Studies of some new bioactive acrylic esters

AbstractFour typical bioactive esters of acrylic monomers, N‐p‐acryloxybenzoyloxysuccinimides, 3‐ac‐ryloxy‐4‐oxo‐3,4‐dihydro‐1,2,3‐benzotriazines, N‐acryloxy‐5‐norbornene‐2,3‐dicarboximides, and I‐p‐acryloxybenzoyloxybenzotriazoles, were Synthesized and polymerized as reactive polymers. Twelve new monomers were prepared by coupling acrylic acid, methacrylic acid, p‐acryloxybenzoic acid, or p‐methacryloxybenzoic acid with four N‐hydroxy compounds such as N‐hydroxysuccinimide (HOSu), 3‐hydroxy‐4‐oxo‐3,4‐dihydro‐1,2,3‐benzotriazine (HOObt), N‐hydroxy‐5‐norbornene‐2,3‐dicarboximide (HONB), and I ‐hydroxybenzotriazole (HOBT) in the presence of dicyclohexylcarbodimide. All monomers polymerized readily in solution with azobisisobutyronitrile (AIBN) as free radical initiator. The resulting reactive polymers with reactive OSu, OObt, ONB, or OBT group on the side chain are equally reactive toward n‐butylamine at room temperature in the formation of corresponding polyacrylamides. Reactive polymers were used to immobilizetrypsin. It has been found that poly(N‐p‐methacryloxybenzoyloxy‐5‐norbornene‐2,3‐dicarboximide)‐trypsin matrix had high activity around three times that of the poly(N‐methacryloxy‐5‐norbornene‐dicarboximide)‐trypsin matrix. It is proposed that this activity may be due to the presence of a long spacer arm with a hydrophobic and rigid benzene ring between the ligand and matrix. The reactive poly(N‐p‐methacryloxybenzoyloxysuccinimide‐p‐methacryloxybenzoic acid) copolymer was used to immobilize the serum protein. This immobilized protein was a hopeful bioactive solid immunoadsorbent.