Poly (amidoamine) (PAMAM) dendrimer-release multilayer films were prepared using phenylboronic acid-modified PAMAM dendrimers (PBA-D) and poly (vinyl alcohol) (PVA) through boronate ester bonds. The (PBA-D/PVA)10 film was stable in pH 9.0 solution. Upon addition of H2O2, PAMAM dendrimers were released from the (PBA-D/PVA)10 film due to oxidative scission of the carbon-boron bond in the PBA residues in PBA-D. For example, 75 and 90% of the PBA-D was released from the (PBA-D/PVA)10 film within 30 min of exposure to 0.5 and 1 mM H2O2, respectively. In addition, (PBA-D/PVA)10 films containing glucose oxidase responded to the presence of 1 mM glucose in pH 7.4 solution due to the enzymatic production of H2O2.