Fluorescent Probe For Biothiols Research Articles

Structure modulation on fluorescent probes for biothiols and the reversible imaging of glutathione in living cells.

The detection of small molecular biothiols (cysteine, homocysteine and glutathione) is of great importance, as they involve in a series of physiological and pathological processes and are associated with many diseases. To realize the real-time monitoring of a specific biothiol, a rapid and reversible probe is required. Therefore, three probes, namely, o-MNPy, m-MNPy and p-MNPy, with pyridine substituted α, β-unsaturated ketone as the recognition site, were reported here, and the reactivity of the recognition site was finely tuned by the connection mode of the pyridine unit. To single out the optimal one, the response performances of three probes toward each biothiol were systemically studied, taking the differences of the intracellular contents of three biothiols into account during the evaluation. Biothiols reacted with the probes through Michael addition, and results showed that the slight structural variations could affect the performances of the probes obviously. p-MNPy with the pyridine unit connected to the recognition site through the para-position of the nitrogen atom, revealed the best sensing ability among the three probes. It demonstrated rapid response, good selectivity and sensitivity, excellent pH adaptability to Cys and GSH, and displayed reversible detection toward GSH. Finally, p-MNPy was successfully applied to track the GSH fluctuations under the oxidative stress stimulated by H2O2 in living cells.

Recent Advances in Fluorescent Probes for Biothiols

Recent Advances in Fluorescent Probes for Biothiols

BODIPY-Based Fluorescent Probes for Biothiols.

Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle-targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

Fluorescent probes for detection of biothiols based on “aromatic nucleophilic substitution-rearrangement” mechanism

Biothiols, including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play important roles in physiological processes, and the detection of thiol using fluorescent probes has attracted attention due to their high sensitivity and selectively and invasive on-time imaging. However, the similar structures and reactivity of these biothiols present great challenges for selective detection. This review focused on the the “aromatic nucleophilic substitution-rearrangement (SNAr-rearrangement) mechanism”, which provided a powerful tool to design fluorescent probes for the discrimination between biothiols. We classify the fluorescent probes according to types of fluorophores, such as difluoroboron dipyrromethene (BODIPY), nitrobenzoxadiazole (NBD), cyanine, pyronin, naphthalimide, coumarin, and so on. We hope this review will inspire exploration of new fluorescent probes for biothiols and other relevant analytes.

An “Off-On” Fluorescent Probe for Biothiols and Its Application in Bioimaging

An “Off-On” Fluorescent Probe for Biothiols and Its Application in Bioimaging

A Carbazole Based Bimodal "Turn-On" Fluorescent Probe for Biothiols (Cysteine/Homocysteine) and Fluoride: Sensing, Imaging and its Applications

A Carbazole Based Bimodal "Turn-On" Fluorescent Probe for Biothiols (Cysteine/Homocysteine) and Fluoride: Sensing, Imaging and its Applications

A low dose, highly selective and sensitive colorimetric and fluorescent probe for biothiols and its application in bioimaging.

A new colorimetric and fluorescent probe was reported, which can be used in a very low dosage (<20 nM) for rapid, highly selective and sensitive detection of biothiols.

Simultaneous Fluorescence Sensing of Cys and GSH from Different Emission Channels

A chlorinated coumarin-hemicyanine dye with three potential reaction sites was exploited as fluorescent probe for biothiols. The Cys-induced substitution-rearrangement-cyclization, Hcy-induced substitution-rearrangement, and GSH-induced substitution-cyclizatioin cascades lead to the corresponding amino-coumarin, amino-coumarin-hemicyanine, thiol-coumarin with distinct photophysical properties, enabling Cys and GSH to be selectively detected from different emission channels at two different excitation wavelengths.