67217-55-4Relevant articles and documents
Influence of degree of substitution on the host-guest inclusion complex between ionic liquid substituted β-cyclodextrins with 2,4-dichlorophenol: An electrochemical, NMR and molecular docking studies
Rasdi, Fairuz Liyana Mohd,Rahim, Nurul Yani,Hasim, Fara Wahida,Prabu, Samikannu,Jumbri, Khairulazhar,Manan, Ninie Suhana Abdul,Mohamad, Sharifah
, (2019)
A mono- and di-substituted ionic liquid-β-cyclodextrin (β-CD-ILs) were synthesized and their host-guest inclusion complex with 2, 4-dichlorophenol (2,4-DCP) were evaluated by electrochemical study. First, both β-CD-ILs which is β-CD-1-BIMOTs and β-CD-2-BIMOTs were fabricated on carbon paste electrode (CPE) for determination of 2,4-DCP. The cyclic voltammetry results indicate that both β-CD-IL/CPEs exhibit higher oxidation peak current compared to native β-CD/CPE. Both complexes possess high sensitivity, stability and reproducibility. However, as the degree of substitution of ionic liquid (IL) increases, the selectivity of β-CD-IL towards 2,4-DCP decreases. Thus, it can be deduced that the degree of substitution of IL is influencing the host-guest inclusion complex of β-CD-ILs with 2,4-DCP.
Preparation of 2D molecularly imprinted materials based on mesoporous silicas via click reaction
Xu, Zhifeng,Deng, Peihong,Tang, Siping,Kuang, Daizhi,Zhang, Fuxing,Li, Junhua
, p. 8418 - 8426 (2014)
The two-dimensional (2D) molecular imprinting approach has attracted extensive research interest in recent years due to its potential advantages such as simple construction, fast template removal and rapid mass transfer. In this study, a new 2D imprinting
Biotinylated cyclooligosaccharides for paclitaxel solubilization
Cho, Eunae,Jung, Seunho
, (2018)
The poor water solubility of paclitaxel causes significant problems in producing cancer therapeutic formulations. Here, we aimed to solubilize paclitaxel using biocompatible cyclic carbohydrates. Generally recognized as safe, labeled β-cyclodextrin (β-CD), a cyclic α-1,4-glucan consisting of seven glucoses, was prepared, and bio-sourced cyclosophoraoses (CyS), which are unbranched cyclic β-1,2-glucans with 17–23 glucose units, were purified using various chromatographic methods from Rhizobium leguminosarum cultural broth. For effective targeting, CyS and β-CD were modified with a biotinyl moiety in a reaction of mono-6-amino CyS and mono-6-amino-β-CD with N-hydroxysuccinimide ester of biotinamidohexanoic acid. Interestingly, the aqueous solubility of paclitaxel was enhanced 10.3- and 3.7-fold in the presence of biotinyl CyS and biotinyl β-CD, respectively. These findings suggest that biotin-appended cyclooligosaccharides can be applied to improve the delivery of paclitaxel.
Supramolecular poly(N-acryloylmorpholine)-b-poly(D,L-lactide) pseudo-block copolymer via host-guest interaction for drug delivery
Ramesh, Kalyan,Anugrah, Daru Seto Bagus,Lim, Kwon Taek
, p. 12 - 21 (2018)
In the present study, a pseudo-block copolymer was prepared from β-cyclodextrin terminated poly(N-acryloylmorpholine) (β-CD-PNAM) and adamantine-terminated linear poly(D,L-lactide) (AD-PDLLA), through host-guest interaction between β-CD and AD groups. Ini
Efficient synthesis of pure monotosylated beta-cyclodextrin and its dimers
Tripodo, Giuseppe,Wischke, Christian,Neffe, Axel T.,Lendlein, Andreas
, p. 59 - 63 (2013)
6-O-Monotosyl-β-cyclodextrin (mono-Ts-βCD) is one of the most important intermediates in the production of substituted βCD. So far, performing the monotosylation reaction and, in particular, the purification steps was challenging, relied on toxic solvents
Novel supramolecular liquid crystals: Cyclodextrin-triphenylene column liquid crystals based on click chemistry
Yang, Fafu,Zhang, Yingmei,Guo, Hongyu
, p. 2275 - 2279 (2013)
Three new cyclodextrin-triphenylene derivatives 6, 7a and 7b were designed and synthesized by introducing a triphenylene unit into cyclodextrin based on click chemistry and further acylation of hydroxyl groups of the cyclodextrin unit. The column liquid c
