An instantaneous near-infrared trimethyl lock based fluorescent probe for biothiols with a large Stokes shift.

Using trimethyl lock as a useful mean, a selective and sensitive fluorescent probe was developed for the detection of biothiols with an emission in near infrared spectral region (694 nm) and a large Stokes shift (129 nm). The inserted trimethyl lock between the fluorophore and the sensing group, 2, 4-dinitrobenzensulfonate, highly improved the response rate of this probe toward GSH because the unfavorable steric interactions between three methyl groups resulted in an extremely rapid intramolecular lactonization reaction to form a hydrocoumarin. This probe displayed an instantaneous response (within seconds) to GSH at a very low concentration in aqueous medium and the detection limit was as low as 2.5 nM based on S/N = 3. The fluorescence intensity of the solution of probe 1 at 694 nm displayed a good linearity (R = 0.9917) with the concentration of GSH in a range of 0.0-5.0 µM. Importantly, this probe exhibited a good performance in detecting biothiols in serum samples, living cells and organism.

A Triple-Emission Fluorescent Probe for Discriminatory Detection of Cysteine/Homocysteine, Glutathione/Hydrogen Sulfide, and Thiophenol in Living Cells.

Thiols, such as cysteine (Cys), homocysteine (Hcy), glutathione (GSH), hydrogen sulfide (H2S), and thiophenol are metabolically correlated with each other via redox reactions. As a result of the similarity of chemical properties between Cys, Hcy, GSH, H2S, and thiophenol, it is very challenging to develop an effective methodology to differentiate them. In this work, a triple-emission fluorescent probe, NCQ, was reported for the simultaneous detection of Cys/Hcy, GSH/H2S, and thiophenol with high sensitivity and selectivity. The solution of NCQ displayed distinct fluorescent signals toward Cys/Hcy, GSH/H2S, and thiophenol: blue and green for Cys/Hcy, blue for GSH/H2S, blue and red for thiophenol. Through the blue-green-red emission color combination, Cys/Hcy, GSH/H2S, and thiophenol could be discriminatively detected in solution and in living cells.

A red-emitting fluorescent probe for the detection of Hg2+ in aqueous medium, living cells and organisms with a large Stokes shift.

A red-emitting fluorescent probe has been developed for the selective and sensitive detection of Hg2+. With the addition of Hg2+, the solution of probe 1 displayed a remarkable fluorescence enhancement (102 fold) with λemmax = 625 nm and a large Stokes shift (150 nm). The detection limit of this probe was as low as 7.1 nM based on S/N = 3. This probe exhibited a good performance in detecting Hg2+ in real water samples, living cells and organisms.

Methylated chromenoquinoline dyes: synthesis, optical properties, and application for mitochondrial labeling.

Methylated chromenoquinoline dyes were designed and synthesized, and their photophysical properties were investigated. These new fluorescent dyes exhibited relatively high quantum yields, long wavelength emissions, large Stokes shifts, large absorption extinction coefficients and good water-solubility. Importantly, these methylated cation dyes showed a specific staining ability for mitochondria in living cells with low cytotoxicity.

A red-emitting fluorescent probe for hydrogen sulfide in living cells with a large Stokes shift.

A red-emitting fluorescent probe was developed for the sensitive and selective detection of H2S. Upon treatment with H2S, this probe exhibited a remarkable fluorescence enhancement (10 fold) with a large Stokes shift (125 nm). The detection limit of this probe was as low as 5.7 nM based on S/N = 3. The application of this probe in the detection of intracellular H2S in living cells is successfully demonstrated.

Ratiometric Fluorescent Probe for Lysosomal pH Measurement and Imaging in Living Cells Using Single-Wavelength Excitation.

A novel lysosome-targeting ratiometric fluorescent probe (CQ-Lyso) based on the chromenoquinoline chromorphore has been developed for the selective and sensitive detection of intracellular pH in living cells. In acidic media, the protonation of the quinoline ring of CQ-Lyso induces an enhanced intramolecular charge transfer (ICT) process, which results in large red-shifts in both the absorption (104 nm) and emission (53 nm) spectra which forms the basis of a new ratiometric fluorescence pH sensor. This probe efficiently stains lysosomes with high Pearson's colocalization coefficients using LysoTrackerDeep Red (0.97) and LysoTrackerBlue DND-22 (0.95) as references. Importantly, we show that CQ-Lyso quantitatively measures and images lysosomal pH values in a ratiometric manner using single-wavelength excitation.