Cyclodextrin-Based Functional Glyconanomaterials

Rivero-Barbarroja, Gonzalo; Benito, Juan M.; Fernández, José Manuel Garcı́a

doi:10.3390/nano10122517

Cited by 22 publications

(12 citation statements)

References 217 publications

(280 reference statements)

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“…An exhaustive review on amphiphilic β-cyclodextrins harboring arborescent architectures have been described by the group of García Fernández et al [ 58 ]. Moreover, analogous constructs were recently described using doxorubicin-loaded (Dox) glycodendrimersomes armed with mannopyranoside dendrons that are used as targeting components.…”

Section: Arborescent Neoglycolipids Built From Cyclic Scaffoldsmentioning

confidence: 99%

Recent Development in the Design of Neoglycoliposomes Bearing Arborescent Architectures

2021

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This brief review highlights systematic progress in the design of synthetic glycolipid (neoglycolipids) analogs evolving from the conventional architectures of natural glycosphingolipids and gangliosides. Given that naturally occurring glycolipids are composed of only one hydrophilic sugar head-group and two hydrophobic lipid tails embedded in the lipid bilayers of the cell membranes, they usually require extraneous lipids (phosphatidylcholine, cholesterol) to confer their stability. In order to obviate the necessity for these additional stabilizing ingredients, recent investigations have merged dendrimer chemistry with that of neoglycolipid syntheses. This singular approach has provided novel glycoarchitectures allowing reconsidering the necessity for the traditional one to two hydrophilic/hydrophobic ratio. An emphasis has been provided in the recent design of modular arborescent neoglycolipid syntheses coined glycodendrimersomes.

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Section: Arborescent Neoglycolipids Built From Cyclic Scaffoldsmentioning

confidence: 99%

Recent Development in the Design of Neoglycoliposomes Bearing Arborescent Architectures

2021

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“…To obtain modified cyclodextrins, two main strategies are available: the first is a regioselective synthesis leading to pure and well-defined cyclodextrin derivatives. Many examples are reported, such as hetero-difunctionalised β-cyclodextrin derivatives [ 6 ] or cyclodextrin-based functional glyconanomaterials [ 7 ]. Recently, we have proposed an optimised and convergent chemical synthesis of lipophosphoramidyl permethylated βCDs (Lipidyl-βCDs) with various chain lengths [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Mass Spectrometry, Ion Mobility Separation and Molecular Modelling: A Powerful Combination for the Structural Characterisation of Substituted Cyclodextrins Mixtures

Rigaud

Dosso

Lesur

et al. 2022

IJMS

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When working on the synthesis of substituted cyclodextrins (CDs), the main challenge remains the analysis of the reaction media content. Our objective in this study was to fully characterise a complex isomers mixture of Lipidyl-βCDs (LipβCD) obtained with a degree of substitution 1 (DS = 1) from a one-step synthesis pathway. The benefit of tandem mass spectrometry (MS/MS) and ion mobility separation hyphenated with mass spectrometry (IM-MS) was investigated. The MS/MS fragment ion‘s relative intensities were analysed by principal component analysis (PCA) to discriminate isomers. The arrival time distribution (ATD) of each isomer was recorded using a travelling wave ion mobility (TWIM) cell allowing the determination of their respective experimental collision cross section (CCSexp). The comparison with the predicted theoretical CCS (CCSth) obtained from theoretical calculations propose a regioisomer assignment according to the βCD hydroxyl position (2, 3, or 6) involved in the reaction. These results were validated by extensive NMR structural analyses of pure isomers combined with molecular dynamics simulations. This innovative approach seems to be a promising tool to elucidate complex isomer mixtures such as substituted cyclodextrin derivatives.

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“…Examples of the use of β-CDs bound by thiourea linkers can be found in the recent review about CD based functional glyconomaterials [ 235 ].…”

Section: Introductionmentioning

confidence: 99%

Mono-6-Substituted Cyclodextrins—Synthesis and Applications

Kasal

Jindřich

2021

Molecules

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Cyclodextrins are well known supramolecular hosts used in a wide range of applications. Monosubstitution of native cyclodextrins in the position C-6 of a glucose unit represents the simplest method how to achieve covalent binding of a well-defined host unit into the more complicated systems. These derivatives are relatively easy to prepare; that is why the number of publications describing their preparations exceeds 1400, and the reported synthetic methods are often very similar. Nevertheless, it might be very demanding to decide which of the published methods is the best one for the intended purpose. In the review, we aim to present only the most useful and well-described methods for preparing different types of mono-6-substituted derivatives. We also discuss the common problems encountered during their syntheses and suggest their optimal solutions.

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Cyclodextrin-Based Functional Glyconanomaterials

Cited by 22 publications

References 217 publications

Recent Development in the Design of Neoglycoliposomes Bearing Arborescent Architectures

Recent Development in the Design of Neoglycoliposomes Bearing Arborescent Architectures

Mass Spectrometry, Ion Mobility Separation and Molecular Modelling: A Powerful Combination for the Structural Characterisation of Substituted Cyclodextrins Mixtures

Mono-6-Substituted Cyclodextrins—Synthesis and Applications

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