• Title/Summary/Keyword: ${\alpha}-Cyclodextrin$

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Inclusion Complexation of Chlorpropamide with Cyclodextrins (클로로프로파미드와 싸이클로덱스트린과의 포접 화합물에 관한 연구)

  • 정경혜;김길수;구영순
    • 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.

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Synthesis and Characterization of Hyaluronic Acid-α-Cyclodextrin Conjugate as the Potential Carrier of PEGylated Drugs

  • Sivasubramanian, Maharajan;Park, Jae-Hyung
    • Journal of Pharmaceutical Investigation
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    • v.40 no.4
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    • pp.219-223
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    • 2010
  • The hyaluronic acid (HA) conjugate bearing $\alpha$-cyclodextrin ($\alpha$-CD) was synthesized as the potential carrier of poly(ethylene glycol) (PEG)-drug conjugates. The HA conjugate was prepared by the reaction between the carboxylic acid of HA and the primary amine of $\alpha$-CD in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and 1-hydroxybenzotriazole. The chemical structure of the conjugate was confirmed using $^1H$ NMR and FT-IR spectroscopy. The conjugate could form nano-sized particles in the presence of PEG by forming the inclusion complexes between $\alpha$-CD at the backbone of HA, which was demonstrated using electrophoretic light scattering and field emission transmission electron microscopy. It is anticipated that this novel kind of nanoparticles can serve as a useful delivery system for PEGylated drugs.

α -Cyclodextrin Modified Screen Printed Graphite Electrodes for Detection of Phenols

  • Kim, Hwa-jeong;Jang, Seung-Cheol;Shim, Yoon-Bo
    • Bulletin of the Korean Chemical Society
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    • v.23 no.3
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    • pp.427-431
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    • 2002
  • A screen printed graphite electrode has been developed for a simple and sensitive determination of phenolic compounds in an aqueous solution. The electrode developed uses a simple and effective screen printing technique with ${\alpha}-Cyclodextrin({\alpha}-CD)$ modified graphite ink. Phenols were captured on the surface of the ${\alpha}-CD$ modified electrode through complex formation. The phenol/ ${\alpha}-CD$ complex was deposited and quantified electrochemically using cyclic voltammetry (CV), differential pulse voltammetry (DPV) and square wave voltammetry (SWV). The optimization of the experimental parameters was performed in regard to electrode composition, pH, temperature, sample preconcentration time. Interferences from other organic compounds were investigated. The detection limit for phenols was 500 ${\pm}7$ nM for DPV, with the linear range of 0.5 ${\mu}M$ -25.0 ${\mu}M$ and 30 ${\pm}2$ nM for SWV, with the linear range of 30 nM - $50{\mu}M$, respectively.

Purification and Characterization of Cyclodextrin Glycosyltransferase from Bacillus brevis CD162 (Bacillus brevis CD162 Cyclodextrin Glycosyltransferase의 정제 및 특성)

  • Kim, Myung-Hee;Lim, Young-Hee;Oh, Tae-Kwang;Sohn, Cheon-Bae
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.465-471
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    • 1997
  • The cyclodextrin glycosyltransferase (CGTase, EC 3.2.1.19) from Bacillus brevis CD162 was purified by precipitating with ammonium sulfate, DEAE-Sepharose CL-6B column chromatography and Sephadex G-150 column chromatography. The molecular mass and pI of the purified enzyme were estimated to be 74,000 and 6.3 by SDS-PAGE and isoelectric focusing, respectively. The purified enzyme was clearly identified as the CGTase by zymogram after SDS-PAGE. The optimum pH and temperature for the enzyme activity were 8.0 and $55^{\circ}C$, respectively. The enzyme was stable at the range of pH $5.5{\sim}9.0$, and up to $50^{\circ}C$. The amino acid sequence from the $NH_2-terminal$ of the purified CGTase was Ser-Val-Thr-Asn-Lys-Val-Asn-Tyr-Ser-Lys-Asp-Val-Ile-Tyr-Gln. The yields of the products from starch as the substrate were 1.3% for ${\alpha}-$, 33.9% for ${\beta}-$, and 9.7% for ${\gamma}-cyclodextrin$.

