pH-Dependent Inclusion Complexation of Highly Succinylated Cyclosophoraoses with 4'-Hydroxyflavanone

Kwon, Chanho; Jung, Seunho

doi:10.5012/bkcs.2011.32.8.2791

Cited by 6 publications

(2 citation statements)

References 32 publications

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“…The average sulfate contents were 2.25 per glucose. Succinylation was carried out using succinic anhydride and 4-(dimethylamino)pyridine, and the succinate groups were attached at the C3, C4, and C6 position [99,100]. As cationic derivatives, amine functionalization was prepared by tosylation, azidation, and amination of cyclic b-(1,2) glucans [101].…”

Section: Natural and Chemical Derivatizationmentioning

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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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: Natural and Chemical Derivatizationmentioning

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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“…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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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Harvey

2015

Mass Spectrometry Reviews

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This review is the seventh update of the original article published in 1999 on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2012. General aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, and fragmentation are covered in the first part of the review and applications to various structural types constitute the remainder. The main groups of compound are oligo- and poly-saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Much of this material is presented in tabular form. Also discussed are medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. © 2015 Wiley Periodicals, Inc. Mass Spec Rev 36:255-422, 2017.

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pH-Dependent Inclusion Complexation of Highly Succinylated Cyclosophoraoses with 4'-Hydroxyflavanone

Cited by 6 publications

References 32 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

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

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

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