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Cyclodextrin

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https://www.readbyqxmd.com/read/28548683/secondary-rim-%C3%AE-cyclodextrin-functionalization-to-conjugate-with-c60-improved-efficacy-as-photosensitizer
#1
Xiaolei Zhu, Annamaria Quaranta, René Bensasson, Matthieu Sollogoub, Yongmin Zhang
DIBAL-H-mediated demethylation provides a novel entry to secondary rim functionalized γ-CD. 2A,3B-dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows the access to the most water-soluble C60 conjugate described so far. The water-solubility 0.12 M (550 mg/mL) is 150 times higher than that of native γ-CD/ C60 complex. Its singlet oxygen (¹O₂) quantum yield is 0.39, an increase by one or two orders of magnitude compared to that of α(β)CD-C60 conjugates.
May 26, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28548311/multivalency-to-inhibit-and-discriminate-hexosaminidases
#2
Yves Bleriot, Dimitri Alvarez-Dorta, Dustin T King, Thibaut Legigan, Daisuke Ide, Isao Adachi, David Deniaud, Jerome Desire, Atsushi Kato, David Vocadlo, Sebastien Gouin
A set of multivalent polyhydroxylated acetamidoazepanes based on ethylene glycol, glucoside or cyclodextrin scaffolds was prepared. The compounds were assessed against plant, mammalian and therapeutically relevant hexosaminidases. Multimerization was shown to improve the inhibitory potency with synergy, and to fine tune the selectivity profile between related hexosaminidases.
May 26, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28546841/the-effect-of-cyclodextrin-complexation-on-the-solubility-and-photostability-of-nerolidol-as-pure-compound-and-as-main-constituent-of-cabreuva-essential-oil
#3
Joyce Azzi, Pierre-Edouard Danjou, David Landy, Steven Ruellan, Lizette Auezova, Hélène Greige-Gerges, Sophie Fourmentin
Nerolidol (Ner), a major component of many plant essential oils, is known for its various biological properties. However, the low solubility of Ner in water and its susceptibility to degradation limit its application. The aim of our study was to improve the solubility and photostability of Ner through its encapsulation in different cyclodextrins (CDs). The formation constants of cis-, trans-Ner and their commercial mixture with various CDs (α-CD, β-CD, γ-CD, HP-β-CD, RAMEB, CRYSMEB and SBE-β-CD) were determined by phase solubility studies and confirmed by the spectral displacement UV-visible method...
2017: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28546834/cyclodextrins-tethered-with-oligolactides-green-synthesis-and-structural-assessment
#4
Cristian Peptu, Mihaela Balan-Porcarasu, Alena Šišková, Ľudovít Škultéty, Jaroslav Mosnáček
Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator and the catalyst. The synthetic procedure in which CDs and L-lactide (L-LA) are reacting in bulk at relatively high temperature of 110 °C was investigated considering the structural composition of the products. The obtained products were thoroughly characterized via mass spectrometry methods with soft ionization like matrix-assisted laser desorption ionization (MALDI) and electrospray ionization (ESI)...
2017: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28546517/host-guest-interaction-of-%C3%AE-cyclodextrin-with-isomeric-ursolic-acid-and-oleanolic-acid-physicochemical-characterization-and-molecular-modeling-study
#5
Yuan Huang, Peng Quan, Yongwei Wang, Dongsheng Zhang, Mingwan Zhang, Rui Li, Nan Jiang
Ursolic acid (UA) and oleanolic acid (OA) are insoluble drugs. The objective of this study was to encapsulate them into β-cyclodextrin (β-CD) and compare the solubility and intermolecular force of β-CD with the two isomeric triterpenic acids. The host-guest interaction was explored in liquid and solid state by ultraviolet-visible absorption, 1 H NMR, phase solubility analysis, and differential scanning calorimetry, X-ray powder diffractometry, and molecular modeling studies. Both experimental and theoretical studies revealed that β-CD formed 1: 1 water soluble inclusion complexes and the complexation process was naturally favorable...
April 6, 2017: Journal of Biomedical Research
https://www.readbyqxmd.com/read/28546106/enhanced-dissolution-and-skin-permeation-profiles-of-epalrestat-with-%C3%AE-cyclodextrin-derivatives-using-a-cogrinding-method
#6
Takayuki Furuishi, Shoma Takahashi, Noriko Ogawa, Mihoko Gunji, Hiromasa Nagase, Toyofumi Suzuki, Tomohiro Endo, Haruhisa Ueda, Etsuo Yonemochi, Kazuo Tomono
Epalrestat (EPL) is a water-insoluble drug (14μM) that inhibits aldose reductase. This study investigated the interactions between β-cyclodextrin (CD) derivatives and EPL to determine the solubilizing effect on EPL from phase solubility diagrams. We improved the solubility of EPL in water by adding β-CD derivatives. Moreover, the solubility of EPL mixed with β-CD derivatives by cogrinding in a ball mill method was about 2-3 times higher than those of EPL with the same CD concentration (5mM) calculated from phase solubility diagrams...
