118646-79-0Relevant academic research and scientific papers
Erythrocyte-like liposomes prepared by means of amphiphilic cyclodextrin sulfates
Sukegawa, Takeshi,Furuike, Tetsuya,Niikura, Kenichi,Yamagishi, Akihiko,Monde, Kenji,Nishimura, Shin-Ichiro
, p. 430 - 431 (2002)
A novel class of sulfated glycolipids with excellent self-assembling capacity to form stable monolayers at an air-water interface and specific erythrocyte-like liposomes was synthesised from α, β, and γ-cyclodextrins as starting materials.
A new access to homo- and heterodimers of α-, β-, and γ-cyclodextrin by a microwave-promoted huisgen cycloaddition
Cravotto, Giancarlo,Mendicuti, Francisco,Martina, Katia,Tagliapietra, Silvia,Robaldo, Bruna,Barge, Alessandro
, p. 2642 - 2646 (2008)
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.
The 2,3-anhydro-α-cyclomannin-1-propanol hexahydrate: Topography, lipophilicity pattern and solid-state architecture
Immel, Stefan,Lichtenthaler, Frieder W.,Lindner, Hans J.,Fujita, Kahee,Fukudome, Makato,Nogami, Yasuyoshi
, p. 27 - 36 (2000)
As evidenced by its X-ray structural analysis, 2,3-anhydro-α-cyclomannin 6, a cyclooligosaccharide consisting of six α-(1→4)-linked 2,3-anhydro-D-mannopyranose units, readily incorporates 1-propanol into its cavity such that hydrophobic and hydrophilic surface regions of guest and host match at their interfaces. Together with water, the macrocycle and its guest assemble into a unique solid-state architecture, featuring layers of head-to-head dimers of the macrocycle with its guest, separated by equally distinct layers of water molecules, which are engaged in an intense hydrogen bonding network with the 6-CH2OH and the propanol-OH groups. The overall guest-host topography is thus reverse to that of the respective ethanol inclusion complex.1 Copyright (C) 2000 Elsevier Science Ltd.
Synthesis and characterisation of sulfated amphiphilic α-, β- and γ-cyclodextrins: Application to the complexation of acyclovir
Dubes, Alix,Degobert, Ghania,Fessi, Hatem,Parrot-Lopez, Helene
, p. 2185 - 2193 (2003)
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.
New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands
Aime, Silvio,Gianolio, Eliana,Arena, Francesca,Barge, Alessandro,Martina, Katia,Heropoulos, George,Cravotto, Giancarlo
, p. 370 - 379 (2009)
Bridged cyclodextrin dimers and trimers, in which respectively two and three hydrophobic cavities lie in close proximity, display much higher binding affinities and molecular selectivities than do parent cyclodextrins (CDs). By joining βCD units with links inserted at different positions (2-2′, 3-2′, 6-2′ or 6-2′-6″) and interposing spacers of different lengths and shapes, multicavity structures can be synthesized that are precisely tailored to fit specific guest molecules. This enzyme-mimicking strategy can also be used to generate stable supramolecular adducts. A series of CD dimers and trimers was prepared in good yields by carrying out the critical synthetic steps under power ultrasound (US) or microwave (MW) irradiation. Starting from azide and acetylenic CD derivatives, we exploited an efficient MW-promoted Huisgen 1,3-dipolar cycloaddition in the presence of Cu(I) salts. The resulting bridged CD derivatives gave stable adducts with magnetic-resonance-imaging contrast agents (MRI CAs) containing gadolinium(III) chelates. These inclusion complexes were found to be 2 to 3 orders of magnitude more stable than those formed by βCD and to be endowed with high relaxivity values.
A Complex Comprising a Cyanine Dye Rotaxane and a Porphyrin Nanoring as a Model Light-Harvesting System
Anderson, Harry L.,Caycedo-Soler, Felipe,Frawley, Andrew T.,Huelga, Susana F.,Kendrick, William J.,Mattioni, Andrea,Plenio, Martin B.,Pruchyathamkorn, Jiratheep
, p. 16455 - 16458 (2020)
A nanoring-rotaxane supramolecular assembly with a Cy7 cyanine dye (hexamethylindotricarbocyanine) threaded along the axis of the nanoring was synthesized as a model for the energy transfer between the light-harvesting complex LH1 and the reaction center
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
Wazynska, Monika,Temeriusz, Andrzej,Chmurski, Kazimierz,Bilewicz, Renata,Jurczak, Janusz
, p. 9119 - 9123 (2000)
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-
Synthesis of 2,3-O-dibenzyl-6-O-sulfobutyl-α and β cyclodextrins: new chiral surfactants for capillary electrophoresis
McKee, James A.,Green, Thomas K.
, p. 4451 - 4454 (2015)
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.
Anion binding properties of 2,3-O-dibenzyl-α- and β-cyclodextrin derivatives
Karube, Nobuyuki,Ito, Kazuaki
, p. 719 - 724 (2015/04/14)
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
Acetylation of secondary hydroxy groups of α- and β-cyclodextrines silyl derivatives
Grachev,Edunov,Kurochkina,Levina,Nifant'ev
experimental part, p. 322 - 329 (2011/06/27)
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.
