Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine

Chae Yeong Kim; Hyo Jin Kang; Sang J. Chung; Hyun Kyung Kim; Sang Yun Na; Hae Jo Kim

doi:10.1021/acs.analchem.6b01346

Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine

Chae Yeong Kim, Hyo Jin Kang, Sang J. Chung, Hyun Kyung Kim, Sang Yun Na, Hae Jo Kim

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

74 Scopus citations

Abstract

We report a chromogenic and fluorescence turn-on probe based on crotonoyl ester-functionalized oxazolidinoindole for the selective detection of cysteine in neutral buffer. The probe rapidly formed indocyanophenolate through the Michael addition and a subsequent cyclization reaction of cysteine, inducing both a dramatic bathochromic shift (>130 nm) and a large fluorescence turn-on response (F/F₀ 12) in the UV-vis and fluorescence spectra and affording a micromolar limit of detection (LOD = 5.0 μM) of cysteine in HEPES buffer. When cysteine was added, the probe exhibited a dual optical change with strong green fluorescence and dramatic red color by the oxazolidinoindole-to-hydroxyethylindolium transformation. Further cellular application of the probe was successfully performed for the mitochondrial imaging of HeLa cells.

Original language	English
Pages (from-to)	7178-7182
Number of pages	5
Journal	Analytical Chemistry
Volume	88
Issue number	14
DOIs	https://doi.org/10.1021/acs.analchem.6b01346
State	Published - 19 Jul 2016
Externally published	Yes

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title = "Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine",

abstract = "We report a chromogenic and fluorescence turn-on probe based on crotonoyl ester-functionalized oxazolidinoindole for the selective detection of cysteine in neutral buffer. The probe rapidly formed indocyanophenolate through the Michael addition and a subsequent cyclization reaction of cysteine, inducing both a dramatic bathochromic shift (>130 nm) and a large fluorescence turn-on response (F/F0 12) in the UV-vis and fluorescence spectra and affording a micromolar limit of detection (LOD = 5.0 μM) of cysteine in HEPES buffer. When cysteine was added, the probe exhibited a dual optical change with strong green fluorescence and dramatic red color by the oxazolidinoindole-to-hydroxyethylindolium transformation. Further cellular application of the probe was successfully performed for the mitochondrial imaging of HeLa cells.",

author = "Kim, \{Chae Yeong\} and Kang, \{Hyo Jin\} and Chung, \{Sang J.\} and Kim, \{Hyun Kyung\} and Na, \{Sang Yun\} and Kim, \{Hae Jo\}",

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

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doi = "10.1021/acs.analchem.6b01346",

language = "English",

volume = "88",

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T1 - Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine

AU - Kim, Chae Yeong

AU - Kang, Hyo Jin

AU - Chung, Sang J.

AU - Kim, Hyun Kyung

AU - Na, Sang Yun

AU - Kim, Hae Jo

PY - 2016/7/19

Y1 - 2016/7/19

N2 - We report a chromogenic and fluorescence turn-on probe based on crotonoyl ester-functionalized oxazolidinoindole for the selective detection of cysteine in neutral buffer. The probe rapidly formed indocyanophenolate through the Michael addition and a subsequent cyclization reaction of cysteine, inducing both a dramatic bathochromic shift (>130 nm) and a large fluorescence turn-on response (F/F0 12) in the UV-vis and fluorescence spectra and affording a micromolar limit of detection (LOD = 5.0 μM) of cysteine in HEPES buffer. When cysteine was added, the probe exhibited a dual optical change with strong green fluorescence and dramatic red color by the oxazolidinoindole-to-hydroxyethylindolium transformation. Further cellular application of the probe was successfully performed for the mitochondrial imaging of HeLa cells.

AB - We report a chromogenic and fluorescence turn-on probe based on crotonoyl ester-functionalized oxazolidinoindole for the selective detection of cysteine in neutral buffer. The probe rapidly formed indocyanophenolate through the Michael addition and a subsequent cyclization reaction of cysteine, inducing both a dramatic bathochromic shift (>130 nm) and a large fluorescence turn-on response (F/F0 12) in the UV-vis and fluorescence spectra and affording a micromolar limit of detection (LOD = 5.0 μM) of cysteine in HEPES buffer. When cysteine was added, the probe exhibited a dual optical change with strong green fluorescence and dramatic red color by the oxazolidinoindole-to-hydroxyethylindolium transformation. Further cellular application of the probe was successfully performed for the mitochondrial imaging of HeLa cells.

UR - https://www.scopus.com/pages/publications/84978833970

U2 - 10.1021/acs.analchem.6b01346

DO - 10.1021/acs.analchem.6b01346

M3 - Article

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AN - SCOPUS:84978833970

SN - 0003-2700

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JO - Analytical Chemistry

JF - Analytical Chemistry

IS - 14

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Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine

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