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BODIPY-Based Fluorescent Surfactant for Cell Membrane Imaging and Photodynamic Therapy
journal contribution
posted on 2019-12-12, 19:08 authored by Hua Wang, Weiwei Zhao, Xiaoyan Liu, Shu Wang, Yilin WangFluorescent dyes are widely used in chemical, biological,
and environmental science. However, the π–π stacking
among the large π-conjugated groups of the dye molecules normally
leads to the hydrophobicity and aggregation, resulting in quenching
the fluorescence intensity. In the present work, a kind of BODIPY-based
fluorescent surfactant C8BCOONa has been synthesized, and its self-assembly
and performances in cell membrane imaging and photodynamic therapy
have been studied. This fluorescent surfactant exhibits low critical
micellar concentration (CMC) in aqueous solution and forms vesicles
above the CMC. The fluorescence intensity of C8BCOONa significantly
increases with aggregating into the DOPC vesicles, in which C8BCOONa
inserts into the bilayer of DOPC vesicles through hydrophobic interaction
and the intramolecular rotation of C8BCOONa is restrained in the aggregates.
The fluorescent surfactant of low concentration displays negligible
dark- and photocytotoxicity to MCF-7 cells and HeLa cells and can
effectively stain the living cell membrane with a long retention time.
Meanwhile, a large amount of reactive oxygen species is generated
by higher concentration C8BCOONa under white light and brings obvious
photocytotoxicity to the two types of cancer cells. Therefore, this
kind of fluorescent surfactant shows a great potential in targeted
bioimaging and efficient photodynamic therapy.