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Herein, a smart interactive system (G\u2282H) consisting of a hypoxia\u2010acid dual triggered multifunctional guest (G) and an amphipathic metal\u2010organic capsule (H) was successfully established for bioimaging and treatment. Hydrophobic G is encapsulated in cavity of H to form the homogeneous soluble G\u2282H, which enhances its accumulation in tumor cells, controls the interactive regulation between G\u2282H and TME, and facilitates the sensitivity of tumor cell therapy. When triggered in TME, G\u2282H selectively releases an alkylating agent and a doxifluridine (DFUR) via the activation of azo and ketal linkers for multidrug chemotherapy, and the fluorescence emission from the activated G\u2282H is used for real\u2010time release visualization of the hypoxia\u2010activating drug in cell substructure and hypoxia imaging. Owing to its homogeneous delivery, TME regulation and TME response properties toward the hypoxia tumor cells, G\u2282H exhibits significantly higher toxicity in a hypoxic environment (0.1% O\n                    <jats:sub>2<\/jats:sub>\n                    ) than that in normoxia. As expected, G\u2282H performs good imaging capability and treatment effect in hypoxia tumor cells, flow cytometry assay and tumor\u2010bearing mice, implying its great potential in bioimaging and multidrug synergistic therapy.\n                  <\/jats:p>","DOI":"10.1002\/smll.75445","type":"journal-article","created":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T11:09:31Z","timestamp":1791284971000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Smart Interactive System for the Enhanced Bioimaging and Multi\u2010Drug Synergistic Therapy in Tumor\u2010Microenvironment"],"prefix":"10.1002","volume":"22","author":[{"given":"Lei","family":"Zhang","sequence":"first","affiliation":[{"name":"State Key Laboratory of Fine Chemicals School of Chemical Engineering Dalian University of Technology  Dalian 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