• Title/Summary/Keyword: Methyl-${\beta}$-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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Effect of Methyl-Beta-Cyclodextrin (MBCD) on Cryopreservation of Bull Spermatozoa (소 정액의 동결 보존시 Methyl-Beta-Cyclodextrin (MBCD)의 영향)

  • Lee, Kyung-Jin;Seo, Gi-Beom;Lee, Yong-Seung;Yoo, Han-Jun;Cheong, Hee-Tae;Lee, Seung-Hwan;Yang, Boo-Keun;Park, Choon-Keun
    • Reproductive and Developmental Biology
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    • v.35 no.3
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    • pp.295-300
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    • 2011
  • The objective of this study was to evaluate efficiency of methyl-beta-cyclodextrin (MBCD) in the sperm preservation of bull. For this study, the freezing of diluted semen were added with Triladyl containing 20% egg-yolk and/or 0, 1, 5, 10 and 20 mM MBCD before freezing process. Analysis of viability in frozen-thawed sperm was estimated by SYBR14/PI double stain, hypoosmotic swelling test(HOST) and acrosome damage with FITC-PNA, and mitochondria activation with Rhodamin123 by flow-cytometry. The sperm viability was significantly in 0 mM and 5 mM concentrations of MBCD than other groups (p<0.05). However, the HOST was significantly lower at 20 mM concentration of MBCD than other concentrations (p<0.05). In addition, acrosome damage and mitochondria activation rates were significantly lower at 20 mM concentration of MBCD than other groups (p<0.05). In conclusion, the viability of sperm was not significantly different among concentrations of MBCD 0, 5 and 10 mM, but MBCD 20 mM was significantly lower than other groups. In addition, as concentrations of MBCD was high, HOST, acrosome damage and mitochondria activation rates had a negative effect in bull sperm.

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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Anti-Proliferative Effects of β-Cyclodextrin Inclusion Complexes with Coumarinolignans from Acer mono (고로쇠 Coumarinolignan의 β-Cyclodextrin 포접화합물 제조 및 암세포증식 억제활성)

  • Yim, Soon-Ho;Jung, Da-Woon;Williams, Darren R.;Geckeler, Kurt E.;Kim, Kyung Keun;Shin, Boo Ahn;Lee, Ik-Soo;Kim, Huyn Jung
    • 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.

Effects of Methyl-Beta-Cyclodextrin (MBCD) on Cold Shock and Membrane Cholesterol Quantity during the Freezing Process of Miniature Pig Spermatozoa (미니돼지 정액 동결 시 Methyl-Beta-Cyclodextrin (MBCD)이 냉각 충격과 막 콜레스테롤량에 미치는 영향)

  • Lee, Sung-Young;Lee, Yong-Seung;Cheong, Hee-Tae;Yang, Boo-Keun;Park, Choon-Keun
    • Reproductive and Developmental Biology
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    • v.35 no.3
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    • pp.265-271
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    • 2011
  • This study was undertaken to find out the effect of methyl-beta-cyclodextrin (MBCD) on cold shock and membrane cholesterol quantity of sperm during the freezing process in miniature pigs. For this study, semen ejaculated from PWG M-type miniature pig was diluted that freezing solution (with egg yolk group) and m-Modena B (without egg yolk group) treated with 0, 1, 5, 10 and 20 mM MBCD before freezing process. The diluted semen was monitored sperm ability at room temperature, after cooled until $5^{\circ}C$ and after forzen-thawed for cold shock test of spermatozoa. Also, membrane cholesterol of sperm was extracted by folch solution at the same time sperm ability was assessed for viability and acrosomal status. The membrane cholesterol quantity was measured by thin-layer chromatography (TLC) method. The result, viability and acrosome integrity in semen diluted without egg yolk groups were decreased at all temperature range by increasing of MBCD concentration. In particular, sperm of egg yolk group was showed that significantly higher viability and lower acrosome damage when treated with 5 mM MBCD (p<0.05). The results of TLC experiment, cholesterol amounts were increased with MBCD cocentration in egg yolk, and decreased with MBCD concentration in m-Modena B. In cryopreservation efficiency, there was no significant difference at viability, and acrosomal state of sperm in 5 mM MBCD concentration was significantly lower in acrosome damage than other groups (p<0.05). Therefore, the addition MBCD in egg yolk was protected spermatozoa from cold shock injury. This protective effect of MBCD may be due to addition of sperm membrane cholesterol.

