A cysteine-selective fluorescent probe for the cellular detection of cysteine

Hyo Sung Jung; Ji Hye Han; Tuhin Pradhan; Sooyeon Kim; Seok Won Lee; Jonathan L. Sessler; Tae Woo Kim; Chulhun Kang; Jong Seung Kim

doi:10.1016/j.biomaterials.2011.10.040

A cysteine-selective fluorescent probe for the cellular detection of cysteine

Hyo Sung Jung, Ji Hye Han, Tuhin Pradhan, Sooyeon Kim, Seok Won Lee, Jonathan L. Sessler, Tae Woo Kim, Chulhun Kang, Jong Seung Kim

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

206 Citations (Scopus)

Abstract

A series of coumarin fluorophores (1-3), each bearing a double bond conjugated quinoline unit that can undergo a Michael-type reaction with thiol-containing compounds, is reported. These systems, designed to provide so-called turn-on changes in fluorescence response when exposed to thiols, act as fluorescent chemical sensors for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). In the case of 1, selectivity for Cys over Hcy and GSH is observed, both in terms of analyte-induced signal enhancement and response time. On the basis of fluorescence spectroscopic analyses, DFT calculations, and pH dependent studies this substrate selectivity is ascribed to steric interactions between the substituents on the quinolone units present in 1 and the targeted thiols, as well as to the comparatively lower pK _a value of Cys relative to Hcy and GSH. In aqueous solution, probe 1 was found capable of detecting Cys with a detection limit of 10 ^-7 m. This system was successfully applied to the fluorescence imaging of intracellular Cys in HepG2 cells.

Original language	English
Pages (from-to)	945-953
Number of pages	9
Journal	Biomaterials
Volume	33
Issue number	3
DOIs	https://doi.org/10.1016/j.biomaterials.2011.10.040
Publication status	Published - 2012 Jan

Bibliographical note

Funding Information:
This work was supported by the CRI program ( 2011-0000420 ) from the National Research Foundation of Korea. Support from the U.S. NIH (grant GM 58907 to J.L.S.) and the Robert A. Welch Foundation (grant F-1018 to J.L.S.) are also acknowledged.

Keywords

Cellular detection
Cysteine
DFT calculations
Fluorescence
Thiol

ASJC Scopus subject areas

Mechanics of Materials
Ceramics and Composites
Bioengineering
Biophysics
Biomaterials

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10.1016/j.biomaterials.2011.10.040

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title = "A cysteine-selective fluorescent probe for the cellular detection of cysteine",

abstract = "A series of coumarin fluorophores (1-3), each bearing a double bond conjugated quinoline unit that can undergo a Michael-type reaction with thiol-containing compounds, is reported. These systems, designed to provide so-called turn-on changes in fluorescence response when exposed to thiols, act as fluorescent chemical sensors for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). In the case of 1, selectivity for Cys over Hcy and GSH is observed, both in terms of analyte-induced signal enhancement and response time. On the basis of fluorescence spectroscopic analyses, DFT calculations, and pH dependent studies this substrate selectivity is ascribed to steric interactions between the substituents on the quinolone units present in 1 and the targeted thiols, as well as to the comparatively lower pK a value of Cys relative to Hcy and GSH. In aqueous solution, probe 1 was found capable of detecting Cys with a detection limit of 10 -7 m. This system was successfully applied to the fluorescence imaging of intracellular Cys in HepG2 cells.",

keywords = "Cellular detection, Cysteine, DFT calculations, Fluorescence, Thiol",

author = "Jung, {Hyo Sung} and Han, {Ji Hye} and Tuhin Pradhan and Sooyeon Kim and Lee, {Seok Won} and Sessler, {Jonathan L.} and Kim, {Tae Woo} and Chulhun Kang and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the CRI program ( 2011-0000420 ) from the National Research Foundation of Korea. Support from the U.S. NIH (grant GM 58907 to J.L.S.) and the Robert A. Welch Foundation (grant F-1018 to J.L.S.) are also acknowledged. ",

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journal = "Biomaterials",

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AU - Jung, Hyo Sung

AU - Han, Ji Hye

AU - Pradhan, Tuhin

AU - Kim, Sooyeon

AU - Lee, Seok Won

AU - Sessler, Jonathan L.

AU - Kim, Tae Woo

AU - Kang, Chulhun

AU - Kim, Jong Seung

N1 - Funding Information: This work was supported by the CRI program ( 2011-0000420 ) from the National Research Foundation of Korea. Support from the U.S. NIH (grant GM 58907 to J.L.S.) and the Robert A. Welch Foundation (grant F-1018 to J.L.S.) are also acknowledged.

PY - 2012/1

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N2 - A series of coumarin fluorophores (1-3), each bearing a double bond conjugated quinoline unit that can undergo a Michael-type reaction with thiol-containing compounds, is reported. These systems, designed to provide so-called turn-on changes in fluorescence response when exposed to thiols, act as fluorescent chemical sensors for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). In the case of 1, selectivity for Cys over Hcy and GSH is observed, both in terms of analyte-induced signal enhancement and response time. On the basis of fluorescence spectroscopic analyses, DFT calculations, and pH dependent studies this substrate selectivity is ascribed to steric interactions between the substituents on the quinolone units present in 1 and the targeted thiols, as well as to the comparatively lower pK a value of Cys relative to Hcy and GSH. In aqueous solution, probe 1 was found capable of detecting Cys with a detection limit of 10 -7 m. This system was successfully applied to the fluorescence imaging of intracellular Cys in HepG2 cells.

AB - A series of coumarin fluorophores (1-3), each bearing a double bond conjugated quinoline unit that can undergo a Michael-type reaction with thiol-containing compounds, is reported. These systems, designed to provide so-called turn-on changes in fluorescence response when exposed to thiols, act as fluorescent chemical sensors for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). In the case of 1, selectivity for Cys over Hcy and GSH is observed, both in terms of analyte-induced signal enhancement and response time. On the basis of fluorescence spectroscopic analyses, DFT calculations, and pH dependent studies this substrate selectivity is ascribed to steric interactions between the substituents on the quinolone units present in 1 and the targeted thiols, as well as to the comparatively lower pK a value of Cys relative to Hcy and GSH. In aqueous solution, probe 1 was found capable of detecting Cys with a detection limit of 10 -7 m. This system was successfully applied to the fluorescence imaging of intracellular Cys in HepG2 cells.

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A cysteine-selective fluorescent probe for the cellular detection of cysteine

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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