A chloroacetate-caged fluorescein chemodosimeter for imaging cysteine/homocysteine in living cells

Baocun Zhu; Yunzhou Zhao; Qi Zhou; Bing Zhang; Lunying Liu; Bin Du; Xiaoling Zhang

doi:10.1002/ejoc.201201407

A chloroacetate-caged fluorescein chemodosimeter for imaging cysteine/homocysteine in living cells

Baocun Zhu^*, Yunzhou Zhao, Qi Zhou, Bing Zhang, Lunying Liu, Bin Du, Xiaoling Zhang

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

University of Jinan

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

29 Citations (Scopus)

Abstract

A chloroacetate-caged fluorescein chemodosimeter (CACFC) employing a double molecular recognition mechanism was designed and synthesized to selectively detect cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The results showed that CACFC could serve as a "naked- eye" indicator, and quantitatively detect Cys and Hcy with a detection limit of 4 μM (Cys) and 7 μM (Hcy). Additionally, CACFC was successfully applied to the fluorescence imaging of Cys and Hcy in living cells. The mechanism of the reaction between CACFC and Cys/Hcy was confirmed by ESI-MS and fluorescence spectroscopic analysis to involve a conjugate substitution/ cyclization sequence. We highlight the simplicity of the design and synthesis and show that its combined properties, such as high specificity, high sensitivity, fast response, quantitative detection and real time Cys and Hcy imaging in living cells should find applications in imaging and biomedical fields.

Original language	English
Pages (from-to)	888-893
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	5
DOIs	https://doi.org/10.1002/ejoc.201201407
Publication status	Published - Feb 2013

Keywords

Amino acids
Dyes/Pigments
Imaging agents
Molecular recognition
Sensors

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abstract = "A chloroacetate-caged fluorescein chemodosimeter (CACFC) employing a double molecular recognition mechanism was designed and synthesized to selectively detect cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The results showed that CACFC could serve as a {"}naked- eye{"} indicator, and quantitatively detect Cys and Hcy with a detection limit of 4 μM (Cys) and 7 μM (Hcy). Additionally, CACFC was successfully applied to the fluorescence imaging of Cys and Hcy in living cells. The mechanism of the reaction between CACFC and Cys/Hcy was confirmed by ESI-MS and fluorescence spectroscopic analysis to involve a conjugate substitution/ cyclization sequence. We highlight the simplicity of the design and synthesis and show that its combined properties, such as high specificity, high sensitivity, fast response, quantitative detection and real time Cys and Hcy imaging in living cells should find applications in imaging and biomedical fields.",

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AU - Zhu, Baocun

AU - Zhao, Yunzhou

AU - Zhou, Qi

AU - Zhang, Bing

AU - Liu, Lunying

AU - Du, Bin

AU - Zhang, Xiaoling

PY - 2013/2

Y1 - 2013/2

N2 - A chloroacetate-caged fluorescein chemodosimeter (CACFC) employing a double molecular recognition mechanism was designed and synthesized to selectively detect cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The results showed that CACFC could serve as a "naked- eye" indicator, and quantitatively detect Cys and Hcy with a detection limit of 4 μM (Cys) and 7 μM (Hcy). Additionally, CACFC was successfully applied to the fluorescence imaging of Cys and Hcy in living cells. The mechanism of the reaction between CACFC and Cys/Hcy was confirmed by ESI-MS and fluorescence spectroscopic analysis to involve a conjugate substitution/ cyclization sequence. We highlight the simplicity of the design and synthesis and show that its combined properties, such as high specificity, high sensitivity, fast response, quantitative detection and real time Cys and Hcy imaging in living cells should find applications in imaging and biomedical fields.

AB - A chloroacetate-caged fluorescein chemodosimeter (CACFC) employing a double molecular recognition mechanism was designed and synthesized to selectively detect cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The results showed that CACFC could serve as a "naked- eye" indicator, and quantitatively detect Cys and Hcy with a detection limit of 4 μM (Cys) and 7 μM (Hcy). Additionally, CACFC was successfully applied to the fluorescence imaging of Cys and Hcy in living cells. The mechanism of the reaction between CACFC and Cys/Hcy was confirmed by ESI-MS and fluorescence spectroscopic analysis to involve a conjugate substitution/ cyclization sequence. We highlight the simplicity of the design and synthesis and show that its combined properties, such as high specificity, high sensitivity, fast response, quantitative detection and real time Cys and Hcy imaging in living cells should find applications in imaging and biomedical fields.

KW - Amino acids

KW - Dyes/Pigments

KW - Imaging agents

KW - Molecular recognition

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A chloroacetate-caged fluorescein chemodosimeter for imaging cysteine/homocysteine in living cells

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Keywords

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