• Title/Summary/Keyword: beta-cyclodextrin

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NMR Spectroscopic Analysis on the Chiral Recognition of Noradrenaline by β-Cyclodextrin ( β-CD) and Carboxymethyl- β-cyclodextrin (CM- β-CD)

  • Lee, Sang-Hoo;Yi, Dong-Heui;Jung, Seung-Ho
    • Bulletin of the Korean Chemical Society
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    • v.25 no.2
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    • pp.216-220
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    • 2004
  • ${\beta}$-CD and CM- ${\beta}$-CD as chiral NMR shift agents were used to resolve the enantiomers of noradrenaline (NA). The stoichiometry of each complex formed between the CDs and the enantiomers of NA was found to be 1 : 1 through the continuous variation plots. The binding constants (K) of the complexes were determined from $^1H$ NMR titration curves. This result indicated that both ${\beta}$-CD and CM- ${\beta}$-CD formed the complexes with the S(+)-NA more preferentially than its R(-)-enantiomer. The K values for the complexes with ${\beta}$-CD ($K_{S(+)}$ = 537 $M^{-1}$ and $K_{R(-)}$ = 516 $M^{-1}$ was larger than those with CM- ${\beta}$-CD ($K_{S(+)}$ = 435 $M^{-1}$ and $K_{R(-)}$ = 313 $M^{-1}$), however, enantioselectivity (${\alpha}$) of S(+)- and R(-)-NA to CM- ${\beta}$-CD ( ${\alpha}$ = 1.38) was larger than that to ${\beta}$-CD ( ${\alpha}$ = 1.04), indicating that CM- ${\beta}$-CD was the better chiral NMR solvating agents for the recognition of the enantiomers of NA. Two dimensional rotating frame nuclear Overhauser enhancement spectroscopy (ROESY) experiments were also performed to explain the binding properties in terms of spatial fitting of the NA molecule into the macrocyclic cavities.

Solubilization by $\beta$-Cyclodextrin: A Fluorescence Quenching Study

  • Panda, M.;Mishra, A.K.
    • Journal of Photoscience
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    • v.9 no.3
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    • pp.75-79
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    • 2002
  • Solubility of carbon tetrachloride ($CCl_4$) in water increases appreciably in presence of $\beta$-cyclodextrin ($\beta$CD). $CCl_4$ is a very good quencher of 1-naphthol (1ROH) fluorescence. By studying the quenching of fluorescence of 1ROH included in $\beta$CD cavity, it was found that there is an increase in the availability of $CCl_4$ around $\beta$CD in the aqueous medium. This could help to rationalize the enhanced solubility of $CCl_4$.

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Supramolecular aminocatalysis via inclusion complex: Amino-doped β-cyclodextrin as an efficient supramolecular catalyst for the synthesis of chromeno pyrimido[1,2-b]indazol in water

  • Shinde, Vijay Vilas;Jeong, Daham;Jung, Seunho
    • Journal of Industrial and Engineering Chemistry
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    • v.68
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    • pp.6-13
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    • 2018
  • Well-modified amino-appended ${\beta}$-cyclodextrin ($AA-{\beta}-CD$) with an amino group at the primary face of the ${\beta}-CD$ was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. $AA-{\beta}-CD$ was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly.

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.

Encapsulation of $\beta$-cyclodextrin including DHA using Curdlan (커들란을 이용만 $\beta$-cyclodextrin에 포접된 DHA의 캡슐화)

  • 이기영;이창문;최창남;김동운;이인영
    • KSBB Journal
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    • v.17 no.1
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    • pp.54-58
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    • 2002
  • Curdlan gel containing various hydrophobic materials was prepared. The homogenized suspension of curdlan and hydrophobic materials was healed at $100^{\circ}C$. The curdlan gel can contain hydrophobic material up to 27%(v/v). When gel was compressed, only water in the gel was removed. When immersed in water, the dried gel absorbed water and became the original wet gel. The syneresis of gel decreased with the concentration of hydrophobic material added. DHA content of dried gel was about 90%. $\beta$-cyclodextrin inclusion complexes containing DHA were prepared with addition of water and ethanol. X-ray diffractograms of complexes showed a specific peak at 7-$8^{\circ}C$ and FT-IR spectrum of complex showed a specific C=O peak at $1745\textrm{cm}^{-1}$. Inclusion complex containing DHA was microcapsulated with curdlan and pullulan.

