- 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)
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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.
- Gou, Peng-Fei,Zhu, Wei-Pu,Shen, Zhi-Quan
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- Efficient Transport of Saccharides through a Liquid Membrane Mediated by a Cyclodextrin Dimer
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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.
- Ikeda, Hiroshi,Matsuhisa, Akiyuki,Ueno, Akihiko
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- Effective syntheses of per-2,3-di- and per-3-O-chloroacetyl-β-cyclodextrins: A new kind of ATRP initiators for star polymers
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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.
- Guo, Zhizhang,Chen, Xingyu,Zhang, Xiao,Xin, Jianyu,Li, Jianshu,Xiao, Huining
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- A Family of Single-Isomer Chiral Resolving Agents for Capillary Electrophoresis. 2. Hepta-6-sulfato-β-cyclodextrin
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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.
- Vincent, J. Bryan,Kirby, Dawn M.,Nguyen, Thanh V.,Vigh, Gyula
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- Effect of the second coordination sphere on new contrast agents based on cyclodextrin scaffolds for MRI signals
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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.
- Idriss, Hussein,Estour, Francois,Zgani, Ibrahim,Barbot, Cecile,Biscotti, Anais,Petit, Samuel,Galaup, Chantal,Hubert-Roux, Marie,Nicol, Lionel,Mulder, Paul,Gouhier, Geraldine
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- Synthesis of 6I-amino-6I-deoxy-2I-VII,3I-VII-tetradeca-O-methyl-cyclomaltoheptaose.
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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-
- Carofiglio, Tommaso,Cordioli, Matteo,Fornasier, Roberto,Jicsinszky, Laszlo,Tonellato, Umberto
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- A click chemistry route to 2-functionalised PEGylated and cationic β-cyclodextrins: Co-formulation opportunities for siRNA delivery
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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.
- O'Mahony, Aoife M.,Ogier, Julien,Desgranges, Stephane,Cryan, John F.,Darcy, Raphael,O'Driscoll, Caitriona M.
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- Synthesis of a β-cyclodextrin derivate and its molecular recognition behavior on modified glassy carbon electrode by diazotization
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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
- Wang, Xiuhua,Fan, Hao,Zhang, Fan,Qi, Yantao,Qiu, Wenwei,Yang, Fan,Tang, Jie,He, Pingang
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- Amino acid derivatives of β-cyclodextrin
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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.
- Ashton, Peter R.,Koeniger, Rainer,Stoddart, J. Fraser,Alker, David,Harding, Valerie D.
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- Contrastive study on β-cyclodextrin polymers resulted from different cavity-modifying molecules as efficient bi-functional adsorbents
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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.
- Bai, Lan,Hu, Chunyan,Jiang, Wei,Li, Lei,Qin, Xiaomei,Song, Fei,Wang, Yuzhong,Wei, Qikun
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- Controlled orientation of cyclodextrin derivatives immobilized on gold surfaces
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Several different cyclodextrinthiol derivatives have been immobilized on gold surfaces through a chemisorption process to form films which exhibit significantly different features. Three monothiolated cyclodextrin derivatives with different spacers between the cyclodextrin cavity and the thiol group and a mixture of multithiolated cyclodextrin were synthesized and characterized. Chemisorption of these compounds onto gold surfaces gave films which were investigated by Fourier transform infrared (FTIR) spectroscopy, time-of-flight mass spectrometry, contact angle measurements, plasmon surface polariton (PSP) spectroscopy, and cyclic voltammetry. It was found that the chemical structure of each cyclodextrin derivative had a strong influence on the molecular architecture n the resulting films, and in particular on the orientation of the cyclodextrin torus. Models were developed to describe the molecular arrangement in the filmsSeveral different cyclodextrinthiol derivatives have been immobilized on gold surfaces through a chemisorption process to form films which exhibit significantly different features. Three monothiolated cyclodextrin derivatives with different spacers between the cyclodextrin cavity and the thiol group and a mixture of multithiolated cyclodextrins were synthesized and characterized. Chemisorption of these compounds onto gold surfaces gave films which were investigated by Fourier transform infrared (FTIR) spectroscopy, time-of-flight mass spectrometry, contact angle measurements, plasmon surface polariton (PSP) spectroscopy, and cyclic voltammetry. It was found that the chemical structure of each cyclodextrin derivative had a strong influence on the molecular architecture in the resulting films, and in particular on the orientation of the cyclodextrin toms. Models were developed to describe the molecular arrangement in the films.
