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Herein, we proposed a simple tactic of side-chain sulfonation to construct the subcellular organelles targeting type I PS. Initially, the traditional lipophilic donor-\u03c0-acceptor (D-\u03c0-A) system (3SSYDI) was constructed, which exhibited type II reactive oxygen species generation capability and lipid droplets (LDs)-targeting property. Innovatively, the heavy-atom-free sulfonate ion was introduced to achieve side-chain sulfonation. The modulated 3SSYDS not only exhibited optimal biosafety but also possessed lower impedance and higher photocurrent intensity, which facilitated superior electron transfer to generate superoxide anions (O2\u2013\u2022). Notably, in biological aqueous systems, O2\u2013\u2022 combined with protons to further produce hydrogen peroxide, thereby triggering the Haber\u2013Weiss reaction to produce the most reactive hydroxyl radical (\u2022OH), achieving more effective suppression of cancer cells even under hypoxic conditions. This study presents a simple strategy of side-chain sulfonation that activated highly toxic \u2022OH generation in traditional D-\u03c0-A systems, providing an efficient solution for treating hypoxic tumors.<\/jats:p>","DOI":"10.1021\/acsabm.5c01612","type":"journal-article","created":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T11:32:13Z","timestamp":1760355133000},"page":"10325-10333","source":"Crossref","is-referenced-by-count":0,"title":["Side-Chain Sulfonation\nto Modulate Hydroxyl Radical\nGenerators for Efficient Suppression of Hepatoma Cells under Hypoxia"],"prefix":"10.1021","volume":"8","author":[{"given":"Shouchi","family":"Ji","sequence":"first","affiliation":[{"name":"Anhui University , , ,","place":["Hefei, P. R. China, 230601"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junjun","family":"Wang","sequence":"additional","affiliation":[{"name":"Hefei Normal University , , ,","place":["Hefei, P. R. 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