A novel amphiphilic copolymer was prepared by the copolymerization of N-acryloyl-3-aminophenylboronic acid with P-cyclodextrin containing maleic anhydride. The copolymer was fully characterized with C-13-NMR, H-1-NMR, IR, and scanning electron microscopy. The self-assembling mechanism of the copolymer in H2O-CH3OH cosolvents was studied. Gliclazide as a model drug was loaded inside the copolymer microspheres, and the drug-release behavior of the microspheres was studied. The results of in vitro oscillating release tests indicated that the microspheres responded to glucose rapidly in 30 min, and the microspheres exhibited self-regulated on-off release behavior four to six times in 6 h between the solution with 3 g/L glucose and the medium without glucose; this met the clinical requirements of multidrug delivery. (C) 2007 Wiley Periodicals, Inc.