- Nelles, Gabriele,Weisser, Michael,Back, Roberta,Wohlfart, Peter,Wenz, Gerhard,Mittler-Neher, Silvia
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- Synthesis and self-assembly of well-defined cyclodextrin-centered amphiphilic A14B7 multimiktoarm star copolymers based on poly(ε-caprolactone) and poly(acrylic acid)
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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).
- Gou, Peng-Fei,Zhu, Wei-Pu,Xu, Ning,Shen, Zhi-Quan
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- Synthesis and drug complexation studies with ss-cyclodextrins fluorinated on the primary face
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Three fluorinated β-cyclodextrin derivatives, namely 5, 9 and 12, were prepared with the hope that the fluorine reporter group may assist in direct evaluation of the complexation properties of these potential drug carriers. Two of the synthesized derivatives, the previously reported monofluoro-β-cyclodextrin 9 and the novel trifluoroethylthio-β-cyclodextrin 12, displayed reasonable aqueous solubility and thus were suitable for drug-cyclodextrin complexation studies. Preliminary NMR results (1H and 19F) on the host-guest complex formation of both of these cyclodextrin derivatives with amantidine, a therapeutic agent employed in the treatment of Influenza A infections, are also presented.
- Diakur,Zuo,Wiebe
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- MRI probes based on C6-peracetate β-cyclodextrins: Synthesis, gadolinium complexation and in vivo relaxivity studies
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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
- Biscotti, Anais,Barbot, Cécile,Nicol, Lionel,Mulder, Paul,Sappei, Célia,Roux, Marie-Hubert,Déchamps-Olivier, Isabelle,Estour, Fran?ois,Gouhier, Géraldine
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- Improved syntheses of bis(β-cyclodextrin) derivatives, new carriers for gadolinium complexes
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In the last decade a number of reports have been published on the synthesis and characterization of bridged cyclodextrin dimers (bis-CDs) connected with linkers of different lengths and structures. These dimers, having two hydrophobic cavities in close proximity, display much higher binding affinities and molecular selectivities than parent CDs, forming stable supramolecular adducts. We describe new synthetic protocols for the preparation of bis(β-CDs) bearing 2-2′, 3-3′ and 6-6′ bridges. Some of the critical steps were carried out either under high-intensity ultrasound (US) or microwave (MW) irradiation. Bis(β-CDs) containing 6-6′ ureido- and thioureido-bridges were prepared in high yields by a MW-promoted aza-Wittig reaction using polymer-bound triphenylphosphine, while those containing 2,2′ and 3,3′ bridges were prepared from mono-alkenyl β-CDs by the cross-metathesis reaction (homodimerization) in the presence of 2 nd-generation Grubbs catalyst under sonochemical conditions. By these improved protocols CD dimers could be obtained in gram amounts to prepare stable adducts of bis-CDs with contrast agents (CAs) containing gadolinium(iii) chelates. In the case of Gd(iii) chleate "G-1" the inclusion complexes were found to be 2 to 3 orders of magnitude more stable than that formed by β-CD (Kass = 4.3 × 104 M-1 vs 8.0 × 102 M-1). Relaxivity increased as well by factors of 3 and 4, viz. from 9.1 mM-1 s-1 (β-CD) to 27.7 and 35 mM-1 s-1. The Royal Society of Chemistry 2006.
