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Issue 43, 2015
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A versatile approach towards multivalent saccharide displays on magnetic nanoparticles and phospholipid vesicles

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Abstract

A simple synthetic route has been devised for the production of coating agents that can give multivalent displays of saccharides on the surface of magnetite nanoparticles and phospholipid vesicles. A versatile and potentially high-throughput condensation reaction allowed the rapid synthesis of a variety of glycosylhydrazide conjugates with lipid, resorcinol or catechol termini, each in good yield and high anomeric purity. The hydrolytic stability of these adducts was assessed in D2O at different pD values using 1H-NMR spectroscopy, whilst quartz crystal microbalance with dissipation monitoring (QCM-D) confirmed that the saccharide functionality on bilayers and on nanoparticles was still available to lectins. These multivalent saccharide displays promoted nanoparticle interactions with cells, for example N-acetylglucosamine-coated nanoparticles interacted much more effectively with 3T3 fibroblasts than uncoated nanoparticles with these cells. Despite potential sensitivity to oxidation, catechol coatings on magnetite nanoparticles were found to be more stable and generate better nanoparticle interactions with fibroblasts than resorcinol coatings.

Graphical abstract: A versatile approach towards multivalent saccharide displays on magnetic nanoparticles and phospholipid vesicles

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The article was received on 30 Jul 2015, accepted on 01 Sep 2015 and first published on 01 Sep 2015


Article type: Paper
DOI: 10.1039/C5OB01591J
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Citation: Org. Biomol. Chem., 2015,13, 10751-10761
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    A versatile approach towards multivalent saccharide displays on magnetic nanoparticles and phospholipid vesicles

    T. P. Coxon, T. W. Fallows, J. E. Gough and S. J. Webb, Org. Biomol. Chem., 2015, 13, 10751
    DOI: 10.1039/C5OB01591J

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