123155-03-3Relevant articles and documents
Synthesis, self-assembly, and drug-loading capacity of well-defined cyclodextrin-centered drug-conjugated amphiphilic A14B7 miktoarm star copolymers based on poly(ε-caprolactone) and poly(ethylene glycol)
Gou, Peng-Fei,Zhu, Wei-Pu,Shen, Zhi-Quan
, p. 934 - 943 (2010)
Novel drug-conjugated amphiphilic A14B7 miktoarm star copolymers composed of 14 poly(ε-caprolactone) (PCL) arms and 7 poly(ethylene glycol) (PEG) arms with β-cyclodextrin (β-CD) as core moiety were synthesized by the combination of controlled ring-opening polymerization (CROP) and "click" chemistry. 1H NMR, FT-IR, and SEC-MALLS analyses confirmed the well-defined A14B7 miktoarm star architecture. These amphiphilic miktoarm star copolymers could self-assemble into multimorphological aggregates in aqueous solution, which were characterized by dynamic light scattering (DLS) and transmission electron microscopy (TEM). Moreover, the drug-loading efficiency and drug-encapsulation efficiency of the drug-conjugated miktoarm star copolymers were higher than those of the corresponding non-drug-conjugated miktoarm star copolymers.
Efficient Transport of Saccharides through a Liquid Membrane Mediated by a Cyclodextrin Dimer
Ikeda, Hiroshi,Matsuhisa, Akiyuki,Ueno, Akihiko
, p. 4907 - 4910 (2003)
A new efficient system for transporting saccharides through a liquid membrane has been constructed. The transport rates of saccharides were accelerated greatly by the cyclodextrin dimer 2; by contrast, the corresponding cyclodextrin monomer 1 was not effective at mediating saccharide transport. The transport rate of D-ribose through a chloroform liquid membrane was 17 times faster when the cyclodextrin dimer 2 was used as the transporter than when the cyclodextrin monomer 1 was used. Similarly the transport rate of methyl D-galactopyranoside was 16 times faster by 2 than by 1.
Effective syntheses of per-2,3-di- and per-3-O-chloroacetyl-β-cyclodextrins: A new kind of ATRP initiators for star polymers
Guo, Zhizhang,Chen, Xingyu,Zhang, Xiao,Xin, Jianyu,Li, Jianshu,Xiao, Huining
, p. 2351 - 2353 (2010)
Selective chloroacetylations at per-2,3- and per-3-positions of β-cyclodextrin have been achieved via protection-deprotection methods. The reaction condition of pH >4 controlled by appropriate proton scavenger is essential for obtaining designed chloroacetylation degree under effective protection, as well as for high yield with less side-products. The β-cyclodextrin derivatives with 14 or 7 chloroacetyl groups are useful initiators for synthesizing star polymers with well-defined structure by atom transfer radical polymerization.
A Family of Single-Isomer Chiral Resolving Agents for Capillary Electrophoresis. 2. Hepta-6-sulfato-β-cyclodextrin
Vincent, J. Bryan,Kirby, Dawn M.,Nguyen, Thanh V.,Vigh, Gyula
, p. 4419 - 4428 (1997)
A new, hydrophilic, single-isomer charged cyclodextrin, the sodium salt of hepta-6-sulfato-β-cyclodextrin has been synthesized, characterized, and used for the capillary electrophoretic separation of the enantiomers of numerous noncharged, acidic, basic, and zwitterionic analytes. Hepta-6-sulfato-β-cyclodextrin proved to be a much stronger complexing agent for all the analytes tested, in both low-pH and high-pH background electrolytes, than the previously synthesized, moderately hydrophobic heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin. The separation selectivities of the two single-isomer, differently functionalized charged cyclodextrins often proved to be complementary. In agreement with the predictions of the charged resolving agent migration model, separation selectivity for the noncharged analytes decreased as the concentration of hepta-6-sulfato-β-cyclodextrin was increased. For acidic, basic, and zwitterionic analytes, selectivity could increase, decrease, or pass a maximum, depending on the binding strength of the enantiomers and ionic mobilities of both the complexed and noncomplexed forms of the enantiomers.
Effect of the second coordination sphere on new contrast agents based on cyclodextrin scaffolds for MRI signals
Idriss, Hussein,Estour, Francois,Zgani, Ibrahim,Barbot, Cecile,Biscotti, Anais,Petit, Samuel,Galaup, Chantal,Hubert-Roux, Marie,Nicol, Lionel,Mulder, Paul,Gouhier, Geraldine
, p. 4531 - 4534 (2013)
Two new imaging tools using polydentate cyclodextrins were obtained using an innovative synthetic strategy. For the first time the influence of hydrogen bonding interactions of the cyclodextrin free rim was studied by MRI. The positive second coordination sphere effect was then quantified.