May 22, 2017: European Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/28546070/efficient-loading-of-ethionamide-in-cyclodextrin-based-carriers-offers-enhanced-solubility-and-inhibition-of-drug-crystallization
#7
Jitendra Wankar, Giuseppina Salzano, Elisabetta Pancani, Gabor Benkovics, Milo Malanga, Francesco Manoli, Ruxandra Gref, Eva Fenyvesi, Ilse Manet
Ethionamide (ETH) is a second line antitubercular drug suffering from poor solubility in water and strong tendency to crystallize. These drawbacks were addressed by loading ETH in β-cyclodextrin (βCyD)-based carriers. The drug was incorporated in a molecular state avoiding crystallization even for long-term storage and obtaining a tenfold increased solubility up to 25mM. The binding of ETH to polymeric βCyD nanoparticles (pβCyD NPs) was investigated in neutral aqueous medium by means of solubility phase diagrams, circular dichroism (CD) and UV-vis absorption and compared with the corresponding βCyD monomer...
May 22, 2017: International Journal of Pharmaceutics
https://www.readbyqxmd.com/read/28545253/encapsulation-of-the-antioxidant-r-%C3%AE-lipoic-acid-in-permethylated-%C3%AE-and-%C3%AE-cyclodextrins-thermal-and-x-ray-structural-characterization-of-the-1-1-inclusion-complexes
#8
Mino R Caira, Susan A Bourne, Buntubonke Mzondo
The naturally occurring compound α-lipoic acid (ALA) is implicated in manifold critical biological roles and its potent antioxidant properties and potential for treatment of various diseases have led to its widespread use as a dietary supplement. However, shortcomings of poor aqueous solubility and low thermal stability have hampered its development as a medicinal agent, prompting the use of cyclodextrins (CDs) to address these problems. The paucity of published structural data on the nature of the interactions between ALA and CDs motivated the present study, which describes the synthesis and X-ray structural elucidation of crystalline inclusion complexes between the biologically relevant R-(+)-α-lipoic acid (RALA) and the host molecules permethylated α-CD (TMA) and permethylated β-CD (TMB)...
May 23, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28544461/semi-ipns-with-moisture-triggered-shape-memory-and-self-healing-properties
#9
Zhi-Chao Jiang, Yao-Yu Xiao, Yang Kang, Bang-Jing Li, Sheng Zhang
Moisture or water has the advantages of being green, inexpensive, and moderate. However, it is challenging to endow water-induced shape memory property and self-healing capability to one single polymer because of the conflicting structural requirement of the two types of materials. In this study, this problem is solved through introducing two kinds of supramolecular interactions into semi-interpenetrating polymer networks (semi-IPNs). The hydrogen bonds function as water-sensitive switches, making the materials show moisture-induced shape memory effect...
May 23, 2017: Macromolecular Rapid Communications
https://www.readbyqxmd.com/read/28544353/chiral-separation-of-12-pairs-of-enantiomers-by-capillary-electrophoresis-using-heptakis-2-3-diacetyl-6-sulfato-%C3%AE-cyclodextrin-as-the-chiral-selector-and-the-elucidation-of-the-chiral-recognition-mechanism-by-computational-methods
#10
Yaqi Yao, Peilu Song, Xiaoli Wen, Miaoduo Deng, Jian Wang, Xingjie Guo
Chiral separation of 12 pairs of basic analyte enantiomers including oxybutynin, bambuterol, tradinterol, clenbuterol, clorprenaline, terbutaline, tulobuterol, citalopram, phencynonate, fexofenadine, salbutamol and penehyclidine was conducted by capillary electrophoresis using a single-isomer anionic β-cyclodextrin derivative, heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin as the chiral selector. Parameters influencing separation were studied, including background electrolyte pH, heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin concentration, buffer concentration and separation voltage...
