Cyclodextrin Bilayer Vesicles

Ravoo, Bart Jan; Darcy, Raphael

doi:10.1002/1521-3773(20001201)39:23<4324::aid-anie4324>3.0.co;2-o

Cited by 211 publications

(147 citation statements)

References 22 publications

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“…The first bilayer vesicles composed of hydroxyethylated ␤-cyclodextrins ranged in size from 50 to 300 nm in water. 90 The vesicles were composed of bilayers of cyclodextrins that enclosed an aqueous interior. Recently, Ravoo's group 91 showed that a disulfide reducing agent, dithiothreitol, could break down the vesicles in water.…”

Section: Other Vesicle-forming Self-assembled Amphiphilic Systemsmentioning

confidence: 99%

Preparation of block copolymer vesicles in solution

Soo

Eisenberg

2004

J Polym Sci B Polym Phys

365

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Block copolymer vesicles can be prepared in solution from a variety of different amphiphilic systems. Polystyreneblock-poly(acrylic acid), polystyrene-block-poly(ethylene oxide), and many other block copolymer systems can produce vesicles of a wide range of sizes; those in the range of 100 -1000 nm have been explored extensively. Different factors, such as the absolute and relative block lengths, the presence of additives (ions, homopolymers, and surfactants), the water content in the solvent mixture, the nature and composition of the solvent, the temperature, and the polydispersity of the hydrophilic block, provide control over the types of vesicles produced. Their high stability, resistance to many external stimuli, and ability to package both hydrophilic and hydrophobic compounds make them excellent candidates for use in the medical, pharmaceutical, and environmental fields.

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Section: Other Vesicle-forming Self-assembled Amphiphilic Systemsmentioning

confidence: 99%

Preparation of block copolymer vesicles in solution

Soo

Eisenberg

2004

J Polym Sci B Polym Phys

365

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“…The vesicles prepared by CD inclusion complexes have gained much attention due to their importance in enthusiastic natural biomembranes, [9,10] developing new biotechniques, smart materials, etc. [11] Reports are available on substituted CD bilayer vesicles [12] and b-CD substituted by carboxymethyl and amino groups on the narrow and wider sides, respectively, [13] to form supramolecular tapes which were 50À300 nm wide and up to 20 mm in length. The self-assembly of vesicles is based on the supramolecular complexation of guest-b-CD and guest in two-head inclusion model as well as one-head inclusion model.…”

Section: Introductionmentioning

confidence: 99%

Nanochain and vesicles formed by inclusion complexation of 4,4′-diaminobenzanilide with cyclodextrins

Rajendiran

Sankaranarayanan

Saravanan

2014

Journal of Experimental Nanoscience

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The nanochain-like agglomerates and spherical nanovesicles were formed from supramolecular self-assembly of 4,4 0 -diaminonenzanilide (DABA) with a-and b-cyclodextrins. The DABA with a-CD and b-CD inclusion complex nanomaterials were prepared and characterised by transmission electron microscopy, scanning electron microscopy, FTIR, differential scanning calorimetry, 1 H NMR and powder X-ray diffraction. 1 H NMR analysis indicated that the benzamido ring of DABA was encapsulated into the cyclodextrin (CD) cavity. Absorption and fluorescence spectral studies suggested that DABA forms different types of nanomaterials in a-CD and b-CD solutions. Higher occupied molecular orbital, lower unoccupied molecular orbital, and thermodynamic parameter values confirmed DABA dye entrapped in the CD cavities.

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“…Our model system is based on the multivalent inclusion binding of a coordination complex at the surface of ␤-cyclodextrin (␤CD) host vesicles. Previously we reported the preparation of amphiphilic ␣-, ␤-, and ␥-CDs and the corresponding bilayer vesicles, which have the ability to recognize and bind guests by size-selective inclusion in the CD host cavities at the vesicle surface (41)(42)(43)(44)(45). We also recently described the multivalent interaction of the Cu(II) and Ni(II) complexes of adamantyl (Ad)-functionalized ethylenediamine (en) L to a SAM of ␤CD molecules (46).…”

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confidence: 99%

Intravesicular and intervesicular interaction by orthogonal multivalent host–guest and metal–ligand complexation

Lim

Crespo-Biel

Stuart

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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Host vesicles composed of amphiphilic ␤-cyclodextrin CD1 recognize metal-coordination complexes of the adamantyl-functionalized ethylenediamine ligand L via hydrophobic inclusion in the ␤-cyclodextrin cavities at the vesicle surface. In the case of Cu(II) and L, the resulting coordination complex was exclusively CuL2, and the interaction with the host vesicles was intravesicular, unless the concentration of metal complex and vesicles was high (>0.1 mM). In the case of Ni(II) and L, a mixture was formed consisting of mainly NiL and NiL2, the interaction with the host vesicles was effectively intervesicular, and addition of the guest-metal complex resulted in aggregation of the vesicles into dense, multilamellar clusters even in dilute solution [1 M Ni(II)]. The metal-L complex could be eliminated by a strong chelator such as EDTA, and the intervesicular interaction could be suppressed by a competitor such as unmodified ␤-cyclodextrin. The result from this investigation is that the strongest metal-coordination complex [Cu(II) with L] binds exclusively intravesicularly, whereas the weakest metal-coordination complex [Ni(II) with L] binds predominantly intervesicularly and is the strongest interfacial binder. These experimental observations are confirmed by a thermodynamic model that describes multivalent orthogonal interactions at interfaces.self-assembly ͉ vesicles ͉ cyclodextrins M ultivalent, noncovalent interactions at the interface of cell membranes are involved in a variety of biological processes such as cell-cell signaling, pathogen identification, and inflammatory response (1). Multivalent binding events have collective properties that are qualitatively and quantitatively different from the contributing monovalent interactions. For example, multivalent interactions lead to higher binding affinities and can afford larger contact areas between surfaces (1-3). Multivalency can be conveniently described by an effective concentration (C eff ) term that represents a probability of interaction between two interlinked reactive or complementary entities and symbolizes the concentration of one of the reacting or interacting functionalities as experienced by its counterpart (4, 5). Versatile model systems to investigate multivalent noncovalent interactions at the dynamic interface between cell membranes and the surrounding aqueous solution include self-assembled monolayers (SAMs) (6-11), nanoparticles (12-14), solid-supported lipid bilayers (15, 16), and bilayer vesicles (17-19).Metal-ligand coordination has been exploited to generate complex molecular architectures with specific topology, high stability, and original properties in aqueous solution (16,20,21). The N-nitrilotriacetic acid-histidine interaction is particularly interesting in a biological context. N-nitrilotriacetic acidfunctionalized lipids (22, 23) and SAMs (24, 25) have been used to immobilize proteins through multivalent interactions. In a comparable approach, the multivalent binding of Cu(II) ions to a membrane-bound dansyl-ethylenediamine conjugat...

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Cyclodextrin Bilayer Vesicles

Cited by 211 publications

References 22 publications

Preparation of block copolymer vesicles in solution

Preparation of block copolymer vesicles in solution

Nanochain and vesicles formed by inclusion complexation of 4,4′-diaminobenzanilide with cyclodextrins

Intravesicular and intervesicular interaction by orthogonal multivalent host–guest and metal–ligand complexation

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