Yuming Yang,†,§ Qiang Zhao,‡,§ Wei Feng,† and Fuyou Li*,† †Department of Chemistry and State Key Laboratory of Molecular Engineering of Polymers and Institutes of Biomedical Sciences, Fudan University, Shanghai 200433, P. R. China ‡Key Laboratory for Organic Electronics and Information Displays (KLOEID) and Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications, Nanjing 210046, P. R. China.

Luminescent chemodosimeters for bioimaging.

Design strategies for water-soluble small molecular chromogenic and fluorogenic probes.

Due to the biological importances of thiols, such as cysteine, homocysteine and glutathione, the development of optical probes for thiols has been an active research area in recent few years. This critical review focuses on the fluorescent or colorimetric sensors for thiols according to their unique mechanisms between sensors and thiols, including Michael addition, cyclization with aldehyde, cleavage of sulfonamide and sulfonate ester by thiols, cleavage of selenium–nitrogen bond by thiols, cleavage of disulfide by thiols, metal complexes-oxidation–reduction, metal complexes-displace coordination, nano-particles and others (110 references).

Fluorescent and colorimetric probes for detection of thiols

We report a novel design, based on a combination of lanthanide-doped upconversion nanoparticles and manganese dioxide nanosheets, for rapid, selective detection of glutathione in aqueous solutions and living cells. In this approach, manganese dioxide (MnO2) nanosheets formed on the surface of nanoparticles serve as an efficient quencher for upconverted luminescence. The luminescence can be turned on by introducing glutathione that reduces MnO2 into Mn2+. The ability to monitor the glutathione concentration intracellularly may enable rational design of a convenient platform for targeted drug and gene delivery.

Intracellular glutathione detection using MnO2-nanosheet-modified upconversion nanoparticles

We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol–halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.

BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine

Fast detection of cellular thiols in aqueous medium was achieved using a newly developed fluorescence probe (see picture). Based on this probe, a high-throughput fluorescence assay for glutathione reductase was developed.

Caihong Zhang

Papers

A Highly Sensitive Fluorescence Probe for Fast Thiol-Quantification Assay of Glutathione Reductase†