Synthesis, development and biological properties of polyurethanes, quadrol and quadrol hydrogels

Initial controlled release studies and evaluations of the biological properties of a clear, flexible polyurethane elastomer (Sarathon) led to the serendipitous discovery of the macrophage activating (wound healing) properties of Quadrol. Mouse peritoneal macrophages when exposed to non-cytotoxic doses of Quadrol (1 and 4 mM) showed increased macrophage spreading. Quadrol-induced spreading was both concentration and time dependent and comparable to that of a lipopolysaccharide. Quadrol also showed increased macrophage phagocytosis of polystyrene beads. This increase was dose dependent with the best effect at 4 mM and peak activity at 30 minutes.;The synthesis of Quadrol-terminated and/or endcapped polyurethanes resulted in low molecular weight oligomeric materials. The surface modification of a hydroxyethyl methacrylate membrane led to a maximum of 10% Quadrol loading.;Two new monomer precursors, di- and trihydroxypropylated ethylenediamine, were prepared by the controlled reaction of propylene oxide with ethylenediamine. Then, water soluble, polymerizable, free radical monomers, Quadrol methacrylates, were synthesized by reacting glycidyl methacrylate with the above precursors. The interaction of Quadrol methacrylate (4 mM) with mouse peritoneal macrophages induced increased phagocytosis of polystyrene beads comparable to that of Quadrol. Clear, colorless poly(Quadrol-methacrylate) and poly(Quadrol-dimethacrylate) hydrogels were prepared by aqueous and/or bulk polymerization using redox initiation. These hydrogels were extremely hydrophilic. The polymer, free of residual monomer, formed a 1:1 complex between copper(II) and the Quadrol contained in the polymer as opposed to the literature values of 1:1 or 1:2. Co-polymerization with hydroxyethyl methacrylate, a water miscible monomer, gave hydrogels with varying hydrophilicity.