Magnetic poly(β-cyclodextrin-ionic liquid) nanocomposites for micro-solid phase extraction of selected polycyclic aromatic hydrocarbons in rice samples prior to GC-FID analysis
Boon, Yih Hui,Mohamad Zain, Nur Nadhirah,Mohamad, Sharifah,Osman, Hasnah,Raoov, Muggundha
, p. 322 - 332 (2019)
Poly(β-cyclodextrin functionalized ionic liquid) immobilized magnetic nanoparticles (Fe3O4@βCD-Vinyl-TDI) as sorbent in magnetic μ-SPE was developed for the determination of selected polycyclic aromatic hydrocarbons (PAHs) in rice samples coupled with gas chromatographic-flame ionization detector (GC-FID). The nanocomposite was characterized by various tools and significant parameters that affected the extraction efficiency of PAHs were investigated. The calibration curves were linear for the concentration ranging between 0.1 and 500 μg kg?1 with correlation determinations (R2) from 0.9970 to 0.9982 for all analytes. Detection limits ranged at 0.01–0.18 μg kg?1 in real matrix. The RSD values ranged at 2.95%–5.34% (intra-day) and 4.37%–7.05% (inter-day) precision for six varied days. The sorbents showed satisfactory reproducibility in 2.9% to 9.9% range and acceptable recovery values at 80.4%–112.4% were obtained for the real sample analysis. The optimized method was successfully applied to access content safety of selected PAHs for 24 kinds of commercial rice available in Malaysia.
Effects of β-cyclodextrin-based Schiff-base Zn(II) complexes: synthesis, physicochemical characterization and their role in alleviating oxidative stress related disorder
Das, Ananya,Dutta, Somit,Sinha, Biswajit
, p. 3731 - 3747 (2018)
Two water-soluble zinc(II) complexes of β-cyclodextrin-based Schiff bases, viz., mono-6-deoxy-6-(4-(5-chloro-2-hydroxybenzylideneamino)-3,4-diaminotolune)-β-cyclodextrin (4a) and mono-6-deoxy-6-(4-(5-nitro-2-hydroxybenzylideneamino)-3,4-diaminotolune)-β-c
Supramolecular ABC miktoarm star terpolymer based on host-guest inclusion complexation
Huan, Xiuying,Wang, Dali,Dong, Ruijiao,Tu, Chunlai,Zhu, Bangshang,Yan, Deyue,Zhu, Xinyuan
, p. 5941 - 5947 (2012)
A facile strategy for the construction of supramolecular star-shaped ABC terpolymer was proposed and realized via the molecular recognition between β-cyclodextrin- (β-CD-) based host and adamantane- (AD-)modified guest. In the first step, β-CD with two di
A supramolecular strategy to assemble multifunctional viral nanoparticles
Chen, Limin,Zhao, Xia,Lin, Yuan,Huang, Yubin,Wang, Qian
, p. 9678 - 9680 (2013)
Using a one-pot approach driven by the supramolecular interaction between β-cyclodextrin and adamantyl moieties, multifunctional viral nanoparticles can be facilely formulated for biomedical applications. The Royal Society of Chemistry 2013.
Synthesis and comparative lectin-binding affinity of mannosyl-coated β-cyclodextrin-dendrimer constructs
Baussanne,Benito,Mellet,Fernandez,Law,Defaye
, p. 1489 - 1490 (2000)
Targeted drug delivery systems have been built from β-cyclodextrin by monoconjugation with mannosyl-coated dendritic branches following an iterative thiourea-forming convergent strategy; the multivalent adducts showed high Concanavalin A lectin binding ability and intact inclusion capabilities.
A plug and socket approach for tightening polyelectrolyte multilayers
Lin, Cen,Stedronsky, Erwin R.,Jordan, Luke R.,Wittenberg, Nathan J.,Regen, Steven L.
, p. 9769 - 9772 (2018)
A plug and socket approach for tightening polyelectrolyte multilayers is introduced based on the use pendant β-cyclodextrin groups. Prototypical multilayers derived from poly(sodium 4-styrene sulfonate) and β-cyclodextrin-containing poly(4-vinylbenzyltrim
Harnessing the energy of molecular recognition in a nanomachine having a photochemical on/off switch
Coulston, Roger J.,Onagi, Hideki,Lincoln, Stephen F.,Easton, Christopher J.
