesterol removal was 92.76% when treated with the optimum conditions. After determining the optimum conditions, the recyclable yields of the crosslinked ${\beta}$-CD ranged from 86.66% to 87.60% in the recycling and the percentage of cholesterol removal was over 80% until third recycling. However, the cholesterol removal efficiency was decreased when the number of repeated recycling was increased. Based on the result of this study, it was concluded that the crosslinked ${\beta}$-CD was efficient for cholesterol removal in whole egg, and recycling is possible for only limited repeating times due to the interaction of the ${\beta}$-CD and egg protein.

Prediction of Chiral Discrimination by β-Cyclodextrins Using Grid-based Monte Carlo Docking Simulations

  • Choi, Young-Jin;Kim, Dong-Wook;Park, Hyung-Woo;Hwang, Sun-Tae;Jeong, Karp-Joo;Jung, Seun-Ho
    • Bulletin of the Korean Chemical Society
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    • v.26 no.5
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    • pp.769-775
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    • 2005
  • An efficiency of Monte Carlo (MC) docking simulations was examined for the prediction of chiral discrimination by cyclodextrins. Docking simulations were performed with various computational parameters for the chiral discrimination of a series of 17 enantiomers by $\beta$-cyclodextrin ($\beta$-CD) or by 6-amino-6-deoxy-$\beta$-cyclodextrin (am-$\beta$-CD). A total of 30 sets of enantiomeric complexes were tested to find the optimal simulation parameters for accurate predictions. Rigid-body MC docking simulations gave more accurate predictions than flexible docking simulations. The accuracy was also affected by both the simulation temperature and the kind of force field. The prediction rate of chiral preference was improved by as much as 76.7% when rigid-body MC docking simulations were performed at low-temperatures (100 K) with a sugar22 parameter set in the CHARMM force field. Our approach for MC docking simulations suggested that the conformational rigidity of both the host and guest molecule, due to either the low-temperature or rigid-body docking condition, contributed greatly to the prediction of chiral discrimination.

Complex Formation of Adenosine 3',5'-Cyclic Monophosphate with β-Cyclodextrin: Kinetics and Mechanism by Ultrasonic Relaxation

  • Bae, Jong-Rim;Kim, Jeong-Koo;Lee, Chang-Woo
    • 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.

Influence of Feeding β-Cyclodextrin to Laying Hens on the Egg Production and Cholesterol Content of Egg Yolk

  • Park, B.S.;Kang, H.K.;Jang, A.
    • Asian-Australasian Journal of Animal Sciences
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    • v.18 no.6
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    • pp.835-840
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    • 2005
  • The main objective of the present study was to determine the effect of dietary $\beta$-cyclodextrin ($\beta$-CD) on egg laying performance and cholesterol content of egg yolk. Feed intake, egg production and egg weight varied slightly, but not significantly, between hens fed either a control diet or a diet containing one of an increasing series of $\beta$-CD concentrations (2%, 4% or 6%). However, feed intake, egg production and egg weight were all lower in the hens fed on 8% $\beta$-CD (p<0.05). No difference in haugh unit values, egg yolk color and egg shell thickness were found between the different treatments. The cholesterol content of egg yolks (mg/g yolk) was significantly decreased by 0.71, 2.98, 4.00 and 4.24 mg in eggs from hens maintained on 2%, 4%, 6% and 8% $\beta$-CD, respectively (p<0.05). These observations indicate that appropriate supplementation of diets with $\beta$-CD can reduce the cholesterol content of eggyolks, thus raising the prospect of the production of a healthier functional food.