Simple biosensor with high selectivity and sensitivity: thiol-specific biomolecular probing and intracellular imaging by AIE fluorogen on a TLC plate through a thiol-ene click mechanism

Chemistry. 2010 Jul 26;16(28):8433-8. doi: 10.1002/chem.200902505.

Abstract

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 bioprobing 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biosensing Techniques
  • Chromatography, Thin Layer
  • Coloring Agents / chemistry*
  • Diagnostic Imaging / methods
  • Ethylenes / chemistry*
  • Fluorescence
  • Maleimides / chemistry*
  • Molecular Structure
  • Staining and Labeling / methods
  • Sulfhydryl Compounds / chemistry*

Substances

  • Coloring Agents
  • Ethylenes
  • Maleimides
  • Sulfhydryl Compounds
  • maleimide