Introduction of anti-fouling coatings at the surface of supramolecular elastomeric materials via post-modification of reactive supramolecular additives

Abstract

Protein repellent coatings have been extensively studied to introduce anti-fouling properties at material surfaces. Here we introduce a covalent anti-fouling coating at the surface of supramolecular ureidopyrimidinone (UPy) based materials introduced via post-modification of reactive UPy-functionalized tetrazine additives incorporated into the supramolecular polymer material. After material formulation, an anti-fouling coating comprised of bicyclononyne (BCN) functionalized poly(ethylene glycol) (PEG) polymers was reacted. This coating was covalently attached to the surface via a highly selective electron-demand Diels–Alder cycloaddition between tetrazine and BCN. The anti-fouling properties of three different BCN-PEG polymers, mono-functional-PEG-BCN, bi-functional-PEG-BCN and star-PEG-BCN, respectively, were systematically studied. The mono-functional-PEG-BCN showed minor reduction in both protein adsorption and cell adhesion, whereas the bi-functional-PEG-BCN and the star-PEG-BCN polymer coating demonstrated complete anti-fouling performance, both towards protein adhesion as well as cell adhesion. Additionally, a bioorthogonal ligation strategy was performed in culture medium in the presence of cells showing a similar behavior for the three anti-fouling coatings, which indicates that this strategy can be applied for post-modification reactions in a complex environment.