Binding of 3-isobutyl-1-methylxanthine into copolymers of N-isopropylacrylamide.

Abstract

Linear and crosslinked copolymers based on N-isopropylacrylamide, NIPAAm, containing aromatic esters, have been synthesised. Vinyl benzoate and cinnamoyloxyethyl methacrylate have been used as aromatic comonomers. Certain aromatic esters are known of their capability to form molecular complexes with xanthines and thus, the purpose was to build up thermally responsive copolymers which specifically bind certain xanthines in aqueous solutions and release those under an influence of an environmental stimulus. The solutions of the linear copolymers have been studied in water in the presence of 3-isobutyl-1-methylxanthine, IBMX, as a function of drug concentration and temperature. The synthesised linear copolymers exhibited sensitivity to IBMX concentration in aqueous solutions above and below LCST, observed by viscosimetry and dynamic light scattering. The results are indicative of complex formation between the copolymers and IBMX. The crosslinked copolymers showed an increased IBMX binding capacity with an increasing amount of aromatic ester groups in the polymer network. IBMX release rates from the crosslinked gels were slowed down by the increasing degree of aromatic substitution, especially above LCST.