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.
Cyclodextrin-based enzyme models. Part I. Synthesis of a tosylate and an epoxide derived from heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin and their characterization using 2D NMR techniques. An improved route to cyclodextrins functionalized on the secondary face
Pregel,Buncel
, p. 130 - 137 (1991)
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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.
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-
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
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.
Synthesis and self-assembly of well-defined cyclodextrin-centered amphiphilic A14B7 multimiktoarm star copolymers based on poly(ε-caprolactone) and poly(acrylic acid)
Gou, Peng-Fei,Zhu, Wei-Pu,Xu, Ning,Shen, Zhi-Quan
, p. 2961 - 2974 (2010)
Novel amphiphilic A14B7 multimiktoarm star copolymers composed of 14 poly(ε-caprolactone) (PCL) arms and 7 poly(acrylic acid) (PAA) arms with β-cyclodextrin (β-CD) as core moiety were synthesized by the combination of controlled ring-opening polymerization (CROP) and atom transfer radical polymerization (ATRP). 14-Arm star PCL homopolymers (CDSi-SPCL) were first synthesized by the CROP of CL using per-6-(tert-butyl-dimethylsilyl) -β-CD as the multifunctional initiator in the presence of Sn(Oct) 2 at 125 °C. Subsequently, the hydroxyl end groups of CDSi-SPCL were blocked by acetyl chloride. After desilylation of the tert- butyldimethylsilyl ether groups from the β-CD core, 7 ATRP initiating sites were introduced by treating with 2-bromoisobutyryl bromide, which further initiated ATRP of tertbutyl acrylate (tBA) to prepare well-defined A 14B7 multimiktoarm star copolymers [CDS(PCL-PtBA)]. Their molecular structures and physical properties were in detail characterized by 1H NMR, SEC-MALLS, and DSC. The selective hydrolysis of tert-butyl ester groups of the PtBA block gave the amphiphilic A14B7 multimiktoarm star copolymers [CDS(PCL-PAA)]. These amphiphilic copolymers could self-assemble into multimorphological aggregates in aqueous solution, which were characterized by dynamic light scattering (DLS), transmission electron microscopy (TEM) and atomic force microscopy (AFM).
MRI probes based on C6-peracetate β-cyclodextrins: Synthesis, gadolinium complexation and in vivo relaxivity studies
Biscotti, Anais,Barbot, Cécile,Nicol, Lionel,Mulder, Paul,Sappei, Célia,Roux, Marie-Hubert,Déchamps-Olivier, Isabelle,Estour, Fran?ois,Gouhier, Géraldine
, p. 32 - 43 (2018)
The initial synthesis of two β-cyclodextrin derivatives bearing seven carboxylate ligands was optimized in order to improve the production of contrast agents. A speciation study using potentiometric analysis was performed on a gadolinium(III) complex. The
Synthesis of heptakis(6-O-tert-butyldimethylsilyl)cyclomaltoheptaose and octakis(6-O-tert-butyldimethylsilyl)cyclomalto-octaose
Fuegedi, Peter
, p. 366 - 369 (1989)
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Micelles via self-assembly of amphiphilic beta-cyclodextrin block copolymers as drug carrier for cancer therapy
Li, Xiufang,Liu, Hui,Li, Jianbing,Deng, Zhiwei,Li, Lingjun,Liu, Junjun,Yuan, Jing,Gao,Yang, Yanjing,Zhong
, (2019)
We developed intelligent, star-shaped amphiphilic β-cyclodextrin (β-CD) co-polymer nanocarriers to circumvent the poor drug loading and water-solubility of β-CD. The secondary hydroxyl groups of β-CD were methylated to improve solubility, and the primary hydroxyl groups were conjugated with mPEG-b-PCL-SH through disulfide linkage to amplify the hydrophobic cavity and enhance the stability of the nanocarrier. A series of amphiphilic β-CD block copolymers (CCPPs) differing in molecular weights were synthesized that could self-assemble into core-shell nanospheres measuring 50–70 nm in water. The different CCPP carriers were screened for their drug loading, encapsulation and release efficiencies, and CCPP-2 showed the highest drug loading capacity of 31.9% by weight. These nanocarriers accumulated at the tumor site through the EPR effect and released the drug in a controlled manner in the reductive tumor microenvironment, with negligible premature leakage and side effects. Therefore, CCPP-2 shows significant potential as a smart and efficient nanovehicle for anticancer drug delivery.
Amphipathic β-cyclodextrin nanocarriers serve as intelligent delivery platform for anticancer drug
Liu, Hui,Chen, Jian,Li, Xiufang,Deng, Zhiwei,Gao, Peiru,Li, Jianbin,Ren, Tao,Huang, Ling,Yang, Yanjing,Zhong, Shian
, p. 429 - 440 (2019)
A novel glutathione-responsive (GSH-responsive)star-like amphiphilic polymer (C12H25)14-β-CD-(S-S-mPEG)7 (denoted as CCSP)was designed for efficient antitumor drug delivery. The amphiphilic β-cyclodextrin (β-CD)self-polymerize in water to form a sphere with a diameter of 40–50 nm. The secondary hydroxyl groups of β-CD were modified by dodecyl to form a hydrophobic core and the primary hydroxyl groups of β-CD were decorated with PEG through disulfide bond to form a hydrophilic shell. Since the hydrophobic cavity of β-CD was maintained, the hydrophobic core formed by dodecyl as well as cavity of β-CD provided CCSP with a loading content as high as 39.6 wt%. Importantly, DOX@CCSP exhibited low drug leakage and negligible cytotoxicity in non-reductive physiological environment, while it showed rapid release and high cytotoxicity in reductive tumorous environment via the breakage of disulfide bond. In view of the above-mentioned advantages of DOX@CCSP nanocarriers such as high loading content, proper size, favorable stimulus-response release performance and low leakage, it is believed that CCSP may offer great potential to be used as an intelligent nanocarrier for anticancer drug delivery.