Effects of Dietary ${\beta}$-Cyclodextrin on Plasma Lipid and Tissue Cholesterol Content in Swine

  • Park, B.S.;Jang, A.
    • Asian-Australasian Journal of Animal Sciences
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    • v.20 no.1
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    • pp.100-105
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    • 2007
  • This study examined the effects of dietary ${\beta}$-cyclodextrin (${\beta}CD$) on the cholesterol of blood and tissues of swine. Thirty six male castrated swine ($Landrace{\times}Yolkshire{\times}Duroc$) weighing 50 kg were randomly assigned to one of four dietary groups until their weight reached 110 kg. The groups were: basal diet without ${\beta}CD$ (control) and basal diets containing 1.5%, 3.0%, or 5.0% ${\beta}CD$. Diets and water were offered ad libitum. No significant difference was found between treatments in terms of feeding performance measured by daily intake, daily weight gain, and feed efficiency. Addition of ${\beta}CD$ to the diets significantly reduced total lipid, triglyceride and total cholesterol levels in swine blood, particularly in the group receiving 5.0% ${\beta}CD$, which showed decreases (p<0.05) of 21.9%, 55.6% and 27.7%, respectively. Cholesterol levels in back fat, loin, belly and ham portions of swine fed ${\beta}CD$ significantly differed (p<0.05) from controls, especially in the 5.0% ${\beta}CD$-fed group, with reductions of 26.0%, 27.5%, 17.9% and 18.3%, respectively. These results suggested that the addition of ${\beta}CD$ to the diet of swine could reduce their body cholesterol by decreasing the migration of cholesterol through the blood.

Entrapment of Milk Nutrients during Cholesterol Removal from Milk by Crosslinked β-Cyclodextrin

  • Ha, H.J.;Jeon, S.S.;Chang, Y.H.;Kwak, H.S.
    • Food Science of Animal Resources
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    • v.29 no.5
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    • pp.566-572
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    • 2009
  • This study was designed to elucidate the quantities of milk nutrients entrapped during cholesterol removal from milk by crosslinked $\beta$-cyclodextrin ($\beta$-CD, 0.4~1.2%, w/v) and to evaluate the amounts of the residual $\beta$-CD in cholesterol-reduced milk treated by crosslinked $\beta$-CD. The content of lactose in the control milk (without treatment by crosslinked $\beta$-CD) was 4.86%, and the amounts of lactose entrapped by crosslinked $\beta$-CD ranged from 0.00 to 0.03%. The total amounts of the entrapped short-chain free fatty acid (FFA) and free amino acid (FAA) ranged from 0.03 to 0.09 ppm and from 0.28 to $0.71{\mu}mol/mL$, respectively. The amounts of the entrapped water-soluble vitamins (L-ascorbic acid, niacin, thiamine and riboflavin) ranged from 0.02 to 0.05 ppm, 0.01 to 0.06 ppm, 0.00 to 0.06 ppm and 0.01 to 0.06 ppm, respectively. The entrapped amounts of lactose, short-chain FFAs, FAAs and water-soluble vitamins were not remarkably affected by the concentrations of crosslinked $\beta$-CD (0.4~1.2%, w/v). Only very small amounts of residual $\beta$-CD in the cholesterol-removed milk were measured (1.22~3.00 ppm). Based on the data obtained from the present study, it was concluded that the amounts of entrapped nutrients were negligible during cholesterol removal from milk by crosslinked $\beta$-CD, and only trace amounts of residual $\beta$-CD were present in cholesterol-removed milk.

