A practical synthesis of amphiphilic cyclodextrins fully substituted with sugar residues on the primary face

Sallas, Florence; Niikura, Kenichi; Nishimura, Shin‐Ichiro

doi:10.1039/b316365b

Cited by 23 publications

(9 citation statements)

References 14 publications

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“…The groups of Darcy and Mazzaglia developed a novel prototype of GaCDs in which the hydrophobic tails are installed Scheme 37 Synthesis of multivalent liposomes from glycoamphiphilic cyclodextrins. 135 at the primary face of the bCD platform and the glycosyl residues at the secondary rim, a ''jellyfish-type'' arrangement. 137 The synthetic approach benefits from the wellestablished efficiency of the nucleophilic displacement of (C-6)-bromo groups by thiolate to introduce alkylthio chains of different length, followed by etherification of the more acidic OH-2 groups with ethylene carbonate.…”

Section: Self-assembled Glycocoated Liposomes Micelles and Vesicles mentioning

confidence: 99%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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Section: Self-assembled Glycocoated Liposomes Micelles and Vesicles mentioning

confidence: 99%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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“…The interest of such systems for targeted drug delivery is obvious. Early work in the field was conducted by the groups of Nishimura, Darcy and Mazzaglia [ 50 , 51 , 52 , 53 , 54 ] and has already been reviewed [ 23 ]. Recent contributions by Seeberger, Yin and coworkers focus on the optimization of amphiphilic mannosylated βCD derivatives in terms of self-assembling properties and stability of the resulting mannose-functionalized nanoparticles [ 55 ].…”

Section: Amphiphilicity As An Action Principle For Glycocd Self-asmentioning

confidence: 99%

Cyclodextrin-Based Functional Glyconanomaterials

2020

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Cyclodextrins (CDs) have long occupied a prominent position in most pharmaceutical laboratories as “off-the-shelve” tools to manipulate the pharmacokinetics of a broad range of active principles, due to their unique combination of biocompatibility and inclusion abilities. The development of precision chemical methods for their selective functionalization, in combination with “click” multiconjugation procedures, have further leveraged the nanoscaffold nature of these oligosaccharides, creating a direct link between the glyco and the nano worlds. CDs have greatly contributed to understand and exploit the interactions between multivalent glycodisplays and carbohydrate-binding proteins (lectins) and to improve the drug-loading and functional properties of nanomaterials through host–guest strategies. The whole range of capabilities can be enabled through self-assembly, template-assisted assembly or covalent connection of CD/glycan building blocks. This review discusses the advancements made in this field during the last decade and the amazing variety of functional glyconanomaterials empowered by the versatility of the CD component.

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“…Sallas et al42 prepared CDs esterified on the secondary side and glycosylated on the primary side ( 52 , 55 ). Glycosylation involved reaction with a glucosamine having either a terminal amino group or an active ester group (Scheme ).…”

Section: Synthesis Of Amphiphilic Cyclodextrinsmentioning

confidence: 99%

Amphiphilic Cyclodextrins – Advances in Synthesis and Supramolecular Chemistry

2008

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Amphiphilic cyclodextrins represent a new generation of these oligosaccharides, which are well known previously as host molecules in water. Cyclodextrins are now being modified with polar groups, lipophilic groups and conjugates which elaborate further their amphiphilicity and molecular recognition. The resulting amphiphiles are host molecules capable of forming all the assemblies expected of amphiphiles, but showing additional supramolecular properties. Examples of these macrocyclic amphiphiles are by now known that form thermotropic liquid crystals, while lyotropic assemblies include micelles, unimolecular micelles, nanoparticles, monolayers and bilayer vesicles. The assembly proper- Cyclodextrin Amphiphiles: A New Generation of CyclodextrinsCyclodextrins (CDs) are macrocyclic oligosaccharides composed of -(+)-glucopyranosyl units linked α(1Ǟ4).[a] Centre for Synthesis and Chemical Biology of the UCD Con-

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A practical synthesis of amphiphilic cyclodextrins fully substituted with sugar residues on the primary face

Abstract: New amphiphilic cyclodextrins fully substituted with sugar residues on the primary face have been synthesised and enzymatically modified.

Cited by 23 publications

References 14 publications

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Cyclodextrin-Based Functional Glyconanomaterials

Amphiphilic Cyclodextrins – Advances in Synthesis and Supramolecular Chemistry

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