Heterogeneous-phase Sonogashira cross-coupling reaction on COC surface for the grafting of biomolecules – Application to isatin

Cécile Soulignac (1) , Benedetta Cornelio (1) , Frédérique Brégier (1) , Franck Le Derf (1) , Jean-François Brière (1) , Thomas Clamens (2) , Olivier Lesouhaitier (2) , François Estour (1) , Julien Vieillard (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 LMSM - Laboratoire de Microbiologie Signaux et Microenvironnement

The grafting of 5-iodoisatin heterocycle on a cyclic olefin copolymer (COC) and a gold surface was performed using a heterogeneous phase Sonogashira reaction consisting of coupling 5-iodoisatin with an arylalkyne previously introduced onto the surfaces. This optimized strategy takes advantage of the well-established methodology to functionalize COC or gold surfaces using aryldiazonium surface chemistry. Herein, we reported the first example of an isatin decorated polymeric or metallic surface. The surfaces were analyzed with a combination of techniques such as IR (Infrared spectroscopy), XPS (X-Ray photoelectron spectroscopy) and SPR (surface plasmon resonance). Docking studies showed that isatin and two derivatives interact with AmiC, a dimeric protein produced by Pseudomonas aeruginosa. Bacterial adhesion on isatin−COC platform was also observed. This general strategy for robust surface functionalization represents an easy approach for patterning surfaces with compounds of biological interest, allowing access to a large panel of original biosensors.

Domains: Chemical Sciences

Cécile Soulignac, Benedetta Cornelio, Frédérique Brégier, Franck Le Derf, Jean-François Brière, et al.. Heterogeneous-phase Sonogashira cross-coupling reaction on COC surface for the grafting of biomolecules – Application to isatin. Colloids and Surfaces B: Biointerfaces, 2019, 181, pp.639-647. ⟨10.1016/j.colsurfb.2019.06.001⟩. ⟨hal-02197292⟩