Abstract: Amphiphilic block copolymer polyethylene glycol-b-di(2-acryloyloxy ethoxy-4-methoxy-phenylmethane) (PEG-b-PACDs) was successfully synthesized by deactivation enhanced atom transfer radical polymerization (DE-ATRP) with brominated polyethylene glycol (PEG2KBr) as a macromolecular initiator and di (2-acry-loyloxy ethoxy)-4-methoxy-phenylmethane as an acid-cleavable divinyl (ACD) monomers. The polymer was self-assembled by drip water method to form micelles, and the drug chlorin e6 (Ce6) was loaded into micelles to generate drug-loaded micelles. The structural characteristics of the polymer were analyzed by nuclear magnetic resonance hydrogen spectroscopy (¹H-NMR). The polymer with acetal structure could be hydrolyzed to aldehydes and alcohols under acidic conditions. The polymer retains olefinic bond, thus had a novel glutathione (GSH) responsive through the Michael addition reaction between GSH and olefinic bond. The size and morphology of the self-assembled blank micelles and Ce6-loaded micelles were characterized by Dynamic Light Scattering (DLS) and transmission electron microscope (TEM), which showed that both blank micelles and Ce6-loaded micelles can form uniform spherical micelles. The drug loading content of Ce6-loaded micelles could reach 6.04%. The sustained release of Ce6 from Ce6-loaded micelles in vitro clearly showed that Ce6-loaded micelles exhibited dual-stimuli responses by acid and GSH leading to controlled drug release behavior. In addition, the cytotoxicity of the drug-loaded micelles was verified by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay. The cytotoxicity experiments also demonstrated that the Ce6-loaded micelles had a good photodynamic therapy (PDT) effect on cancer cells.