The shell cross-linked micelles composed of tyramine-conjugated 4-arm poly(propylene oxide)–poly(ethylene oxide) was developed as a carrier for controlled drug delivery. The shell cross-linked tyramine-conjugated 4-arm poly(propylene oxide)–poly(ethylene oxide) micelles were prepared by an enzyme-mediated reaction using horseradish peroxidase and hydrogen peroxide. The physicochemical properties, size distribution, morphologies, and thermal properties of the shell cross-linked tyramine-conjugated 4-arm poly(propylene oxide)–poly(ethylene oxide) micelles were characterized to confirm the micelle formation and controllable properties dependent on the concentration of the catalysts. The in vitro cytocompatibility of the micelles was investigated using NIH3T3 fibroblast cells, and the shell cross-linked tyramine-conjugated 4-arm poly(propylene oxide)–poly(ethylene oxide) micelles showed low cytotoxicity. The in vitro hydrophobic drug release behavior from the shell cross-linked tyramine-conjugated 4-arm poly(propylene oxide)–poly(ethylene oxide) micelles was controllable with a sustained release behavior. Therefore, the shell cross-linked tyramine-conjugated 4-arm poly(propylene oxide)–poly(ethylene oxide) micelles via enzyme-mediated reaction have potential as nanocarriers for controlled drug delivery.
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