Functionalized derivatives of hyaluronic acid oligosaccharides: drug carriers and novel biomaterials.

Oligosaccharides derived from hyaluronic acid (HA), a naturally occurring linear polysaccharide composed of repeating disaccharide units of N-acetyl-D-glucosamine and D-glucuronic acid, can be chemically modified to introduce a pendant amine-like functionality (patent application pending). Covalent attachment of steroidal and nonsteroidal antiinflammatory drugs to functionalized HA oligosaccharides was accomplished with the incorporation of hydrolytically labile bonds. Further derivatization of the pendant group with homobifunctional crosslinkers allowed the introduction of covalent crosslinks. Chemically-modified HA oligosaccharides were unambiguously characterized in solution by high-resolution 1H NMR spectroscopy.