Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK.
School of Materials, University of Manchester, MSS Tower, M13 9PL, Manchester, UK.
Org Biomol Chem. 2015 Nov 21;13(43):10751-61. doi: 10.1039/c5ob01591j.
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 (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.
已经设计出一种简单的合成路线，用于生产可以在磁铁矿纳米颗粒和磷脂囊泡表面上提供糖多价显示的涂层剂。一种多功能且潜在高通量的缩合反应允许快速合成各种具有脂质、间苯二酚或儿茶酚末端的糖基酰肼缀合物，每种产物的产率和α-构型纯度都很高。使用（1）H-NMR 光谱法在不同的 pD 值下评估了这些加合物的水解稳定性，而石英晶体微天平耗散监测（QCM-D）证实双层和纳米颗粒上的糖功能仍然可被凝集素识别。这些多价糖显示促进了纳米颗粒与细胞的相互作用，例如，与未涂层的纳米颗粒相比，N-乙酰葡萄糖胺涂层的纳米颗粒与 3T3 成纤维细胞的相互作用更加有效。尽管可能对氧化敏感，但与间苯二酚涂层相比，磁铁矿纳米颗粒上的儿茶酚涂层被发现更稳定，并与成纤维细胞产生更好的纳米颗粒相互作用。
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