Changes of Aroma Compounds during Kimchi Powder Production and Encapsulation Effect of β-Cyclodextrin (김치 감압건조 시 향기성분의 변화 및 β-cyclodextrin의 향기성분 포집효과)

  • Eom, Hyun-Ju;Yoo, Ki-Seon;Yim, Chang Youn;Joo, Seoungjo;Han, Jinhee;Jin, Qing;Yoon, Hyang-Sik;Han, Nam Soo
    • Food Engineering Progress
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    • v.13 no.3
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    • pp.190-194
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    • 2009
  • The aim of this study was to investigate the change of volatile aroma compounds in kimchi during fermentation, before and after drying process. Also, the encapsulation effect of cyclodextrin on volatiles during the drying process was examined. GC-MS was used for detection and identification of volatile compounds. During kimchi fermentation, in the early stage, dimethyl sulfide, carbon disulfide were detected as major compounds and after 7 days several sulfur compounds, dimethyl disulfide, methyl 2-propenyl disulfide, allyl methyl sulfide, and di-2-propenyl disulfide bacame the major volatiles. After vacuum-drying, the kimchi powder lost 11 compounds but still retained 13 volatiles of which major compounds were dimethyl sulfide, acetaldehyde and methanethiol. In order to keep volatiles in kimchi powder along with the drying process, 0.25-1.0% cyclodextrin was added in kimchi and dried-kimchi was prepared by using vacuum dryer. Cyclodextrin acted as an encapsulation agent for aroma compounds and it resulted in less loss of volatiles during drying process. Addition of cyclodextrin will permit industry-scale production of dried-kimchi powder with less loss of aroma compounds.

Debittering of Citrus Products Using ${\beta}-Cyclodextrin$ Polymer and Ultrafiltration Process (${\beta}-Cyclodextrin$ 중합체와 한외여과 공정을 이용한 감귤류의 쓴맛 성분 제거)

  • Woo, Gun-Jo;Ha, Seung-Mi
    • 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.

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Enantioseparation and Determination of Sibutramine in Pharmaceutical Formulations by Capillary Electrophoresis

  • Zhu, Hongmei;Wu, Enqi;Chen, Jianbo;Men, Chuvan;Jang, Yu-Seon;Kang, Won-Ku;Choi, Jung-Kap;Lee, Won-Jae;Kang, Jong-Seong
    • Bulletin of the Korean Chemical Society
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    • v.31 no.6
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    • pp.1496-1500
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    • 2010
  • Sibutramine enantiomers were separated successfully by capillary zone electrophoresis using substituted cyclodextrins as chiral selectors. The effects of cyclodextrin concentration, pH, voltage, buffer type, and electrolyte concentration on the migration time and resolution of enantiomers were examined. Separation of sibutramine enantiomers on an unmodified fused silica capillary (total length, 54 cm; effective length, 45 cm) was achieved using a mixed buffer of 20 mM phosphate/10 mM citrate containing either 5 mM methyl-${\beta}$-cyclodextrin (pH 4.3) or 5 mM carboxymethyl-${\beta}$-cyclodextrin (pH 6.5). Samples were injected with a pressure of 50 mbar for 5 s and were detected at a wavelength of 223 nm. The established method showed good precision and accuracy, with intra- and inter-day variations of less than 2.9 and 4.7%, respectively, and recoveries of 95.7 - 103.8%. The stability constants of (R)- and (S)-sibutramine demonstrated that the resolution of sibutramine enantiomers was attributable primarily to the difference in stability constants. When this optimized method was applied to the determination of sibutramine enantiomers in commercial drug formulations, it proved to be economical and convenient, affording sufficient accuracy, precision, and reproducibility as well as sensitivity and selectivity.

Leukotriene Synthesis in Response to A23187 Is Inhibited by Methyl-β-Cyclodextrin in RBL-2H3 Cells

  • You, Hye Jin;Seo, Ji-Min;Moon, Ji-Young;Han, Sung-Sik;Ko, Young-Gyu;Kim, Jae-Hong
    • Molecules and Cells
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    • v.23 no.1
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    • pp.57-63
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    • 2007
  • Leukotrienes (LTs) are produced by several biosynthetic enzymes including cytosolic phospholipase $A_2$ ($cPLA_2$), 5-lipoxygenase (5-LO), and 5-lipoxygenase activating protein (FLAP) in the perinuclear area. In the present study, we showed that pretreatment with methyl-${\beta}$-cyclodextrin (MβCD), a cholesterol-depleting agent, dramatically reduced the synthesis of LTs in response to A23187 in mast cells. A23187-induced LT synthesis was inhibited by pretreatment with M${\beta}$CD, and this effect was reversed when cholesterol was added. In an approach to identifying the $M{\beta}CD$-sensitive protein(s), we observed that FLAP co-localized with flotillin-1, a lipid raft marker protein, in the lipid raft-rich low-density region of sucrose gradients. In addition, electron microscopic analysis revealed that FLAP co-localized with flotillin-1. Together, these results suggest that FLAP is present in cholesterol-rich lipid raft-like domains and that its localization in these domains is critical for LT synthesis.