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Herein, we synthesized a pyridinium\u2010decorated diiodo\u2010BODIPY compound (PyBDP) and investigated its photosensitizing activity under hypoxic condition in the presence of NADH that is abundant in the mitochondria of hypoxic tumors. The unique property of PyBDP lies in the redox environment\u2010dependent photo\u2010response. At green light exposure, PyBDP is converted into a colorless inactive form by interacting with NADH in a two\u2010step one\u2010electron transfer process. Interestingly, the NADH\u2010dependent hydrogenation of PyBDP is affected by the presence of cytochrome c (Cyt <jats:italic>c<\/jats:italic><jats:sub>ox<\/jats:sub>) that is an important component of mitochondrial electron transport chain (Mito\u2010ETC), unless Cyt <jats:italic>c<\/jats:italic><jats:sub>ox<\/jats:sub> is exhausted. Active radical species is produced during the photocatalytic reaction, which adds the understanding of PyBDP\u2010induced photodamage. Therefore, we applied the strategy of auto\u2010deactivation PDT using a BODIPY photosensitizer by tethering triphenylphosphonium to PyBDP. After PDT effect in a type I pathway, the photosensitizer underwent almost entire auto\u2010deactivation in hypoxic HeLa cells. This work paves a way for the development of reductive PDT with enhanced safety and efficacy in fighting hypoxic tumors independent on reactive oxygen species (ROS).<\/jats:p>","DOI":"10.1002\/cbic.202400767","type":"journal-article","created":{"date-parts":[[2024,11,19]],"date-time":"2024-11-19T22:31:24Z","timestamp":1732055484000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Auto\u2010Deactivation of BODIPY\u2010Derived Type I Photosensitizer Post Photodynamic Therapy under Hypoxia"],"prefix":"10.1002","volume":"26","author":[{"given":"Xia","family":"Wang","sequence":"first","affiliation":[{"name":"MOE Key Laboratory of High Performance Polymer Material and Technology of Ministry of Education Department of Polymer Science &amp; Engineering, School of Chemistry &amp; Chemical Engineering Nanjing University  Jiangsu, Nanjing 210023 P. R. 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