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The Fluorescence Study on the Inducing Orientation of 4-Biphenyl Acetonitrile Adsorbed on Metal Colloids (금속콜로이드 표면에 흡착된 4-Biphenyl Acetonitrile의 흡착배향 유도에 관한 형광 연구)

  • Song, Won-Sik;Lee, Jun-Kyeng;Yu, Soo-Chang
    • Journal of the Korean Chemical Society
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    • v.53 no.4
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    • pp.399-406
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    • 2009
  • The fluorescence study was performed to see whether the adsorption orientation of 4-biphenyl acetonitrile(BPAN) on metal colloids can be changed by forming an inclusion complex with $\alpha$-cyclodextrin($\alpha$-CD). The fluorescence quenching was observed with increasing temperature to confirm the direct adsorption of BPAN to the Au and Ag colloidal surfaces. BPAN adsorbed on the metal colloids formed inclusion complex with $\alpha$-CD regardless of the kinds of metal colloids. The formation constants, 32 $M^{-1}$ and 13 $M^{-1}$ for Au and Ag colloids respectively, were obtained with Benesi-Hildebrand plot. The molecules adsorbed on both the Au and Ag colloidal surfaces behaved similarly to each other, leading to the conclusion that the orientation of BPAN adsorbed on the metal colloids can be modified with $\alpha$-CD.

Pharmaceutical Studies on the Inclusion Complexes of Non-Steroidal Antiinflammatory Drugs with ${\beta}-Cyclodextrin$ (I) (비(非)Steroid 성소염약물(性消炎藥物)과 ${\beta}-Cyclodextrin$과의 Inclusion Complex에 관(關)한 약제학적(藥劑學的) 연구(硏究) (제1보)(第一報))

  • Han, Kun;Lee, Min-Hwa;Kim, Shin-Keun
    • Journal of Pharmaceutical Investigation
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    • v.13 no.1
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    • pp.10-22
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    • 1983
  • The interactions of ${\alpha}-cyclodextrin({\alpha}-CyD)$ and ${\beta}-cyclodextrin({\beta}-CyD)$ with several non-steroidal antiinflammatory drugs were studied on the effects of ${\alpha}-$ and ${\beta}-CyD$ on the solubility of the drugs in aqueous medium. Indoprofen, niflumic acid, alclofenac, and naproxen were chosen as representatives of antiinflammatory drugs. The solubility of all drugs studied increased with the addition of ${\beta}-CyD$, while not with glucose or ${\alpha}-CyD$. The increase of the solubility with ${\beta}-CyD$ was considered due mainly to the formation of inclusion complexes between ${\beta}-CyD$ and drugs. From the solubility data, the apparent stability constants K of the complex could be calculated. Ultraviolet absorption and circular dichroism confirmed the inclusion of indoprofen, niflumic acid and naproxen with ${\beta}-CyD$ in the molar ratio of 1 : 1. Inclusion complexes in solid powder form were obtained by the freeze-drying method and the inclusion formation was confirmed again by infrared, diffential thermal analysis, and X-ray diffraction measurements.

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Production of 2-O--$\alpha$-D-Glucopyranosyl L-Ascorbic Acid by Cyclodextrin Glucanotransferase from Bacillus sp. JK-43 (Bacillus sp. JK-43의 Cyclodextrin Glucanotransferase에 의한 2-O-$\alpha$-D-Glucopyranosyl L-Ascorbic Acid 생산에 관한 연구)

  • 전홍기;배경미;김영희;김성구
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.29 no.1
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    • pp.49-56
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    • 2000
  • The 2-O-$\alpha$-D-glucopyranosyl L-ascorbic acid (AA-2G) which was enzymatically glucosylated with the cyclodextrin glucanotransferase (CGTase) [EC 2.4.1.19] from Bacillus sp. JK-43 has been reported previously. The presnet experiments examined the optimal conditons for the productio of AA-2G from AA and soluble starch, and characterized the properties of the CGTase from Bacillus sp. JK-43. The reaction mixture for the maximal production of AA-2G was followings; 12% total substrate concentration, 1,400 usits/mL of CGTase and a mixing ratio of 2 : 3(g or AA : g of soluble starch). Under this condition, 1.76mM of AA-2G, which corresponded to 2.53% yield based on AA, was produced after incubation for 24hrs at 45$^{\circ}C$ (pH 5.5). The optimum pH and temperature for the CGTase activity were 6.0 and 45$^{\circ}C$, respectively. The enzyme was stable at pH 5.5 to 9.5, and at temperature up to 5$0^{\circ}C$. The thermostability of the enzyme could be enhanced up to 6$0^{\circ}C$ by the addition of 30mM CaCl2.

