Abstract
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.
Highlights
Cyclodextrins (CDs) are cyclic oligosaccharides with unique inside/outside distribution of hydrophobic/hydrophilic areas, resulting in well-defined topological amphiphilicity
The academic andtechnological interest for cyclodextrins has been historically dominated by their inclusion complex-formation ability, which has translated into numerous applications in fields like food [1,2], cosmetics [3], environment [4,5], and medicine [3,6,7,8,9,10]
They encountered that the self-assembling and transfection aptitude of these compounds were very sensitive to the aminoglycoside structure: 6-amino-6-deoxy and 2-amino-2-deoxy-β-D-glucopyranosylthioureido conjugates readily formed glycoCDplexes (75–100 nm hydrodynamic diameter) in the presence of plasmid DNA (pDNA), but only the first ones were efficient at promoting transfection in COS-7 cells
Summary
Cyclodextrins (CDs) are cyclic oligosaccharides with unique inside/outside distribution of hydrophobic/hydrophilic areas, resulting in well-defined topological amphiphilicity. They encountered that the self-assembling and transfection aptitude of these compounds were very sensitive to the aminoglycoside structure: 6-amino-6-deoxy and 2-amino-2-deoxy-β-D-glucopyranosylthioureido conjugates readily formed glycoCDplexes (75–100 nm hydrodynamic diameter) in the presence of pDNA, but only the first ones were efficient at promoting transfection in COS-7 cells. The 6-amino-6-deoxyglucoside pGaCD was found to selectively bind the galactose-specific lectin peanut agglutinine (PNA) and preferentially internalize BNL-CL2 hepatocytes by ASGPR-mediated endocytosis [171], highlighting this iminosugar as a dual nucleic acid/lectin receptor binder when presented in multivalent form (Figure 17). Examples on record include host–guest mannose- and galactose-modified quantum dots (glyco-QDs) for the optical detection of carbohydrate–protein interactions [191,192] and mannose-decorated mesoporous silica-coated gold nanorods [193] and graphene shits [194] for E. coli bacteria agglutination and killing
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