Issue 8, 2022

Mitochondrion-targeting PEGylated BODIPY dyes for near-infrared cell imaging and photodynamic therapy

Abstract

A series of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-based photosensitizers (AmBXI, X = H, M, Br) featuring a cationic mitochondrion-targeting group and near-infrared (NIR) absorption was synthesized. After extending the photosensitizers’ π conjugation via Knoevenagel reaction, both the absorbance and emission maxima of AmBXI shifted to the phototherapeutic wavelength range (650–900 nm). Theoretical computations indicate that the introduction of bromine atoms promotes spin–orbit coupling, so that for each additional bromine atom in AmBXI an increase in singlet oxygen quantum yield would be expected (0.3%, 2.2%, and 4.1%, for AmBHI, AmBMI, and AmBBrI, respectively). Moreover, AmBXI photosensitizers exhibited low cytotoxicity in the dark and high phototoxicity, with the half maximal inhibitory concentrations of AmBBrI found to be 46.93 nM and 22.84 nM, while those of AmBMI were 129.7 nM and 58.34 nM in HeLa and MCF-7 cancer cells, respectively. Notably, introduction of a single bromine atom was enough to produce a cytotoxic effect. Furthermore, the presence of a quaternary ammonium group in AmBXI enabled the dyes to localize and stain the negatively charged mitochondria. The results presented herein indicate the straightforward and facile synthesis of NIR-light triggered mitochondrion-targeting photosensitizers.

Graphical abstract: Mitochondrion-targeting PEGylated BODIPY dyes for near-infrared cell imaging and photodynamic therapy

Supplementary files

Article information

Article type
Paper
Submitted
01 11 2021
Accepted
17 1 2022
First published
17 1 2022

J. Mater. Chem. B, 2022,10, 1196-1209

Mitochondrion-targeting PEGylated BODIPY dyes for near-infrared cell imaging and photodynamic therapy

I. W. Badon, C. Kim, J. M. Lim, D. K. Mai, T. P. Vales, D. Kang, S. Cho, J. Lee, H. Kim and J. Yang, J. Mater. Chem. B, 2022, 10, 1196 DOI: 10.1039/D1TB02393D

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