, p. 14750 - 14751 (2006)
6A-Deoxy-6A-(N-methyl-3-phenylpropionamido)-β-cyclodextrin operates as a molecular machine, where the amide group serves as a torsion bar to harness the work output resulting from extraction of 1-adamantanol and consequent complexati
Functionalization of cyclodextrins with N-hydroxyphthalimide moiety: A new class of supramolecular pro-oxidant organocatalysts
Melone, Lucio,Petroselli, Manuel,Pastori, Nadia,Punta, Carlo
, p. 15881 - 15892 (2015)
N-hydroxyphthalimide (NHPI) is an organocatalyst for free-radical processes able to promote the aerobic oxidation of a wide range of organic substrates. In particular, NHPI can catalyze the hydroperoxidation of polyunsaturated fatty acids (PUFA). This pro
Supramolecular intracellular delivery of an anionic porphyrin by octaarginine-conjugated per-O-methyl-β-cyclodextrin
Kitagishi, Hiroaki,Chai, Fumihiko,Negi, Shigeru,Sugiura, Yukio,Kano, Koji
, p. 2421 - 2424 (2015)
A convenient and efficient method for intracellular delivery of a water-soluble anionic porphyrin has been developed by utilizing its supramolecular interaction with per-O-methyl-β-cyclodextrin bearing an octaarginine chain as a cell-penetrating peptide.
β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers
Rahim, Nurul Yani,Tay, Kheng Soo,Mohamad, Sharifah
, p. 303 - 315 (2016)
Two covalently bonded β-Cyclodextrin (β-CD) based CSPs were prepared by immobilizing the native β-CD and mono-6-deoxy-6-(3-benzylimidazolium tosylate)-β-CD (β-CD-BIMOTs) onto modified silica gel. β-CD-BIMOTs is a β-CD based CSP with ionic liquid (3-benzylimidazolium tosylate) substituent. The enantioseparation capability of the synthesized CSPs was examined using 4 racemic mixtures of β-blockers (propranolol, metoprolol, pindolol and atenolol). The results indicated that β-CD-BIMOTs based CSP afforded more favorable enantioseparations than native β-CD based CSP. In order to study the mechanism of enantioseparation, inclusion complexes β-CD-BIMOTs and β-blockers were prepared and these inclusion complexes were characterized by using 1H NMR and NOESY. In addition, the separation conditions such as pH and composition of mobile phase were varied to study the role of β-CD and ionic liquid in enantioseparation. In general, it can be concluded that the complete enantioseparation of propranolol and metoprolol is achieved through the formation of inclusion complex with β-CD-BIMOTs and the formation π-π interaction with the ionic liquid moiety of β-CD-BIMOTs. The result also showed the poor enantioseparation of pindolol and atenolol on the β-CD-BIMOTs based CSP due to the strong interaction at the exterior torus of β-CD-BIMOTs.
Comparative studies on molecular induced aggregation of hepta-imidazoliumyl-β-cyclodextrin towards anionic surfactants
Zhao, Di,Chen, Yong,Liu, Yu
, p. 829 - 833 (2015)
A β-cyclodextrin derivative bearing seven cationic arms and its singly charged analogue, i.e., per-6-deoxy-6-(1-methylimidazol-3-ium-3-yl)-β-cyclodextrin (3) and mono-6-deoxy-6-(1-methylimidazol-3-ium-3-yl)-β-cyclodextrin (4) were synthesized and fully characterized. Their induced aggregation behaviours towards two anionic surfactant, that is, sodium dodecyl sulfonate (SDS) and dioctyl sodium sulfosuccinate (Aerosol OT, AOT), were investigated by UV-vis, NMR, Zeta-potential, dynamic light scattering (DLS), and transmission electron microscopy. The results revealed that host 3 can induce the molecular aggregation of anionic surfactant at concentration far lower than its original CAC, leading to the larger diameter, the narrower size distribution and the higher thermal stability of the induced aggregate towards the anionic surfactant possessing more hydrophobic tails.
