Biodegradable molecularly imprinted polymers based on poly(ε-caprolactone)

Abstract

Novel biodegradable molecularly imprinted polymers (MIPs) based on poly(e-caprolactone) (PCL) were prepared by combining two important properties required of ideal biomaterials, biodegradability (with biocompatibility) and molecular recognition properties. Acrylate or methacrylate end-capped PCL macromers were synthesized through the reaction of PCL diol or triol with acryloyl or methacryloyl chloride. The synthesis of acrylate or methacrylate end-capped macromers was confirmed using FT-IR and H NMR spectroscopic techniques. These macromers were used to prepare biodegradable crosslinked networks by photopolymerization with functional monomer (acrylic acid) and a model template (theophylline). The theophylline-imprinted polymer showed higher binding capacity for theophylline compared with non-imprinted polymer (NIP), and also showed selectivity for theophylline over caffeine (similar structure molecules). PCL-based MIP degraded 8% of the initial weight in 30 days in phosphate-buffered saline (PBS) solution (pH 7.4) and over 90% of the initial weight within 24 h in 1 N NaOH at 37°C.