A versatile approach for the immobilization of amines via copper-free “click” reaction between azido self-assembled monolayer and alkynyl Fischer carbene complex. Application to the detection of staphylococcal enterotoxin A antibody

A copper-free “click” reaction between an azido-terminated self-assembled monolayer (SAM) chemisorbed on planar gold-coated glass sensors and an alkynyl Fischer carbene complex yielded functionalized surfaces onto which facile and swift grafting of amine-containing molecules was achieved via aminolysis of the Fischer carbene moieties. The course of this process was conveniently monitored by Polarization-Modulation Infrared Reflection-Absorption Spectroscopy (PM-IRRAS), contact angle measurements and X-ray photoelectron spectroscopy (XPS). A study of the parameters involved in the covalent grafting of the model protein bovine serum albumin (BSA) to the Fischer carbene modified SAM was carried out. As an application, the bacterial toxin staphylococcal enterotoxin A (SEA) produced by some pathogenic strains of Staphylococcus aureus was immobilized on the gold chips and immunocapture of a polyclonal antibody raised against SEA was detected by PM-IRRAS so as to ultimately construct an optical immunosensor for the detection of this toxin in food samples.

Graphical abstractA copper-free “click” reaction between an azido-terminated self-assembled monolayer (SAM) chemisorbed on planar gold-coated glass sensors and an alkynyl Fischer carbene complex yielded functionalized surfaces onto which facile and swift grafting of amine-containing molecules was achieved via aminolysis of the Fischer carbene moieties.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights►“Click” reaction as a means of activation of azido-terminated SAM on gold. ► Staphylococcal enterotoxin A immobilization by Fischer carbene aminolysis. ► Antibody recognition by mid-IR optical transduction.