Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 28, Pages 8433-8438Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902505
Keywords
aggregation-induced emissions; biological activity; biosensors; tetraphenylethene; thiols
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Funding
- Research Grants Council of Hong Kong [603008, 602706]
- University Grants committee of Hong Kong [AoE/P-03/08]
- National Science Foundation of China [20974028]
- Ministry of Science & Technology of China [2009CB623605]
- Cao Guangbiao Foundation of Zhejiang University
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A handy, specific, sensitive bioprobe has been developed. Tetraphenylethene (TPE) was functionalized by a maleimide (MI) group, giving a TPE-MI adduct that was nonemissive in both solution and the solid state. It was readily transformed into a fluorogen showing an aggregation-induced emission (AIE) property by the click addition of thiol to its MI pendant. The click reaction and the AIE effect enabled TPE-MI to function as a thiol-specific bioprobe in the solid state. Thus, the spot of TPE-MI on a TLC plate became emissive when it had been exposed to L-cysteine, an amino acid containing a thiol group, but remained nonemissive when exposed to other amino acids that lack free thiol units. The thiol-activated emission was rapid and strong, readily detected by the naked eye at an analyte concentration as low as approximately 1 ppb, thanks to the lighting up nature of the bio-probing process. Similarly, the emission of TPE-MI was turned on only by the proteins containing free thiol units, such as glutathione. Clear fluorescence images were taken when living cells were stained by using TPE-MI as a visualization agent, affording a facile fluorescent maker for mapping the distribution of thiol species in cellular systems.
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