Synthesis, characterization, and biological activity of poly(vinyl saccharide)s and their sulfates: Biomimetics of glycosaminoglycans

One of the greatest challenges in biomaterials research lies in fabrication of soft materials for long term use in the human body that maintain integrity and biocompatibility while in contact with blood and tissue components. In order to generate novel biomaterials, a series of polymers, termed poly(vinyl saccharides) (PVS), were synthesized which display the carbohydrate moieties, glucose or galactose, pendent to the polymeric backbone. These polymers were further modified by sulfation of the carbohydrates to create novel polyelectrolytes. The structures of the PVS polymers were designed to mimic natural bioactive polysaccharides (e.g. heparin sulfate or chondroitin sulfate). PVS were studied as biologically active surface coatings by assessing their effects on various cell lines and blood proteins grown on or exposed to them.;Thrombin time coagulation assays using human plasma have shown the sulfated ester-linked glucose-PVS to have anticoagulant properties of 16 U/mg. Sulfated amide-linked glucose-PVS had 11 U/mg. Sulfated ester-linked galactose had 22 U/mg. Non-sulfated polymers had no activity. Platelet adhesion was lowered for glass modified with the sulfated polymers. Smooth muscle cell proliferation (DNA synthesis) was shown to be inhibited by the sulfated PVS. Hepatocytes were strongly adherent to the galactose polymer and the adhesion could be modulated by addition of sulfates.;High molecular weight polymers containing glucose were synthesized by free radical-initiated polymerization of 1,2:5,6-di-O-isopropylidene-3-0-methacryloyl-...