Design strategies of fluorescent probes for selective detection among biothiols

Abstract

Simple thiol derivatives, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play key roles in biological processes, and the fluorescent probes to detect such thiols in vivo selectively with high sensitivity and fast response times are critical for understanding their numerous functions. However, the similar structures and reactivities of these thiols pose considerable challenges to the development of such probes. This review focuses on various strategies for the design of fluorescent probes for the selective detection of biothiols. We classify the fluorescent probes for discrimination among biothiols according to reaction types between the probes and thiols such as cyclization with aldehydes, conjugate addition-cyclization with acrylates, native chemical ligation, and aromatic substitution-rearrangement.

Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

“…[17] Various analytical methods have been established to detect GSH, including high-performance liquid chromatography, [18] electrochemical assays [19] and fluorescence spectrometry. [20] Compared with other detection methods, the fluorescent methods are the most practical tools for imaging GSH in living cells, due to the high sensitivity, easy implementation, real-time imaging and non-invasiveness. [21][22][23][24] Due to the thiol's unique properties of high nucleophilicity and strong binding affinity to metal ions, various fluorescent probes for GSH have been developed based on different mechanisms including Michael addition reactions, [25] cleavage reactions of 2,4-dinitrobenzenesulfonyl (DNBS) with thiols [26][27] and the nucleophilic substitution reaction.…”

Photoluminescent Metal–Organic Frameworks for Gas Sensing

“…Because liquids are closely related to the surrounding environment and human body, many materials (including MOFs) have been developed for liquid‐phase luminescence sensing of ionic and molecular species 46, 47, 48, 49, 50, 51, 52, 53. In the liquid environment, the types and concentrations of the analytes can be easily controlled for quantitative detection (calibration).…”

A multi-emissive fluorescent probe for the discrimination of glutathione and cysteine

“…Great efforts have been devoted to develop reaction based fluorescent sensors for the detection of thiols in living systems (Niu et al, 2015a;Jung et al, 2013;Wang et al, 2014b). Most of the sensors were able to distinguish biothiols from other amino acids by taking advantage of the strong nucleophilic ability of thiols (Chen et al, 2010).…”

“…Lately, considerable efforts have been made to develop fluorescent sensors with selective response to Cys, Hcy, or GSH (Niu et al, 2015a). For instance, the selective detections of Cys/Hcy were usually performed based on the strategy of cyclization with aldehydes (Rusin et al, 2004;Wang et al, 2012;Barve et al, 2014) and conjugate addition-cyclization with acrylates (Yang et al, 2011;Niu et al, 2016;Han et al, 2015;Guo et al, 2012).…”