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.