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

168 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",

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

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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

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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.

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JF - Analytical Chemistry

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

Abstract

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