May 24, 2017: Journal of Separation Science
https://www.readbyqxmd.com/read/28541948/attached-%C3%AE-cyclodextrin-%C3%AE-2-3-epoxypropoxy-propyl-trimethoxysilane-to-graphene-oxide-and-its-application-in-copper-removal
#11
Zongxue Yu, Qi Chen, Liang Lv, Yang Pan, Guangyong Zeng, Yi He
The environmental applications of graphene oxide and β-cyclodextrin (β-CD) have attracted great attention since their first discovery. Novel nanocomposites were successfully prepared by using an esterification reaction between β-cyclodextrin/γ-(2,3-epoxypropoxy) propyl trimethoxysilane grafted graphene oxide (β-CD/GPTMS/GO). The β-CD/GPTMS/GO nanocomposites were used to remove the Cu(2+) from aqueous solutions. The characteristics of β-CD/GPTMS/GO were detected by scanning electron microscopy (SEM), Fourier transform infrared, X-ray diffraction (XRD), thermogravimetric analysis (TG) and energy dispersive X-ray (EDX)...
May 2017: Water Science and Technology: a Journal of the International Association on Water Pollution Research
https://www.readbyqxmd.com/read/28540941/chiral-differentiation-of-d-and-l-alanine-by-permethylated-%C3%AE-cyclodextrin-irmpd-spectroscopy-and-dft-methods
#12
Sung-Sik Lee, Soojin Park, Yin Hong, Jae-Ung Lee, Jun-Hyeok Kim, Dongkyung Yoon, Xianglei Kong, Sungyul Lee, Han Bin Oh
The gaseous chiral differentiation of alanine by permethylated β-cyclodextrin was studied using IRMPD spectroscopy and density functional theory calculations. The protonated non-covalent complexes of permethylated β-cyclodextrin and d- or l-alanine were mass-selected and investigated by IR laser pulses in the wavelength region of 2650-3800 cm(-1). The remarkably different features of the IRMPD spectra for d- and l-alanine are described, and their origin is elucidated by quantum chemical calculations. We show that the differentiation of the experimentally observed spectral features is the result of different local interactions of d- and l-alanine with permethylated β-cyclodextrin...
May 25, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28540726/sorption-and-release-of-natural-phenolic-antioxidants-in-different-cyclodextrin-polymers
#13
M García-Padial, María Cristina Martínez-Ohárriz, José Ramón Isasi, A Zornoza
The sorption and release of tyrosol and caffeic acid, two biophenolic antioxidants with known health benefits, in different insoluble cyclodextrin polymers has been studied. Cyclodextrin polymers were synthesized by cross-linking β-cyclodextrin or 50:50 w/w nominal mixtures of α- and β-cyclodextrin using either epichlorohydrin (EP) or toluene-2,4-diisocyanate (TDI) as crosslinking agents. An analogous sucrose polymer was prepared using EP as crosslinking reagent. Freundlich isotherms and isosteric heats of sorption for tyrosol and caffeic acid in the insoluble β-cyclodextrin polymer crosslinked with epichlorohydrin at 50 °C were obtained and discussed...
May 25, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28537024/absolute-configuration-of-2-2-3-3-6-pentachlorinatedbiphenyl-pcb-84-atropisomers
#14
Xueshu Li, Sean R Parkin, Hans-Joachim Lehmler
Nineteen polychlorinated biphenyl (PCB) congeners, such as 2,2',3,3',6-pentachlorobiphenyl (PCB 84), display axial chirality because they form stable rotational isomers, or atropisomers, that are non-superimposable mirror images of each other. Although chiral PCBs undergo atropselective biotransformation and atropselectively alter biological processes, the absolute structure of only a few PCB atropisomers has been determined experimentally. To help close this knowledge gap, pure PCB 84 atropisomers were obtained by semi-preparative liquid chromatography with two serially connected Nucleodex β-PM columns...
May 23, 2017: Environmental Science and Pollution Research International
https://www.readbyqxmd.com/read/28534285/development-of-self-forming-doxorubicin-loaded-polymeric-depots-as-an-injectable-drug-delivery-system-for-liver-cancer-chemotherapy
#15
Pinunta Nittayacharn, Norased Nasongkla
The objective of this work was to develop self-forming doxorubicin-loaded polymeric depots as an injectable drug delivery system for liver cancer chemotherapy and studied the release profiles of doxorubicin (Dox) from different depot formulations. Tri-block copolymers of poly(ε-caprolactone), poly(D,L-lactide) and poly(ethylene glycol) named PLECs were successfully used as a biodegradable material to encapsulate Dox as the injectable local drug delivery system. Depot formation and encapsulation efficiency of these depots were evaluated...
