Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 4, Pages 1311-1319Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203137
Keywords
bioimaging; biothiols; IR spectroscopy; phosphorescence; sensors
Categories
Funding
- National Natural Science Foundation of China [61177029, 21174064, 21171098]
- National Basic Research Program of China (973 Program) [2009CB930601, 2012CB933300]
- Ministry of Education of China [IRT1148]
- Natural Science Fund for Colleges and Universities in Jiangsu Province [10KJB430010]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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Biothiols, such as cysteine (Cys) and homocysteine (Hcy), play very crucial roles in biological systems. Abnormal levels of these biothiols are often associated with many types of diseases. Therefore, the detection of Cys (or Hcy) is of great importance. In this work, we have synthesized an excellent OFF-ON phosphorescent chemodosimeter 1 for sensing Cys and Hcy with high selectivity and naked-eye detection based on an IrIII complex containing a 2,4-dinitrobenzenesulfonyl (DNBS) group within its ligand. The OFF-ON phosphorescent response can be assigned to the electron-transfer process from IrIII center and C boolean AND N ligands to the DNBS group as the strong electron-acceptor, which can quench the phosphorescence of probe 1 completely. The DNBS group can be cleaved by thiols of Cys or Hcy, and both the 3MLCT and 3LC states are responsible for the excited-state properties of the reaction product of probe 1 and Cys (or Hcy). Thus, the phosphorescence is switched on. Based on these results, a general principle for designing OFF-ON phosphorescent chemodosimeters based on heavy-metal complexes has been provided. Importantly, utilizing the long emission-lifetime of phosphorescence signal, the time-resolved luminescent assay of 1 in sensing Cys was realized successfully, which can eliminate the interference from the short-lived background fluorescence and improve the signal-to-noise ratio. As far as we know, this is the first report about the time-resolved luminescent detection of biothiols. Finally, probe 1 has been used successfully for bioimaging the changes of Cys/Hcy concentration in living cells.
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