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A Chloroacetate‐Caged Fluorescein Chemodosimeter for Imaging Cysteine/Homocysteine in Living Cells
Author(s) -
Zhu Baocun,
Zhao Yunzhou,
Zhou Qi,
Zhang Bing,
Liu Lunying,
Du Bin,
Zhang Xiaoling
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201407
Subject(s) - chemistry , cysteine , glutathione , homocysteine , fluorescein , fluorescence , conjugate , detection limit , naked eye , amino acid , combinatorial chemistry , photochemistry , biochemistry , chromatography , enzyme , mathematical analysis , physics , mathematics , quantum mechanics
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 μ M (Cys) and 7 μ M (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.