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Synthesis of Maltosyl-$\beta$-Cyclodextrin through the Reverse Reaction of Pullulanase (Pullulanase의 Reverse Reaction을 이용한 Maltosyl-$\beta$-Cyclodextrin의 합성)

  • 한일근;이용현
    • Microbiology and Biotechnology Letters
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    • v.19 no.5
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    • pp.444-449
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    • 1991
  • Synthesis of maltosyl-$\beta$-cyclodextrin using maltose ($G_2$) and $\beta$-cyclodextrin ($\beta$-CD) as substrates through the reverse reaction of pullulanase was investigated. The optimal conditions for the condensation reaction were as below: mixing ratio of maltose to $\beta$-CD of 12.7, mixed substrate concentration of 70% (w/w, 70 g/100 ml $H_2O$), and amount of pullulanse of 350 units/100 ml. The concentration of synthesized maltosyl-P-CD concentration was reached up to 2.31 g/100 rnl at above reaction conditions, which corresponded the conversion yield of 43% (w/w, g of branched-CD/g of CD). The synthesis of maltosyl-$\alpha >\gamma >\beta$-CD was also attempted, and conversion yield was in the order of a>y>J3-CDs. Condensation reaction between various maltooligosaccharides ($G-1\sim G_6$ showed that maltose was the most effective oligorner for condensation reaction with $\beta$-CD. To increase the conversion yield various alcohols were added into the reaction mixture, amyl alcohol was found to be the most acceptable alcohol for increasement of convesion yield which increased from 43.0 to 83.0% upon addition of same volume of amyl alcohol into the reaction mixture.

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Purification and Some Properties of Cyclodextrin Hydrolase (Cyclodextrin분해효소의 정제 및 그 특성)

  • Kim, Yong-Hwi;Shim, Kyu-Kwnag;Moon, Young-Hee
    • Applied Biological Chemistry
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    • v.33 no.1
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    • pp.79-86
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    • 1990
  • Cyclodextrin hydrolase from Bacillus stearothermophilus KFCC 21203 was purified and the properties of the purified enzyme were investigated. The enzyme was purified 15 folds with 77 % recovery by ammonium sulfate fractionation, DEAE-cellulose chromatography, and Ultro AcA 34 gel filtration. The specific activity and the molecular weight of the enzyme were 1.30 units/mg protein and about 29,500, respectively, The maximum activity of the enzyme was shown at $55^{\circ}C$ and pH 5.5. However, stable temperature and pH were $40^{\circ}C$ and $5.0{\sim}8.0$, respectively. The Km value for ${\gamma}-cyclodextrin$ was $3.78{\times}10^{-3}$ M. The degradation activity of the enzyme was selectively high for ${\gamma}-cyclodextrin$, and very low for ${\beta}-cyclodextrin$, but not for ${\alpha}-cyclodextrin$. The decomposed products of ${\gamma}-cyclodextrin$ were mainly glucose and maltose, and a little mlatotriose. The activity of the enzyme was very high for amylose, potato starch, corn starch, amylopectin and maltooligomer, and relatively high for glycogen and dextrin. The decomposed products of them were mainly glucose and maltose.

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Production Enhancement of Menthol in Suspension Cultures of Peppermint Using Cyclodextrin (Peppermint 세포 현탁배양에서 Cyclodextrin을 이용한 Menthol의 생산성 증대)

  • 조규헌;임철호;박세춘;신명근
    • KSBB Journal
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    • v.13 no.1
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    • pp.26-30
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    • 1998
  • The suspension cultures of Mentha piperita produce menthol which has very low solubility in water due to its hydrophobicity. This can be considered as a factor for its low production in the suspension suspension cultures. Cyclodextrin has the hydrophobic cavity inside the molecule in which menthol can be captured and allow to form a stable complex. The suspension culture of Mentha piperita showed 70% higher production enhancement in the medium containing 1.5%(w/v) $\beta$-cyclodextrin than the control. $\beta$-cyclodextrin had no adverse effect on the cell growth and showed the best result among $\alpha$-, $\beta$- and $\gamma$-cyclodextrins tested in terms of menthol production. We demonstrated that $\beta$-cyclodextrin can be used to enhance the production of menthol in the suspension cultures by capturing hydrophobic menthol into the cavity of cyclodextrin molecules.

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