A fluorescent turn-on probe for detection of hypochlorus acid and its bioimaging in living cells

Chien-Ju Chu; Guan-Syuan Wu; Ho-I Ma; Parthiban Venkatesan; Natesan Thirumalaivasan; Shu-Pao Wu

doi:10.1016/j.saa.2020.118234

A fluorescent turn-on probe for detection of hypochlorus acid and its bioimaging in living cells

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Jun 5:233:118234. doi: 10.1016/j.saa.2020.118234. Epub 2020 Mar 5.

Authors

Chien-Ju Chu¹, Guan-Syuan Wu¹, Ho-I Ma¹, Parthiban Venkatesan¹, Natesan Thirumalaivasan¹, Shu-Pao Wu²

Affiliations

¹ Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan.
² Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan. Electronic address: spwu@mail.nctu.edu.tw.

PMID: 32163873
DOI: 10.1016/j.saa.2020.118234

Abstract

Hypochlorous acid has played several functions in the biological system. However, excess HOCl can cause damage to biomolecules and result in some diseases. Accordingly, a new fluorescent probe, BSP, has been developed for fast recognition of HOCl through the HOCl-induced oxidation of methyl phenyl sulfide to sulfoxide. The reaction of BSP with HOCl caused a 22-fold fluorescence enhancement (quantum yield increase from 0.006 to 0.133). The detection limit of HOCl is found to be 30 nM (S/N = 3). The fluorescence enhancement is due to the suppression of the photo-induced electron transfer from the methyl phenyl sulfide moiety to BODIPY. Eventually, the cellular fluorescence imaging experiment showed that BSP could be effectively used for monitoring HOCl in living cells.

Keywords: BODIPY; Cell imaging; Fluorescent probe; HOCl.

MeSH terms

Animals
Fluorescent Dyes / chemistry*
Hypochlorous Acid* / analysis
Hypochlorous Acid* / metabolism
Mice
Microscopy, Fluorescence
Oxidation-Reduction
RAW 264.7 Cells
Safrole / analogs & derivatives
Safrole / chemistry
Sulfides / chemistry

Substances

Fluorescent Dyes
Sulfides
Hypochlorous Acid
methylphenylsulfide
Safrole
sulfoxide