Poly(N-vinylpyrrolidone) bearing covalently attached cyclodextrin via click-chemistry: Synthesis, characterization, and complexation behavior with phenolphthalein
Trellenkamp, Taina,Ritter, Helmut
, p. 5538 - 5543 (2010)
We report about modification of poly(N-vinylpyrrolidone) (PVP) with monofunctional β-cyclodextrin (βCD) via click-chemistry. The modification was carried out by copper(I)-catalyzed microwave-assisted Huisgen-type cycloaddition of 3-propargyl-N-vinylpyrrol
A new hyaluronan modified with β-cyclodextrin on hydroxymethyl groups forms a dynamic supramolecular network
Kova?evi?, Jelica,Prucková, Zdeňka,Pospí?il, Tomá?,Ka?párková, Věra,Rouchal, Michal,Vícha, Robert
, (2019)
A new hyaluronan derivative modified with β-cyclodextrin units (CD-HA) was prepared via the click reaction between propargylated hyaluronan and monoazido-cyclodextrin (CD) to achieve a degree of substitution of 4%. The modified hyaluronan was characterize
Mono-6-deoxy-6-aminopropylamino-Β-cyclodextrin as a supramolecular catalyst for the synthesis of indolyl 1H-pyrrole via one-pot four component reaction in water
Shinde, Vijay Vilas,Jeong, Daham,Joo, Sang Woo,Cho, Eunae,Jung, Seunho
, p. 83 - 87 (2018)
We report here the synthesis of mono-6-deoxy-6-aminopropylamino-β-cyclodextrin (Pr-β-CD) as a supramolecular organic base catalyst. Pr-β-CD was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry and SEM analysis. Using this Pr-β-CD, biologically important indolyl 1H-pyrrole derivatives were synthesized with good to excellent yields in an aqueous medium via one-pot four-component reaction. Furthermore, the catalytic mechanism was elucidated in detail by using 2D NMR (ROESY), FE-SEM and FT-IR studies. The credit of the presented protocol includes the use of novel efficacious, reusable eco-friendly supramolecular carbohydrate catalyst, and precludes the use of organic solvents and column chromatography.
An attempt to synthesize the two monomers of CDTOH: Unexpected NMR and X-ray diffraction crystal analysis
Chu, Xindang,Gao, Qianqian,Li, Haiwei,Liu, Ruiwen,Ma, Xinyuan,Xiao, Sulong,Yi, Yanliang,Zhang, Jiayi,Zhang, Lihe,Zhang, Yongmin,Zhou, Demin
, (2022/01/24)
Two monomer compounds of CDTOH, 6A-deoxy-6A-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)-per-O-methylated β-cyclodextrin 4 and 6A-deoxy-6A-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl) β-cyclodextrin 7, have been syn
Biodegradable supramolecular micellesviahost-guest interaction of cyclodextrin-terminated polypeptides and adamantane-terminated polycaprolactones
Pottanam Chali, Sharafudheen,Azhdari, Suna,Galstyan, Anzhela,Gr?schel, André H.,Ravoo, Bart Jan
supporting information, p. 9446 - 9449 (2021/09/22)
Biodegradable supramolecular micelles were prepared exploiting the host-guest interaction of cyclodextrin and adamantane. Cyclodextrin-initiated polypeptides acted as the hydrophilic corona, whereas adamantane-terminated polycaprolactones served as the hydrophobic core.
Functionalization using biocompatible carboxylated cyclodextrins of iron-based nanoMIL-100
Ca?ón-Mancisidor, Walter,Carmona, Thais,Giménez-Marqués, Mónica,Gutiérrez-Cuti?o, Marlen,Hermosilla-Ibá?ez, Patricio,Mínguez Espallargas, Guillermo,Marco, José F.,Pérez, Edwin G.,Venegas-Yazigi, Diego
supporting information, (2021/10/21)
Here we report the first example of nanoMIL-100 particles modified with monomeric cyclodextrin derivatives of different length by exploiting strong interactions between non-saturated iron trimers at the external surface and carboxylate functionalities located at the end of biocompatible and flexible linkers of cyclodextrins. The main results revealed that, after the functionalization, the cyclodextrins are selectively located at the external surfaces covering the nanoparticles. Z potential measurements show that this functionalization induced changes respect to the bare nanoMIL-100 particles, however, the presence of the cyclodextrins does not modify the size neither porosity of the nanoparticles. The amount of cyclodextrins attached, investigated by thermogravimetry, increases with the length of the linker between CD cavity and nanoparticle surface, reaching up a 9 % wt. Auger spectroscopy suggested a clear predominant sp3 character after the functionalizations (vs. sp2 predominance in the unmodified nanoMIL-100). This study supposes the creation of an alternative family of hybrids based on carboxylated monomeric cyclodextrins.
