Versatile surface biofunctionalization of poly(ethylene terephthalate) by interpenetrating polymerization of a butynyl monomer followed by “Click Chemistry”

Abstract

Biofunctionalization of poly(ethylene terephthalate) (PET) is crucial to its medical and biomedical applications such as surgical drapes, vascular grafts and ligament prostheses. To furnish PET with an alkynyl handle, N-(2-methylbut-3-yn-2-yl)acrylamide (MBAA) underwent photo-initiated copolymerization with N,N0-methylenebisacrylamide (MBA) in methanol-swollen PET surface to form a 3- dimensional interpenetrating network (IPN). The alkynyl handle terminated surface was denoted as PMBAA-PET. A region-selective modification could be achieved using an engraved mask during the photo-initiated copolymerization. Several functional azides including dansyl-azide 1, azido-5,5- dimethyl-hydantoin analog 2, per-azido-b-cyclodextrin (per-azido-b-CD) and azido-Bovine Serum Albumin (BSA-N3), were successfully bonded onto PMBAA-PET surface via Huisgen 1,3-dipolar cycloaddition. Kinetic study of the heterogeneous “click” reaction between PMBAA-PET and 1 was investigated using X-ray photoelectron spectroscopy (XPS) and elemental analysis. PMBAA-PET was rendered with effective biocidal activity against a healthcare-associated methicilin-resistant Staphylococcus aureus (HAMRSA) and a multi-drug-resistant Escherichia coli (MDR-E. coli) after 2 was conferred. Meanwhile, accessible CD cavity was determined and the amount of covalently immobilized BSA protein was also quantified after the respective “click” linkages of per-azido-b-CD and BSA-N3 on PMBAA-PET surface were established.