July 2017: Journal of Materials Science. Materials in Medicine
https://www.readbyqxmd.com/read/28533751/docetaxel-loaded-nanoparticles-assembled-from-%C3%AE-cyclodextrin-calixarene-giant-surfactants-physicochemical-properties-and-cytotoxic-effect-in-prostate-cancer-and-glioblastoma-cells
#16
Laura Gallego-Yerga, Inmaculada Posadas, Cristina de la Torre, Jesús Ruiz-Almansa, Francesco Sansone, Carmen Ortiz Mellet, Alessandro Casnati, José M García Fernández, Valentín Ceña
Giant amphiphiles encompassing a hydrophilic β-cyclodextrin (βCD) component and a hydrophobic calix[4]arene (CA4) module undergo self-assembly in aqueous media to afford core-shell nanospheres or nanocapsules, depending on the nanoprecipitation protocol, with high docetaxel (DTX) loading capacity. The blank and loaded nanoparticles have been fully characterized by dynamic light scattering (DLS), ζ-potential measurements and cryo-transmission electron microscopy (cryo-TEM). The data are compatible with the distribution of the drug between the nanoparticle core and the shell, where it is probably anchored by inclusion of the DTX aromatic moieties in βCD cavities...
2017: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/28533017/morphological-and-physicochemical-characterization-of-porous-starches-obtained-from-different-botanical-sources-and-amylolytic-enzymes
#17
Yaiza Benavent-Gil, Cristina M Rosell
Porous starches might offer an attractive alternative as bio-adsorbents of a variety of compounds. However, morphology and physicochemical properties of starches must be understood before exploring their applications. Objective was to study the action of different amylolytic enzymes for producing porous starches. Wheat, rice, potato and cassava starches were treated with Amyloglucosidase (AMG), α-amylase (AM) and cyclodextrin-glycosyltransferase (CGTase). Morphological characteristics, chemical composition, adsorptive capacity and pasting/thermal properties were assessed...
May 19, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28532835/effect-of-cholesterol-loaded-cyclodextrin-supplementation-on-tyrosine-phosphorylation-and-apoptosis-like-changes-in-frozen-thawed-hariana-bull-spermatozoa
#18
Hanuman P Yadav, Anuj Kumar, Nadeem Shah, Dharmendra S Chauhan, Atul Saxena, Sarvajeet Yadav, Dilip Kumar Swain
The beneficial effects of cholesterol loaded cyclodextrin (CLC) addition were evaluated in cryopreserved bull semen. Forty ejaculates were collected from Hariana bulls (n = 4), pooled and divided into 4 aliquots. All the aliquots were initially diluted in to egg yolk tris citrate and supplemented with CLC @ 0.5 mg (Group-II), 1.0 mg (G-III) and 2.0 mg (G-IV) CLC/120 × 10(6) spermatozoa or without CLC (G-I) that served as control. Extended semen was cryopreserved at -196 °C for 24 h. Seminal attributes like motility, viability, cryocapacitation like changes, tyrosine phosphorylation, apoptosis like changes in terms of mitochondrial transmembrane potential and DNA integrity were evaluated after equilibration and thawing...
July 1, 2017: Theriogenology
https://www.readbyqxmd.com/read/28532154/injectable-nir-ph-responsive-nanocomposite-hydrogel-as-long-acting-implant-for-chemo-photothermal-synergistic-cancer-therapy
#19
Xiaoyu Xu, Ziyuan Huang, Zeqian Huang, Xuefei Zhang, Siyu He, Xiaoqi Sun, Yifeng Shen, Mina Yan, Chunshun Zhao
In this study, Gold nanorods (GNRs) were incorporated into the hydrogel networks formed by the copolymerization of N-isopropylacrylamide (NIPAm) and methacrylated β-cyclodextrin-based macromer (MPCD) to fabricate an injectable and NIR/pH-responsive poly(NIPAm-co-MPCD)/GNRs nanocomposite hydrogel, which could serve as a long-acting implant for chemo-photothermal synergistic cancer therapy. The nanocomposite hydrogel showed superior mechanical and swelling properties, gelation characteristic and excellent NIR-responsive property...
May 23, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28532031/screening-of-process-variables-to-enhance-the-solubility-of-famotidine-with-2-hydroxypropyl-%C3%AE-cyclodextrin-pvp-k-30-by-using-plackett-burman-design-approach
#20
Umakant Verma, Jitendra B Naik, Jayesh S Patil, Sunil K Yadava
In the present work, inclusion complex of famotidine (FMT) was prepared with (2-HydroxyPropyl)-β-Cyclodextrin (HP-β-CyD) and polyvinylpyrrolidone K-30 (PVP K-30) by spray drying technique to enhance the solubility of famotidine. FMT is a potent histamine H2-receptor antagonist having low solubility as well as oral bioavailability. In order to enhance the solubility of FMT, a quality by design (QbD) approach has been used by employing Plackett-Burman design (PBD). With the application of PBD, seven independent process variables were investigated and optimized for maximum solubility...
August 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
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