A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria

Qingling Xu; Cheol Ho Heo; Jin A. Kim; Hye Sue Lee; Ying Hu; Dayoung Kim; Kunemadihalli Mathada Kotraiah Swamy; Gyoungmi Kim; Sang Jip Nam; Hwan Myung Kim; Juyoung Yoon

doi:10.1021/acs.analchem.6b01738

A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria

Qingling Xu
, Cheol Ho Heo
, Jin A. Kim
, Hye Sue Lee
, Ying Hu
, Dayoung Kim
, Kunemadihalli Mathada Kotraiah Swamy
, Gyoungmi Kim
, Sang Jip Nam
, Hwan Myung Kim
, Juyoung Yoon

Department of Chemistry & Nanoscience

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

176 Scopus citations

Abstract

Hypochlorite (OCl^-) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl^- at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl^- recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl^- in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl^-, displayed a selective fluorescent off/on response to OCl^- with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl^- in live RAW 264.7 cells via two-photon microscopy.

Original language	English
Pages (from-to)	6615-6620
Number of pages	6
Journal	Analytical Chemistry
Volume	88
Issue number	12
DOIs	https://doi.org/10.1021/acs.analchem.6b01738
State	Published - 21 Jun 2016

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© 2016 American Chemical Society.

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title = "A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria",

abstract = "Hypochlorite (OCl-) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl- at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl- recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl- in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl-, displayed a selective fluorescent off/on response to OCl- with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl- in live RAW 264.7 cells via two-photon microscopy.",

author = "Qingling Xu and Heo, \{Cheol Ho\} and Kim, \{Jin A.\} and Lee, \{Hye Sue\} and Ying Hu and Dayoung Kim and Swamy, \{Kunemadihalli Mathada Kotraiah\} and Gyoungmi Kim and Nam, \{Sang Jip\} and Kim, \{Hwan Myung\} and Juyoung Yoon",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = jun,

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doi = "10.1021/acs.analchem.6b01738",

language = "English",

volume = "88",

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journal = "Analytical Chemistry",

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AU - Xu, Qingling

AU - Heo, Cheol Ho

AU - Kim, Jin A.

AU - Lee, Hye Sue

AU - Hu, Ying

AU - Kim, Dayoung

AU - Swamy, Kunemadihalli Mathada Kotraiah

AU - Kim, Gyoungmi

AU - Nam, Sang Jip

AU - Kim, Hwan Myung

AU - Yoon, Juyoung

PY - 2016/6/21

Y1 - 2016/6/21

N2 - Hypochlorite (OCl-) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl- at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl- recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl- in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl-, displayed a selective fluorescent off/on response to OCl- with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl- in live RAW 264.7 cells via two-photon microscopy.

AB - Hypochlorite (OCl-) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl- at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl- recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl- in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl-, displayed a selective fluorescent off/on response to OCl- with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl- in live RAW 264.7 cells via two-photon microscopy.

UR - https://www.scopus.com/pages/publications/84975865209

U2 - 10.1021/acs.analchem.6b01738

DO - 10.1021/acs.analchem.6b01738

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AN - SCOPUS:84975865209

SN - 0003-2700

VL - 88

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EP - 6620

JO - Analytical Chemistry

JF - Analytical Chemistry

IS - 12

ER -

A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria

Abstract

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