- Aime, Silvio,Gianolio, Eliana,Palmisano, Giovanni,Robaldo, Bruna,Barge, Alessandro,Boffa, Luisa,Cravotto, Giancarlo
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- Heptakis(2,3-di-O-carboxymethyl)-β-cyclodextrin as a pH-sensitive host
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Acid-dissociation of heptakis(2,3-di-O-carboxymethyl)-β-cyclodextrin occurred between pD 2 and 6. At pD 2.0, 1-pyrene-sulfonate was included into the host cavity with a binding constant of 2300 ± 100 M-1, while no complexation occurred at pD > 6.0. Much sharper pH-dependency in complexation proceeded with 1-anilino-8-naphthalenesulfonate and 2-(p-methyl-anilino)-6-naphthalenesulfonate.
- Kano, Koji,Horiki, Yasuhiro,Mabuchi, Takahiro,Kitagishi, Hiroaki
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- Micelles via self-assembly of amphiphilic beta-cyclodextrin block copolymers as drug carrier for cancer therapy
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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.
- Li, Xiufang,Liu, Hui,Li, Jianbing,Deng, Zhiwei,Li, Lingjun,Liu, Junjun,Yuan, Jing,Gao,Yang, Yanjing,Zhong
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- Synthesis and self-inclusion of bipyridine-spaced cyclodextrin dimers
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The synthesis and conformational behavior of two cyclodextrin dimers containing aromatic bipyridine spacers is presented. The proton NMR spectra of these dimers in aqueous solution show a doubling of signals in the aromatic region due to complete or partial self-inclusion of the spacer. The degree and the strength of self-inclusion is dependent on the substitution pattern of the bipyridine unit. This unexpected difference in the self-inclusion behavior is revealed by 2D NOESY and circular dichroism spectra.
- Nelissen, Hubertus F. M.,Feiters, Martinus C.,Nolte, Roeland J. M.
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- Amphipathic β-cyclodextrin nanocarriers serve as intelligent delivery platform for anticancer drug
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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.
- Liu, Hui,Chen, Jian,Li, Xiufang,Deng, Zhiwei,Gao, Peiru,Li, Jianbin,Ren, Tao,Huang, Ling,Yang, Yanjing,Zhong, Shian
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- Synthesis of 2,3-O-dibenzyl-6-O-sulfobutyl-α and β cyclodextrins: new chiral surfactants for capillary electrophoresis
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Abstract Amphiphilic sodium hexakis(2,3-O-dibenzyl-6-O-sulfobutyl)cyclomaltohexaose and sodium heptakis(2,3-O-dibenzyl-6-O-sulfobutyl)cyclomaltoheptaose were synthesized in four steps. Pyrene fluorescence studies indicate micelle formation at 90 μM in water for both modified cyclodextrins (CDs). Both CDs offer potential as chiral micellar selectors for enantiomeric separations using capillary electrophoresis. Sodium heptakis(2,3-O-dibenzyl-6-O-sulfobutyl)cyclomaltoheptaose baseline resolved fluorescent cyanobenzylindole (CBI) derivatives of d/l-serine at concentrations of 50-200 μM.
- McKee, James A.,Green, Thomas K.
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p. 4451 - 4454
(2015/06/30)
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- Macrocyclic derivative and assemblies formed therefrom
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The present invention is directed to a macrocyclic derivative which is formed by modification of a macrocycle. The invention further relates to assemblies formed by the self-assembly of such macrocyclic derivatives in aqueous solvent, and includes bilayer vesicles, micelles, monolayers, nanoparticles, colloidal assemblies and surface-coated assemblies.
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Page/Page column 12-13
(2014/10/16)
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- Anion binding properties of 2,3-O-dibenzyl-α- and β-cyclodextrin derivatives
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Cyclodextrins (CDs) have been investigated as scaffolds for the construction of anion receptors. Modified α- and β-CDs (1a and 1b, respectively), where hydroxyls on C-2 and C-3 are protected by benzyl groups have been synthesized, and their anion binding
- Karube, Nobuyuki,Ito, Kazuaki
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p. 719 - 724
(2015/04/14)
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- Acetylation of secondary hydroxy groups of α- and β-cyclodextrines silyl derivatives
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The application of acetyl chloride in the combination with different solvents and bases permitted the preparation of silyl derivatives of α- and β-cyclodextrines containing a definite amount of acetyl substituents on the secondary hydroxy groups. It was found that by means of the 1H and 13C NMR spectroscopy it is possible to make an exact attribution of acetyl groups to C2 or C3 carbon atoms of carbohydrate fragments of α- and β-cyclodextrines. Desilylation with ammonium fluoride in methanol gives acetyl derivatives of cyclodextrines containing free primary hydroxy groups.
