Influenza-binding sialylated polymer coated gold nanoparticles prepared via RAFT polymerization and reductive amination

Abstract

We report on a straightforward strategy to fabricate bioactive glycosylated gold nanoparticles via a combination of RAFT polymerization, carbohydrate ligation through reductive amination and thiol-gold self-assembly. This approach is used for the design of gold nanoparticles decorated with the complex sialylated glycan Neu5Ac-α-2-6-Gal, and we demonstrate multivalent and specific recognition between the nanoparticles, lectins and hemagglutinin on the surface of the influenza virus.

A Synthetic, Transiently Thermoresponsive Homopolymer with UCST Behaviour within a Physiologically Relevant Window

“…In this study, we chose poly( N ‐(2‐hydroxypropyl)methacrylamide) (poly(HPMA)) as a polymeric scaffold owing to its biocompatibility and non‐immunogenic nature, and modified the hydroxy groups with glycolamide through a degradable carbonate ester linkage. We reasoned that the resulting carbonate ester bond would contribute to both increased hydrophobicity and hydrogen bond formation, whereas the pending primary amide bond would be available for hydrogen bonding.…”

“…In this study,w ec hose poly(N-(2-hydroxypropyl)methacrylamide) (poly(HPMA)) as ap olymeric scaffold owing to its biocompatibility and non-immunogenic nature, [29][30][31][32] and modified the hydroxy groups with glycolamide through ad egradable carbonate ester linkage.W er easoned that the resulting carbonate ester bond would contribute to both increased hydrophobicity and hydrogen bond formation, whereas the pending primary amide bond would be available for hydrogen bonding.Importantly,hydrolysis of the carbonate ester linkage should result in unmodified poly(HPMA) and loss of the responsive behaviour,t hat is,w ater solubility (Scheme 1A). Them onomer synthesis is depicted in Scheme 1B,and is based on the utilization of our recently reported strategy for the hydrophobic modification of HPMA.…”

Sialyl‐LacNAc‐PNA⋅DNA Concatamers by Rolling‐Circle Amplification as Multivalent Inhibitors of Influenza A Virus Particles

“…This has motivated the development of multivalent scaffolds that present multiple copies of HA ligands. Polymers, dendrimers, and nanoparticles have all been decorated with carbohydrate‐based HA binders. In a notable example, Whitesides et al .…”

Synthetisch hergestellte, transient thermoresponsive Homopolymere mit einer oberen kritischen Lösungstemperatur für physiologisch relevante Anwendungen

“…In dieser Studie haben wir uns deshalb für Poly( N ‐(2‐hydroxypropyl)methacrylamid) (Poly(HPMA)) als polymeren Träger entschieden, da er eine hohe Biokompatibilität und nur geringe Immunogenität aufweist . Dabei lassen sich seine Hydroxylgruppen über abbaubare Carbonateinheiten mit Glycolsäureamid derivatisieren.…”

“…In dieser Studie haben wir uns deshalb fürP oly(N-(2-hydroxypropyl)methacrylamid) (Poly(HPMA)) als polymeren Tr äger entschieden, da er eine hohe Biokompatibilitätu nd nur geringe Immunogenitäta ufweist. [29][30][31][32] [33] Dabei wird in einer ersten Stufe HPMA mit 1,1'-Carbonyldiimidazol (CDI) aktiviert und nach Aufreinigung mit Glycolsäureamid umgesetzt. Nach sorgfältiger säulenchromatographischer Auftrennung an Silikagel konnte so das Produkt HPMA-GA (zu beachten, GA steht hier fürG lycolsäureamid) erfolgreich isoliert und mittels 1 H-, 13 C-, COSY-, HSQC-NMR und ESI-Massenspektrometrie nachgewiesen werden (Abbildung S1-S5 in den Hintergrundinformationen).…”