Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 5, Pages 888-893Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201407
Keywords
Sensors; Imaging agents; Molecular recognition; Amino acids; Dyes; Pigments
Categories
Funding
- National Natural Science Foundation of China (NSFC) [21107029, 21175057, 21075052, 20975012]
- National Major Projects on Water Pollution Control and Management Technology [2008ZX07422]
- Scientific Research Foundation for Doctors of University of Jinan [XBS1039, XKY1046]
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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 mu M (Cys) and 7 mu 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.
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