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

doi:10.1021/acs.analchem.8b03565

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

92 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 language	English
Pages (from-to)	12937-12943
Number of pages	7
Journal	Analytical Chemistry
Volume	90
Issue number	21
DOIs	https://doi.org/10.1021/acs.analchem.8b03565
State	Published - 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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title = "Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid",

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.",

author = "Pak, \{Yen Leng\} and Park, \{Sang Jun\} and Gyeongok Song and Yubin Yim and Hyuk Kang and Kim, \{Hwan Myung\} and Jean Bouffard and Juyoung Yoon",

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: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = nov,

day = "6",

doi = "10.1021/acs.analchem.8b03565",

language = "English",

volume = "90",

pages = "12937--12943",

journal = "Analytical Chemistry",

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T1 - Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid

AU - Pak, Yen Leng

AU - Park, Sang Jun

AU - Song, Gyeongok

AU - Yim, Yubin

AU - Kang, Hyuk

AU - Kim, Hwan Myung

AU - Bouffard, Jean

AU - Yoon, Juyoung

N1 - 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.

PY - 2018/11/6

Y1 - 2018/11/6

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85055715299

U2 - 10.1021/acs.analchem.8b03565

DO - 10.1021/acs.analchem.8b03565

M3 - Article

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AN - SCOPUS:85055715299

SN - 0003-2700

VL - 90

SP - 12937

EP - 12943

JO - Analytical Chemistry

JF - Analytical Chemistry

IS - 21

ER -

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

Abstract

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