Abstract
A series of four lactose-modified BODIPY photosensitizers (PSs) with different substituents (-I, -H, -OCH3, and -NO2) in the para-phenyl moiety attached to the meso-position of the BODIPY core were synthesized; the photophysical properties and photodynamic anticancer activities of these sensitizers were investigated, focusing on the electronic properties of the different substituent groups. Compared to parent BODIPY H, iodine substitution (BODIPY I) enhanced the intersystem crossing (ISC) to produce singlet oxygen (1O2) due to the heavy atom effect, and maintained a high fluorescence quantum yield (ΦF) of 0.45. Substitution with the electron-donating methoxy group (BODIPY OMe) results in a significant perturbation of occupied frontier molecular orbitals and consequently achieves higher 1O2 generation capability with a high ΦF of 0.49, while substitution with the electron-withdrawing nitro group (BODIPY NO2) led a perturbation of unoccupied frontier molecular orbitals and induces a forbidden dark S1 state, which is negative for both fluorescence and 1O2 generation efficiencies. The BODIPY PSs formed water-soluble nanoparticles (NPs) functionalized with lactose as liver cancer-targeting ligands. BODIPY I and OMe NPs showed good fluorescence imaging and PDT activity against various tumor cells (HeLa and Huh-7 cells). Collectively, the BODIPY NPs demonstrated high 1O2 generation capability and ΦF may create a new opportunity to develop useful imaging-guided PDT agents for tumor cells.
Highlights
A series of four lactose-modified BODIPY photosensitizers (PSs) with different substituents (-I, -H, -OCH3, and -NO2) in the para-phenyl moiety attached to the meso-position of the BODIPY core were synthesized; the photophysical properties and photodynamic anticancer activities of these sensitizers were investigated, focusing on the electronic properties of the different substituent groups
We synthesized four BODIPY PSs containing different substituent groups (-I, -H, -OCH3, and -NO2) in the para-phenyl moiety attached to the meso-position of the BODIPY core, and investigated their photophysical and photosensitizing properties according to the variation in the substituents
Φ△ could be enhanced to 0.03 in a less polar solvent (THF). Such finding indicates that the triplet state of BODIPY NO2 is strongly affected by the polarity of the media. These results collectively indicate that both iodinated- meso-phenyl BODIPY I and heavy-free atom BODIPY OMe achieved an elevated 1O2 under light-emitting diode (LED) illumination that facilitated singlet oxygen generation, demonstrating their potential use as efficient photosensitizers for Photodynamic therapy (PDT)
Summary
A series of four lactose-modified BODIPY photosensitizers (PSs) with different substituents (-I, -H, -OCH3, and -NO2) in the para-phenyl moiety attached to the meso-position of the BODIPY core were synthesized; the photophysical properties and photodynamic anticancer activities of these sensitizers were investigated, focusing on the electronic properties of the different substituent groups. BODIPY I and OMe NPs showed good fluorescence imaging and PDT activity against various tumor cells (HeLa and Huh-7 cells). The BODIPY NPs demonstrated high 1O2 generation capability and ΦF may create a new opportunity to develop useful imaging-guided PDT agents for tumor cells. We reported a series of water-soluble BODIPY PSs attached to heavy atoms at the 2,6-position of the BODIPY c ore[24] These BODIPY PSs showed excellent PDT ability, while exhibiting very low dark toxicity; they could not be used as imaging reagents due to their low fluorescence quantum yield (ΦF) resulting from the incorporation of heavy atoms. Our findings indicate that BODIPY NPs are promising tumor-targeted PDT agents, with fluorescence cell imaging properties in live cancer cell lines
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