BODIPY precursors and their cyclotriphosphazene Derivatives: Synthesis, photochemical properties and their application in PDT

[Display omitted] •Design and synthesis of novel Cyclotriphosphazene-BODIPY Derivatives.•Photochemical properties of the compounds.•Singlet oxygen measurements of the compounds.•In vitro anti-cancer efficiencies of the novel compounds in the absence and presence of red-light illumination. Photodynamic therapy (PDT) is a treatment method consisting of common combination of oxygen, light energy and a light absorbing molecule called a photosensitizer. In this work, four new compounds consisting of BODIPY precursors and BODIPY-cyclotriphosphazene derivatives were synthesized to investigate the PDT effects. The chemical structures of the compounds were characterized and then their photophysical properties were determined by spectroscopic techniques. The precursor BODIPYs and their cyclotriphosphazene derivatives exhibited similar properties such as strong absorption intensity, high photostability and low fluorescence profile in the NIR region. Additionally, the singlet oxygen production capacities of these compounds were determined using the photobleaching technique of 1,3-diphenylisobenzofuran (DPBF) under light illumination. By introducing iodine atoms into the molecule, which are responsible for the intersystem transition (ISC) enhancement, a more efficient singlet oxygen production was achieved in both the iodinated-BODIPY and its cyclotriphosphazene derivative. Anticancer activities of the precursor BODIPYs and their cyclotriphosphazene derivatives in the absence and presence of light illumination were evaluated on cancerous cell lines (PC3 and DU145) and non-tumorigenic prostate epithelial PNT1a cell. The compounds triggered the death of cancer cell PC3 the more significantly in the presence of red light compared to the healthy cells (PNT1a).