A versatile approach towards multivalent saccharide displays on magnetic nanoparticles and phospholipid vesicles. Issue 43 (11th September 2015)

• Record Type: Journal Article
• Authors: Coxon, Thomas P.; Fallows, Thomas W.; Gough, Julie E.; Webb, Simon J.
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 43(2015)
• Page Start: 10751
• Page End: 10761
• Publication Date: 2015-09-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob01591j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A simple synthetic route to lipid, resorcinol and catechol adducts of saccharides has been developed, and used to give multivalent displays on the surface of nanostructures for cell targeting. 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 D2 O at different pD values using 1 H-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.