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The efficiency of photodynamic therapy (PDT) is related to the subcellular localization of photosensitizers (PSs) because organelles are associated with many fundamental life-sustaining activities. In this work, we synthesized a PS (CN) based on curcumin (CUR) and obtained enhanced PDT efficiency by simultaneously targeting lipid droplets (LDs) and the endoplasmic reticulum (ER). Compared with CUR, CN with a D–π–A–π–D structure possessed stronger intramolecular charge transfer features, resulting in longer absorption and emission wavelengths. In cell imaging experiments of CN using a confocal laser scanning microscope, a bright green emission in LDs and a weak orange emission in the ER were simultaneously observed due to its sensitivity to polarity. Surprisingly, CN with low singlet oxygen yields (0.13) exhibited an excellent photodynamic effect. Further experimental results showed that the phototoxicity of CN resulted in apoptosis by destroying the ER and ferroptosis by oxidizing polyunsaturated fatty acids (PUFAs) in LDs. This work paves the way for developing more effective photosensitizers with superior dual-targeting specificity. [ABSTRACT FROM AUTHOR]

Two photosensitizers (CCOH and CCN) were designed and synthesized by introducing coumarin into the curcumin (CUR) structure. Compared with CUR, more reactive oxygen species (ROS) were generated by CCOH and CCN in type I and II synergy upon light irradiation. Cell experiments indicated that CCN with an excellent LD-targeting effect could be used to monitor the changes in the morphology and number of LDs in tumor cells during PDT. [ABSTRACT FROM AUTHOR]