Monovalent maleimide functionalization of gold nanoparticles via copper-free click chemistry.

D J Nieves,R Lévy,N S Azmi,E A Yates,R Xu,D G Fernig

doi:10.1039/c4cc05909c

Abstract

A single maleimide was installed onto the self-assembled monolayer of gold nanoparticles by copper-free click chemistry. Simple covalent biofunctionalisation is demonstrated by coupling fibroblast growth factor 2 and an oligosaccharide in a 1 : 1 stoichiometry by thiol-Michael addition.

Highlights

A single maleimide was installed onto the self-assembled monolayer of gold nanoparticles by copper-free click chemistry
Simple covalent biofunctionalisation is demonstrated by coupling fibroblast growth factor 2 and an oligosaccharide in a 1 : 1 stoichiometry by thiol-Michael addition
Gold nanoparticles have been used in biology for several decades as a contrast agent in immunoelectron microscopy

Summary

Introduction

A single maleimide was installed onto the self-assembled monolayer of gold nanoparticles by copper-free click chemistry. The N3NPs were used for a copper-free click reaction with 20 mM of maleimide functionalised cyclooctyne (DIBO-Mal) for one hour in the dark with mixing on a rotating wheel to yield maleimide functionalised gold nanoparticles (Fig. S3, ESI†). After removal of excess DIBO-Mal by Sephadex G-25 size-exclusion chromatography with TBST0.05% as the mobile phase, the resulting nanoparticles (DIBO-Mal NPs) were used for Michael addition reactions with molecules bearing thiol groups.

Results

Conclusion