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....

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Bibliographic Details
Published in:Materials chemistry frontiers 2022-06, Vol.6 (12), p.1719-1726
Main Authors: Jénnifer Gómez, I, Russo, Marina, Arcidiacono, Orazio Angelo, Sánchez-Carnerero, Esther M, Klán, Petr, Zají ková, Lenka
Format: Article
Language:English
Subjects:
Aqueous solutions
Conjugation
Covalence
Graphene
Irradiation
Medical imaging
Micelles
Nanoparticles
Nitrogen
Oxygen production
Photodynamic therapy
Quantum dots
Singlet oxygen
Solubility
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Summary: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 ∼85% upon irradiation. Water-soluble photosensitizers based on covalently grafted nitrogen-doped graphene quantum dot-BODIPY for cellular imaging and photodynamic therapy.
ISSN:2052-1537
2052-1537
DOI:10.1039/d2qm00200k