Synthesis of 6I-amino-6I-deoxy-2I-VII,3I-VII-tetradeca-O-methyl-cyclomaltoheptaose.
Carofiglio, Tommaso,Cordioli, Matteo,Fornasier, Roberto,Jicsinszky, Laszlo,Tonellato, Umberto
, p. 1361 - 1366 (2004)
The preparation of 6(I)-amino-6(I)-deoxy-2(I-VII),3(I-VII)-tetradeca-O-methyl-cyclomaltoheptaose is reported. Two different routes (A and B), both starting from beta-cyclodextrin (betaCD), have been examined. Route A involved: (i) synthesis of heptakis(6-
A click chemistry route to 2-functionalised PEGylated and cationic β-cyclodextrins: Co-formulation opportunities for siRNA delivery
O'Mahony, Aoife M.,Ogier, Julien,Desgranges, Stephane,Cryan, John F.,Darcy, Raphael,O'Driscoll, Caitriona M.
, p. 4954 - 4960 (2012)
A new approach to the synthesis of amphiphilic β-cyclodextrins has used 'click' chemistry to selectively modify the secondary 2-hydroxyl group. The resulting extended polar groups can be either polycationic or neutral PEGylated groups and these two amphiphile classes are compatible in dual cyclodextrin formulations for delivery of siRNA. When used alone with an siRNA, a cationic cyclodextrin was shown to have good transfection properties in cell culture. Co-formulation with a PEGylated cyclodextrin altered the physicochemical properties of nanoparticles formed with siRNA. Improved particle properties included lower surface charges and reduced tendency to aggregate. However, as expected, the transfection efficiency of the cationic vector was lowered by co-formulation with the PEGylated cyclodextrin, requiring future surface modification of particles with targeting ligands for effective siRNA delivery.
Synthesis of a β-cyclodextrin derivate and its molecular recognition behavior on modified glassy carbon electrode by diazotization
Wang, Xiuhua,Fan, Hao,Zhang, Fan,Qi, Yantao,Qiu, Wenwei,Yang, Fan,Tang, Jie,He, Pingang
, p. 7815 - 7820 (2010)
A novel β-cyclodextrin (β-CD) derivative containing mono-phenylamino (MPA-β-CD) was newly synthesized by classical Mitsunobu reaction in good yield, and its structure has been confirmed by 1H NMR, 13C NMR and electrospray ionization
Amino acid derivatives of β-cyclodextrin
Ashton, Peter R.,Koeniger, Rainer,Stoddart, J. Fraser,Alker, David,Harding, Valerie D.
, p. 903 - 908 (1996)
The syntheses of the heptaamino acid-substituted β-cyclodextrins per-6-[(phenylalanyl)amino]-β-cyclodextrin (6), per-6-cysteinyl-β-cyclodextrin (7), as well as the per-2,3-dimethyl-per-6-cysteinyl-β-cyclodextrin (12) are described. The amino acids were coupled to the primary face of the β-cyclodextrin torus using the backbone carboxylic acid functionality of phenylalanine and the side chain thiol group of cysteine. In the case of the heptacysteinyl derivatives, polyzwitterionic compounds were obtained and shown to be highly water soluble.
Contrastive study on β-cyclodextrin polymers resulted from different cavity-modifying molecules as efficient bi-functional adsorbents
Bai, Lan,Hu, Chunyan,Jiang, Wei,Li, Lei,Qin, Xiaomei,Song, Fei,Wang, Yuzhong,Wei, Qikun
, (2020)
The adsorption capacity of existing β-CD-based adsorbents is generally restrained by the limited dimension of β-CD's inherent cavity. To find an effective way to expand the inclusion/adsorption capacity of β-CD, a series of N-containing groups, amine with straight chain, imidazole with rigid five-membered ring and pyridine with rigid six-membered ring, are firstly utilized to alkylate the secondary rim of β-CD through the thiol-Michael addition. The capsulation ability of the resultant β-CD derivatives are compared and the β-CD derivatives appended with aromatic imidazole or pyridine provide extremely rich host surroundings for loading Rhodamine B (RB), which is identified by the 1H NMR titration and UV–Vis spectroscopy. The bi-functional adsorbents correlative to those β-CD derivatives are then synthesized by the polymerization of vinylated β-CD and the corresponding vinyl N-containing monomers, and applied to remove RB and Cd (II) from the aqueous condition. Governed by multiple factors such as porosity, surface charge and binding affinity, the imidazole modified β-CD adsorbent revealed the best adsorption efficiency for organic dyes and metal ions, in both single- and bi-component solutions. Our work provides effective strategy and reliable basis for the design and fabrication of β-CD-based materials with high capacity and multi-functionality.
