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 guinesa 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.