biostudies-literatureUnknown14(13)Zheng XThe photosensitizers (PSs) for photodynamic therapy (PDT) mostly possess conjugated skeletons that are over-sized and poorly water-soluble to be encapsulated by conventional macrocyclic receptors. Herein, we report that two fluorescent hydrophilic cyclophanes, AnBox·4Cl and ExAnBox·4Cl, can effectively bind hypocrellin B (HB), a pharmaceutically active natural PS for PDT, with binding constants of the 107 level in aqueous solutions. The two macrocycles feature extended electron-deficient cavities and can be facilely synthesized through photo-induced ring expansions. The corresponding supramolecular PSs (HB⊂AnBox4+ and HB⊂ExAnBox4+) exhibit desirable stability, biocompatibility, and cellular delivery, as well as excellent PDT efficiency against cancer cells. In addition, living cell imagingChemical science3523-3530https://www.ebi.ac.uk/biostudies/studies/S-EPMC10055832biostudies-literatureSupramolecular photosensitizers using extended macrocyclic hosts for photodynamic therapy with distinct cellular delivery† † Electronic supplementary information (ESI) available: General information, synthesis and characterization, host–guest chemistry, photodynamic therapy related cell experiments, and DFT calculations. See DOI: https://doi.org/10.1039/d3sc00107ePMC10055832Zheng XWu LWang PDong XTung CXiao HGao ZCong HLei SLiu WfalseSupramolecular photosensitizers using extended macrocyclic hosts for photodynamic therapy with distinct cellular delivery† † Electronic supplementary information (ESI) available: General information, synthesis and characterization, host–guest chemistry, photodynamic therapy related cell experiments, and DFT calculations. See DOI: https://doi.org/10.1039/d3sc00107eThe photosensitizers (PSs) for photodynamic therapy (PDT) mostly possess conjugated skeletons that are over-sized and poorly water-soluble to be encapsulated by conventional macrocyclic receptors. Herein, we report that two fluorescent hydrophilic cyclophanes, AnBox·4Cl and ExAnBox·4Cl, can effectively bind hypocrellin B (HB), a pharmaceutically active natural PS for PDT, with binding constants of the 107 level in aqueous solutions. The two macrocycles feature extended electron-deficient cavities and can be facilely synthesized through photo-induced ring expansions. The corresponding supramolecular PSs (HB⊂AnBox4+ and HB⊂ExAnBox4+) exhibit desirable stability, biocompatibility, and cellular delivery, as well as excellent PDT efficiency against cancer cells. In addition, living cell imaging2023-01-01T00:00:00Z2023 Mar2025-04-04T14:50:57.342Z2024-11-13T07:14:33.981ZS-EPMC10055832