Coupling BODIPY with nitrogen-doped graphene quantum dots to address the water solubility of photosensitizers
The potential of photodynamic therapy (PDT) applications is based primarily on the selection of suitable photosensitizers (PSs). However, highly efficient PSs producing singlet oxygen and other reactive oxygen species (ROS) often have poor water solubility and tend to aggregate in biological media. The most common alternative strategy to address the solubility of PSs is based on difficult-to-control encapsulation or conjugation to liposomes, micelles, or other nanoparticles via surface non-covalent interactions. Covalent functionalization remains relatively unexplored for common PSs. Here, we report a strategy to use highly efficient but poorly water-soluble BODIPY PSs connected to the surface of nitrogen-doped graphene quantum dots (NGQDs) through controlled covalent functionalization. These NGQD–BODIPY PSs do not aggregate in aqueous solutions and generate ROS upon irradiation with visible light, with singlet-oxygen production quantum yields up to 83%. In vitro fluorescence bioimaging was used to confirm that the PSs reside mostly in the cytoplasmic region of human cervical cancer cells (HeLa), and the system reduced the cell viability by B85% upon irradiation.
This work was supported by the Operational Program Research, Development, and Education-Project ‘MSCAfellow4@MUNI’ (No. CZ.02.2.69/0.0/0.0/20_079/0017045). We acknowledge CzechNanoLab Research Infrastructure (LM2018110), supported by the Ministry of Education, Youth and Sports of the Czech Republic (MEYS CR). We also acknowledge the support by the Strategy of the Czech Academy of Sciences program Qualitas (68081707). P. K. thanks the RECETOX Research Infrastructure (No. LM2018121) financed by the Ministry of Education, Youth and Sports, and the Operational Programme Research, Development and Education (the CETOCOEN EXCELLENCE project No. CZ.02.1.01/0.0/0.0/17_043/0009632) for supportive background. This project was also supported by the European Union’s Horizon 2020 Research and Innovation Programme under grant agreement No. 857560. This publication reflects only the authors’ view, and the European Commission is not responsible for any use that may be made of the information it contains. We are grateful to Prof. Vladimı´r Sˇindela´rˇ for allowing us to use the MW reactor, supported by the RECETOX research infrastructure (via MEYS CR under LM2018121).
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