Photosensitizer synergistic effects: D–A–D structured organic molecule with enhanced fluorescence and singlet oxygen quantum yield for photodynamic therapy

摘要

The development of photosensitizers with high fluorescence intensity and singlet oxygen (¹O2) quantum yields (QYs) is of great importance for cancer diagnosis and photodynamic therapy (PDT). Diketopyrrolopyrrole (DPP) and boron dipyrromethene (BODIPY) are two kinds of building block with great potential for PDT. Herein, a novel donor–acceptor–donor (D–A–D) structured organic photosensitizer DPPBDPI with a benzene ring as a π bridge linking DPP and BODIPY has been designed and synthesized. The results indicate that the combination of DPP with BODIPY can simultaneously increase the fluorescence QY (5.0%) and the ¹O2 QY (up to 80%) significantly by the synergistic effect of the two photosensitizers. By nanoprecipitation, DPPBDPI can form uniform nanoparticles (NPs) with a diameter of less than 100 nm. The obtained NPs not only exhibit high photo-toxicity, but also present negligible dark toxicity towards HeLa cells, demonstrating their excellent photodynamic therapeutic efficacy. In vivo fluorescence imaging shows that DPPBDPI NPs can target the tumor site quickly with the enhanced permeability and retention (EPR) effect and can effectively inhibit tumor growth using photodynamic therapy even with low doses (0.5 mg kg^–1). The enhanced imaging and photodynamic performance of DPPBDPI suggest that the synergistic effect of DPP and BODIPY provides a novel theranostic platform for cancer diagnosis and photodynamic therapy.