Novel acrylic monomers (beta-CD-A and beta-CD-6-EA) containing beta-cyclodextrin (beta-CD) with different extent of substitution were prepared by using dicyclohexylcarbodiimide (DCC) as a condensation agent at room temperature. Two kinds of functional hydrogels were also synthesized by copolymerization of beta-CD-A and beta-CD-6-EA with acrylic acid (AAc) using a redox initiator system in aqueous solution. The nuclear magnetic resonance (H-1 NMR), infrared spectroscopy (IR), thermogravimetric analysis (TGA) were employed to character the molecular structures of beta-CD modified monomers and their copolymers. The swelling experiments indicate that the hydrogels with different equilibrium swelling ratio (ESR) possess obvious pH-sensitivity and distinct dynamic swelling behavior. Using an anti-cancer drug, chlorambucil (CHL), able to form complexes with beta-CD in water, as a model Compound, the controlled drug release behaviors of these hydrogels were investigated. The release behavior of CHL from two kinds of hydrogels synthesized reveals that the release rate of CHL can be effectively controlled by pH values, cross-linking density, and beta-CD content. In addition, it is found that the beta-CD with the proper frame and concentration can increase release efficiency of CHL from the hydrogels. (C) 2009 Wiley Periodicals, Inc. J Appl Polym Sci 113: 3068-3077, 2009