- Grachev,Edunov,Kurochkina,Levina,Nifant'ev
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experimental part
p. 322 - 329
(2011/06/27)
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- A new access to homo- and heterodimers of α-, β-, and γ-cyclodextrin by a microwave-promoted huisgen cycloaddition
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A new and efficient synthetic protocol for the preparation of α-, β- and γ-cyclodextrin (CD) homo- and heterodimers is presented. A microwave-promoted Huisgen 1,3-dipolar cycloaddition will efficiently link together monoazido and monoacetylenic CD derivatives through a 1,2,3-triazole bridge. This well-known click reaction provides a versatile method to yield 'head-to-tail' and 'tail-to-tail' CD dimers in a broad range of combinations. Such an easy access to this kind of molecular architecture may be used to fashion ad hoc tailored CD cavities such as pinching-type structures to be exploited as nanosized reactors or molecular carriers. Preliminary estimates of the relative distances and orientations of the two CD units in each kind of dimer were obtained by molecular dynamics simulations and related calculations.
- Cravotto, Giancarlo,Mendicuti, Francisco,Martina, Katia,Tagliapietra, Silvia,Robaldo, Bruna,Barge, Alessandro
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scheme or table
p. 2642 - 2646
(2009/05/07)
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- Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): Design and synthesis
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With the hope of mimicking the chemical and biological properties of natural 6-O-methyl-D-glucose-containing polysaccharides (MGPs), synthetic 6-O-methyl-D-glucose-containing polysaccharides (sMGPs) were designed and synthesized from α-, β-, and y-cyclode
- Meppen, Malte,Wang, Yonghui,Cheon, Hwan-Sung,Kishi, Yoshito
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p. 1941 - 1950
(2007/10/03)
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- Synthesis and characterisation of sulfated amphiphilic α-, β- and γ-cyclodextrins: Application to the complexation of acyclovir
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The synthesis of sulfated amphiphilic α-, β- and γ-cyclodextrins was achieved according to the standard protection-deprotection procedure. The formation of inclusion complexes between the amphiphilic α-, β- and γ-cyclodextrins and an antiviral molecule, acyclovir (ACV) was investigated by UV-visible spectroscopy (UV-Vis) and electrospray ionisation mass spectrometry (ESIMS). UV-Vis spectroscopy allowed determination of the stoichiometry and stability constants of complexes, whereas ESIMS, a soft ionisation technique, allowed the detection of the inclusion complexes. The results showed that the non-sulfated amphiphilic cyclodextrins exhibit a 1:2 stoichiometry with acyclovir, while sulfated amphiphilic cyclodextrins, except γ-cyclodextrin, exhibit a 1:1 stoichiometry indicating the loss of one interaction site. Non-covalent interactions between acyclovir and non-sulfated amphiphilic cyclodextrins appear to take place both in the cavity of the cyclodextrin and inside the hydrophobic zone generated by alkanoyl chains. In contrast, in the case of sulfated amphiphilic cyclodextrins, the interactions appear to involve only the hydrophobic region of the alkanoyl chains.
