N-(2-HYDROXYPROPYL) METHACRYLAMIDE COPOLYMERS CONTAINING PENDANT SACCHARIDE MOIETIES - SYNTHESIS AND BIOADHESIVE PROPERTIES

A new route for the synthesis of bioadhesive water soluble polymeric drug carriers has been developed. Novel monomers, namely, N-methacryloylglycylglycylgalactosamine (MA-Gly-Gly-GalN) [8], MA-Gly-Gly-FucN [9], MA-Gly-Gly-GlcN [10], and MA-Gly-Gly-ManN [11], and copolymers [12-16] based on N-(2-hydroxypropyl)methacrylamide (HPMA) containing different content of pendant saccharide moieties (galactosamine, fucosylamine, glucosamine, or mannosamine), were synthesized. Copolymerization parameters for the copolymerization of HPMA [M1] and MA-Gly-Gly-GalN [M2] have been determined (r1 = 0.82, r2 = 0.38). Bioadhesion studies with everted sacs of guinea pig small intestine and colon in vitro demonstrated that HPMA copolymers containing side-chains terminated in fucosylamine bind selectively to the colonic tissue. The extent of binding was dependent on the fucosylamine content of copolymers.