Issue 43, 2019

BODIPY-based selenides as fluorescent probes for rapid, sensitive and mitochondria-specific detection of hypochlorous acid

Abstract

Hypochlorous acid (HClO) is a powerful microbicidal agent in the innate immue system; however, abnormal HClO levels can cause tissue damage and many diseases. Thus, it is vitally important to develop facile, rapid and accurate analytical methods for the detection of HClO/ClOin vitro and in vivo. In this work, we have constructed three meso-substituted BODIPY selenides with different hydrocarbyl groups (ethyl for BSe-Et, benzyl for BSe-Bz and phenyl for BSe-Ph) as fluorescent probes for the detection of HClO/ClO. All three non-fluorescent probes can sense HClO/ClO to form fluorescent selenoxides by blocking the photo-induced electron transfer process. Their sensing properties display a clear relationship with the structure of the hydrocarbyl. The sensing reactivity is heavily dependent on the electron-donating ability of hydrocarbyls, with the order of the response time as BSe-Et (2 s) < BSe-Bz (5 s) ≪ BSe-Ph (>100 s). Both BSe-Et and BSe-Bz afford a large fluorescence response and very low detection limits (0.3 nM and 0.8 nM), and BSe-Bz displays a higher selectivity over BSe-Et. Finally, as a representative, BSe-Bz was successfully applied to the detection of exo- and endogenous HClO in living cells, and demonstrated to be a mitochondria-localized fluorescent probe.

Graphical abstract: BODIPY-based selenides as fluorescent probes for rapid, sensitive and mitochondria-specific detection of hypochlorous acid

Supplementary files

Article information

Article type
Paper
Submitted
04 Aug 2019
Accepted
30 Sep 2019
First published
02 Oct 2019

J. Mater. Chem. B, 2019,7, 6861-6867

BODIPY-based selenides as fluorescent probes for rapid, sensitive and mitochondria-specific detection of hypochlorous acid

X. Xu, C. Liu, Y. Mei and Q. Song, J. Mater. Chem. B, 2019, 7, 6861 DOI: 10.1039/C9TB01641D

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