Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid

Yen Leng Pak, Sang Jun Park, Gyeongok Song, Yubin Yim, Hyuk Kang, Hwan Myung Kim, Jean Bouffard, Juyoung Yoon

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

The naphthoimidazolium borane 4 is shown to be a selective probe for HOCl over other reactive oxygen species. Unlike other boronate-reactive oxygen species (ROS) fluorogenic probes that are oxidized by HOCl through a nucleophilic borono-Dakin oxidation mechanism, probe 4 is distinguished by its electrophilic oxidation mechanism involving B-H bond cleavage. Two-photon microscopy experiments in living cells and tissues with the probe 4 demonstrate the monitoring of endogenous HOCl generation and changes in HOCl concentrations generated in the endoplasmic reticulum during oxidative stress situations.

Original languageEnglish
Pages (from-to)12937-12943
Number of pages7
JournalAnalytical Chemistry
Volume90
Issue number21
DOIs
StatePublished - 6 Nov 2018

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea for the financial support (2012R1A3A2048814 to J.Y., 2016-R1E1A1A02920873 to H.M.K., and 2018R1D1A1B07043568 to J.B.). We also thank the Western Seoul (LC−MS) and Daegu (FAB) branches of the Korea Basic Science Institute for mass spectrometric data.

Publisher Copyright:
© 2018 American Chemical Society.

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