Influence of chemical structure of amphiphilic β-cyclodextrins on their ability to form stable nanoparticles

Gèze, Annabelle; Aous, Soad; Baussanne, Isabelle; Putaux, Jean‐Luc; Defaye, J.; Wouessidjewe, Denis

doi:10.1016/s0378-5173(02)00192-8

Cited by 40 publications

(10 citation statements)

References 4 publications

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“…The amount of partially acylated species in β-CDsa was also found to play an important role in regulating the mean diameter size and suspension stability of nanospheres. 228 Amphiphilic β-CD (β-CDa) derivatives, 6-N-CAPRO-β-CD and β-CDC6 with 6C aliphatic chains on the primary and secondary face respectively, enhanced the solubility and therapeutic efficacy of model drugs, bifonazole and clotrimazole. The β-CDa derivatives formed inclusion complexes with the drugs and with the nanoprecipitation technique the derivatives gave nanospheres of less than 300 nm with no use of surfactants.…”

Section: Nanoparticlesmentioning

confidence: 99%

Cyclodextrins in drug delivery: An updated review

et al. 2005

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The purpose of this review is to discuss and summarize some of the interesting findings and applications of cyclodextrins (CDs) and their derivatives in different areas of drug delivery, particularly in protein and peptide drug delivery and gene delivery. The article highlights important CD applications in the design of various novel delivery systems like liposomes, microspheres, microcapsules, and nanoparticles. In addition to their well-known effects on drug solubility and dissolution, bioavailability, safety, and stability, their use as excipients in drug formulation are also discussed in this article. The article also focuses on various factors influencing inclusion complex formation because an understanding of the same is necessary for proper handling of these versatile materials. Some important considerations in selecting CDs in drug formulation such as their commercial availability, regulatory status, and patent status are also summarized. CDs, because of their continuing ability to find several novel applications in drug delivery, are expected to solve many problems associated with the delivery of different novel drugs through different delivery routes.

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Section: Nanoparticlesmentioning

confidence: 99%

Cyclodextrins in drug delivery: An updated review

et al. 2005

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“…Supramolecular properties of the prepared derivatives were studied by a set of methods allowing characterization of supramolecular behavior at various levels – from binary complexation, over supramolecular oligomers to large assemblies; namely by isothermal titration calorimetry (ITC) [ 16 ], 1 H nuclear magnetic resonance spectroscopy ( 1 H NMR), dynamic light scattering (DLS) [ 18 – 21 ] and cryo-transmission electron microscopy (Cryo-TEM) [ 22 – 24 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

Blahová

Filippov

Kováčik

et al. 2017

Beilstein J. Org. Chem.

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Monosubstituted derivatives of γ-cyclodextrin (γ-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted γ-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of γ-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of γ-CD and 2-vinylnaphthalene which gives yields of about 16–25% (2–5% starting from γ-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of γ-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12–19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM.

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“…The chemical structures in (b), (d), (e), and (f) depict the compounds studied in refs. [ 12 , 23 , 41 , 42 ] respectively. ( a ) Reprinted with permission from [ 39 ].…”

Section: Amphiphilic Cyclodextrinsmentioning

confidence: 99%

“…Grafting of hydrophobic moieties on the primary or the secondary faces of natural cyclodextrins (cyclic oligosaccharides forming nanocavity structures) confers them an amphiphilic character [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. Synthesis of various modified cyclodextrins has been undertaken because such amphiphilic compounds may self-organize in aqueous phase to form supramolecular assemblies as drug carriers of high stability upon dilution [ 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. The combination between the ability of the cyclodextrin derivatives to form colloidal suspensions of nano-sized dispersed particles and their capacity to form inclusion complexes with hydrophobic drugs has distinguished these systems as pretty valuable for drug encapsulation [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

Nano-Assemblies of Modified Cyclodextrins and Their Complexes with Guest Molecules: Incorporation in Nanostructured Membranes and Amphiphile Nanoarchitectonics Design

2014

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A variety of cyclodextrin-based molecular structures, with substitutions of either primary or secondary faces of the natural oligosaccharide macrocycles of α-, β-, or γ-cyclodextrins, have been designed towards innovative applications of self-assembled cyclodextrin nanomaterials. Amphiphilic cyclodextrins have been obtained by chemical or enzymatic modifications of their macrocycles using phospholipidyl, peptidolipidyl, cholesteryl, and oligo(ethylene oxide) anchors as well as variable numbers of grafted hydrophobic hydrocarbon or fluorinated chains. These novel compounds may self-assemble in an aqueous medium into different types of supramolecular nanoassemblies (vesicles, micelles, nanorods, nanospheres, and other kinds of nanoparticles and liquid crystalline structures). This review discusses the supramolecular nanoarchitectures, which can be formed by amphiphilic cyclodextrin derivatives in mixtures with other molecules (phospholipids, surfactants, and olygonucleotides). Biomedical applications are foreseen for nanoencapsulation of drug molecules in the hydrophobic interchain volumes and nanocavities of the amphiphilic cyclodextrins (serving as drug carriers or pharmaceutical excipients), anticancer phototherapy, gene delivery, as well as for protection of instable active ingredients through inclusion complexation in nanostructured media.

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Influence of chemical structure of amphiphilic β-cyclodextrins on their ability to form stable nanoparticles

Cited by 40 publications

References 4 publications

Cyclodextrins in drug delivery: An updated review

Cyclodextrins in drug delivery: An updated review

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

Nano-Assemblies of Modified Cyclodextrins and Their Complexes with Guest Molecules: Incorporation in Nanostructured Membranes and Amphiphile Nanoarchitectonics Design

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