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 Nov. 2021
Accepted
17 Janv. 2022
First published
17 Janv. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements