Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis

Jeon, Yukyoung; Kwon, Chanho; Cho, Eunae; Jung, Seunho

doi:10.1016/j.carres.2010.08.009

Cited by 26 publications

(14 citation statements)

References 22 publications

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“…Using highly sulfated cyclic b-(1,2) glucans, basic chiral drugs were separated via strong ionic interactions on the CE system, and some chiral flavonoids were successfully visualized in micellar electrokinetic chromatography [98,116]. For the stereoisomeric separation of flavonoids, carboxymethyl cyclic b-(1,2) glucans were more effective as a novel chiral selector than sulfated ones [63].…”

Section: Chirotechnologymentioning

confidence: 99%

“…In the case of extracellular glucans, 3 volumes of ethanol were added to the concentrated culture supernatant to precipitate high molecular weight exopolysaccharides [62]. After centrifugation, the supernatant was concentrated and the product was collected by adding 7-10 volumes of ethanol [62,63]. The precipitates were dissolved in water and subjected to size exclusion and ion-exchange chromatographic techniques.…”

Section: History Biosynthesis and Purificationmentioning

confidence: 99%

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Properties and current applications of bacterial cyclic β-glucans and their derivatives

Cho

Jeong

Choi

et al. 2016

J Incl Phenom Macrocycl Chem

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Cyclic b-glucans are unique constituents that are found in the periplasmic space and extracellular media of Agrobacterium, Rhizobium, Bradyrhizobium, Rhodobacter, Xanthomonas, and Ralstonia species. Based on their glycosidic linkages, they are classified into three groups composed of cyclic b-(1,2), b-(1,3)-b-(1,6), and b-(1,2)-a-(1,6) linked glucans. Their degrees of polymerization vary ranging from 10 to 40 glucose residues, and the backbone structure can be modified with non-sugar moieties. Since the macrocyclic oligosaccharides possess their own characteristics such as inherent three-dimensional structures, hydrogen bonding, and complex-forming abilities, various possible applications would be of interest in the field of green chemistry, separation science, pharmaceutical, and food industries. In this review, we have addressed the properties and current applications of bio-sourced cyclic bglucans and their derivatives.

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Section: Chirotechnologymentioning

confidence: 99%

Section: History Biosynthesis and Purificationmentioning

confidence: 99%

Properties and current applications of bacterial cyclic β-glucans and their derivatives

Cho

Jeong

Choi

et al. 2016

J Incl Phenom Macrocycl Chem

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“…The derivative was applied to the enantioseparation of dansyl-amino acids. Carboxymethylated cyclosophoraose, cyclic β-(1→2)-Dglucans composed of 17-24 units, were prepared and applied as chiral selectors [63]. Cyclosopharose was produced by Rhizobium trifolii TA-1 and derivatized with monochloro- The macrolide antibiotics erythromycin lactobionate and azithromycin as well as the acylaminoglycoside antibiotic clindamycin phosphate were evaluated as chiral selectors in CE.…”

Section: New Chiral Selectors and Mechanistic Modelsmentioning

confidence: 99%

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Scriba

2011

Bioanal Rev

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Capillary electromigration techniques are often considered ideal methods for enantioseparations due to their high separation selectivity and flexibility. Thus, numerous methods employing a chiral selector as pseudostationary phase in a background electrolyte have been developed and applied for the chiral analysis of drugs in bulk ware, pharmaceutical formulations and biological matrices. Furthermore, electromigration techniques have been combined with spectroscopic methods such as nuclear magnetic resonance in order to understand the complexation of analytes by chiral selectors. The present review focuses on recent developments and applications of chiral electromigration techniques in pharmaceutical and biomedical analysis including examples illustrating analyte-selector complex formation or mechanistic studies which have been published between January 2009 and July 2011. Selector-mediated chiral separations clearly dominate while no applications of capillary electrochromatography to pharmaceutical or biomedical analysis have been reported during this period of time.

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“…In addition, Cys have been combined with ergosterol, paclitaxel, naproxen, and luteolin to form inclusion complexes [10][11][12][13][14]. In a recent report, to expand the potential application of Cys, the hydroxyl group of Cys has been modified to various functional groups, including carboxymethyl, sulfonyl, succinyl, and butyryl groups [15][16][17][18][19][20][21]. In particular, butyryl Cys possessed a degree of substitution (DS) of 10, and thus, isoflavones/ butyryl Cys complex was formed due to the hydrophobicity of the butyryl group [21].…”

Section: Introductionmentioning

confidence: 99%

Enhanced solubility of galangin based on the complexation with methylated microbial cyclosophoraoses

Kim

Choi

et al. 2013

J Incl Phenom Macrocycl Chem

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Methylated cyclosophoraoses (M-Cys) were synthesized by reaction using dimethyl sulfate with native Cys (unbranched cyclic b-1,2-D-glucans) isolated from Rhizobium leguminosarum biovar viciae VF-39. Its structure was proven using nuclear magnetic resonance ( 1 H NMR) spectroscopy, Fourier-transform infrared (FT-IR) spectroscopy, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Based on the enhanced hydrophobicity by methylation of Cys, we investigated the inclusion property with the water-insoluble flavonoid, galangin, through a phase solubility study using ultraviolet-visible spectroscopy. The solubility of galangin was enhanced 5.6-fold according to the added concentrations (1 mM) of M-Cys, compared to the 1.9-fold and 3.4-fold enhancements by b-Cyclodextrin (b-CD) and heptakis (2,6-di-O-methyl)-b-cyclodextrin (DM-b-CD), respectively. M-Cys was also shown to have the highest binding constant (5,534 M -1 ) with galangin among the tested host molecules (b-CD, DM-b-CD, Cys, and M-Cys). From this result, we can infer that the complex of galangin with M-Cys is more stable than any of the other host molecules. The continuous variation method showed that the galangin/M-Cys complex was suitable for 1:1 stoichiometry. The formation of the complex was confirmed with 1 H NMR, FT-IR, differential scanning calorimetry, and scanning electron microscopy. Furthermore, the hypothetical molecular model of 1:1 galangin/M-Cys complex was suggested by molecular docking simulations. The cytotoxicity to the human cervical adenocarcinoma cell lines was enhanced by the galangin/M-Cys complex compared with free galangin. The obtained results indicate that M-Cys can be utilized as an effective complexing agent for galangin.

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Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis

Cited by 26 publications

References 22 publications

Properties and current applications of bacterial cyclic β-glucans and their derivatives

Properties and current applications of bacterial cyclic β-glucans and their derivatives

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Enhanced solubility of galangin based on the complexation with methylated microbial cyclosophoraoses

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