- Dubes, Alix,Degobert, Ghania,Fessi, Hatem,Parrot-Lopez, Helene
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p. 2185 - 2193
(2007/10/03)
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- Synthesis and monolayer behavior of amphiphilic per(2,3-di-O-alkyl)-α- and β-cyclodextrins and hexakis(6-deoxy-6-thio-2,3-di-O-pentyl)-α-cyclodextrin at an air-water interface
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A synthesis of amphiphilic per(2,3-di-O-alkyl)-α- and β-cyclodextrins and hexakis(6-deoxy-6-thio-2,3-di-O-pentyl)-α-cyclodextrin and their monolayer behavior on a water surface is presented. Long alkyl chains were introduced by a treatment of the per(6-O-
- Wazynska, Monika,Temeriusz, Andrzej,Chmurski, Kazimierz,Bilewicz, Renata,Jurczak, Janusz
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p. 9119 - 9123
(2007/10/03)
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- Synthesis, conformation, and binding properties of cyclodextrin homo- and heterodimers connected through their secondary sides
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The synthesis of homo- and heterocyclodextrin (CD) dimers, containing two CD moieties that are linked through their secondary sides by alipathic or 2,2'-bipyridyl spacers is described. In these dimers, the glucose units to which the spacers are linked hav
- Venema, Fokke,Nelissen, Hubertus F. M.,Berthault, Patrick,Birlirakis, Nicolaos,Rowan, Alan E.,Feiters, Martinus C.,Nolte, Roeland J. M.
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p. 2237 - 2250
(2007/10/03)
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- Regioselective alkylation of β-cyclodextrin
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Methodology for preparation of heptakis(2,6-di-O-alkyl)-β-cyclodextrins, heptakis(2-O-alkyl)-β-cyclodextrins, and heptakis(6-O-alkyl)-β-cyclodextrins in substantially purified form has been developed. Treatment of β-cyclodextrin (1) with sodium or barium
- Bansal, Paramjit S.,Francis, Craig L.,Hart, Noel K.,Henderson, Scott A.,Oakenfull, David,Robertson, Alan D.,Simpson, Gregory W.
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p. 915 - 923
(2007/10/03)
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- Selective Functionalization and Flexible Coupling of Cyclodextrins at the Secondary Hydroxyl Face
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Methods are described for the chemo- and regioselective monofunctionalization of the secondary hydroxyl face of cyclodextrins.Monofunctionalization takes place either by nucleophilic epoxide opening of mono(2A,3A-anhydro)heptakis(6-O
- Dienst, Erik van,Snellink, Bianca H. M.,Piekartz, Irma von,Gansey, Marcel H. B. Grote,Venema, Fokke,et al.
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p. 6537 - 6545
(2007/10/03)
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- Analysis of the Conformational Behaviour of Perfunctionalized β-Cyclodextrins. Part 1. Evidence for Insertion of one of the Rim Substituents into the Cyclodextrin Cavity in Organic Solvents
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Several functionalized β-cyclodextrins have been shown to exhibit conformational isomerism.The analysis of the conformational behaviour of several derivatives strongly suggests that a slow exchange occurs between C7 and C1 conformers, the C1 probably invo
- Jullien, Ludovic,Canceill, Josette,Lacombe, Liliane,Lehn, Jean-Marie
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p. 989 - 1002
(2007/10/02)
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- Synthesis of a cycloheptaose consisting of (1->4)-linked 7-amino-6,7-dideoxy-α-D-gluco-heptopyranosyl units: A new analog of cyclomaltoheptaose
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Approaches to chain extension at the C-6 positions in cyclomaltoheptaose (1) were examined with the aim of producing novel β-cyclodextrin analogs composed of heptose or hepturonic acid units.Iron carbonyl-mediated methoxycarbonylation, and nucleophilic di
- Baer, Hans H.,Shen, Yaping,Gonzalez, Francisco Santoyo,Berenguel, Antonio Vargas,Garcia, Joaquin Isac
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p. 129 - 140
(2007/10/02)
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- Selective chemical modification of cyclomalto-oligosaccharides via tert-butyldimethylsilylation
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Selective reaction of cyclomaltoheptaose and cyclomalto-octaose with tert-butylchlorodimethylsilane in N,N-dimethylformamide in the presence of inidazole gave the heptakis(6-O-tert-butyldimethylsilyl) (21) and octakis(6-O-tert-butyldimethylsilyl) (27) der
- Takeo, Kenichi,Mitoh, Hisayoshi,Uemura, Kazuhiko
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p. 203 - 222
(2007/10/02)
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