Hydrophobic Cyclodextrin Derivatives as a Sustained Release Carrier of Azidothymidine (아지도싸이미딘의 지속성방출형담체로서의 소수성시클로덱스트린유도체)

  • Seo, Bo-Youn;Park, Gee-Bae;Lee, Kwang-Pyo
    • Journal of Pharmaceutical Investigation
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    • v.26 no.2
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    • pp.71-82
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    • 1996
  • This study has been undertaken to evaluate hydrophobic cyclodextrin(CD) derivatives as a sustained release carrier of azidothymidine(AZT), AZT, which has potent activity against AIDS and AIDS-related complex as thymidine analogue, has been reported that it has significant toxicity and short half life. Therefore, it is necessary to design sustained release oral dosage form to avoid undesirable side effects attributable to an excessive plasma concentration and to reduce the frequency of administration of AZT. Inclusion complexes of AZT with $acetyl-{\beta}-cyclodextrin\;(AC{\beta}CD)$ and $triacetyl-{\beta}-cyclodextrin(TA{\beta}CD)$ were prepared by solvent evaporation method. Interactions of AZT with CD were investigated by Differential Scanning Calorimetry(DSC) and Infrared Spectrophotometry(IR). The decreasing order of water solubilities of AZT and AZT-CD inclusion complexes were as follows; $AZT\;(27.873{\pm}0.015,mg/ml)\;>\;AZT-AC{\beta}CD\;(3.377{\pm}0.003)\;>\;AZT-TA{\beta}CD\;(2.528{\pm}0.001)$. Partition coefficients of $AZT-AC{\beta}CD\;and;\AZT-TA{\beta}CD$ inclusion complexes were increased by 1.27-fold, 1.54-fold in pH 1.2 and 1.32-fold, 1.47-fold in pH 6.8 in comparison with that of AZT. The mean dissolution time (MDT, min) which represents the rapidity of dissolution rate of AZT, $AZT-AC{\beta}CD,\;AZT-TA{\beta}CD$ were 5.12, 14.02 and 19.38 min in pH 1.2 and 2.52, 15.19 and 18.19 min in pH 6.8. AZT was very rapidly and completely dissolved in pH 1.2 and pH 6.8 within 5 minutes. But AZT-CD inclusion complexes showed the sustained release pattern in comparison with AZT alone. The simultaneous in situ nasal and jejunal recirculation study to compare the intrinsic absorptivity and the property of absorption sites revealed that the absorption of $AZT-TA{\beta}CD\;(N:35.35{\pm}1.08%,\;J:27.47{\pm}1.18%)$ was more than that of $AZT\;(N:16.89{\pm}2.25%,\;J:15.86{\pm}2.33%)$. The above results suggest that $TA{\beta}CD$ which is a hydrophobic cyclodextrin may serve as sustained release carrier with absorption enhancing effect.

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Synthesis of 2-Arylbenzothiazoles Catalyzed by Biomimetic Catalyst, β-Cyclodextrin

  • Londhe, Balaji S.;Pratap, Umesh R.;Mali, Jyotirling R.;Mane, Ramrao A.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2329-2332
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    • 2010
  • Cyclocondensation of 2-aminothiophenol and aryl/heteryl aldehydes has been carried using biomimetic catalyst, $\beta$-Cyclodextrin in water and obtained 2-aryl/heteryl benzothiazoles with better to excellent yields. This biomimetic catalyzed route is simple, economic, and environmentally benign.

Simultaneous Chiral Discrimination of Nine Non-Steroidal Antiinflammatory Drugs by Cyclodextrin-Modified Capillary Electrophoresis in Normal and Reversed Polarity Modes

  • Kim, Ji-Yung;La, Sook-Ie;Kim, Jung-Han;Kim, Kyoung-Rae
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.276.2-276.2
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    • 2003
  • Simultaneous enantioseparation of nine racemic non-steroidal antiinflammatory drugs (NSAIDs) for their accurate chiral discrimination was achieved by cyclodextrin (CO) modified capillary electrophoresis in the normal polarity (NP) mode and in the reversed polarity (RP) mode. The NP mode employed neutral tri-O-methyl-${\beta}$-cyclodextrin (TM${\beta}$CD) as a selector dissolved in MES buffer (PH 6.0). (omitted)

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