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Review
. 2017 Oct 16;56(43):13188-13198.
doi: 10.1002/anie.201704084. Epub 2017 Sep 22.

Fluorescent Probes with Multiple Binding Sites for the Discrimination of Cys, Hcy, and GSH

Cai-Xia Yin  1 , Kang-Ming Xiong  1 , Fang-Jun Huo  2 , James C Salamanca  3 , Robert M Strongin  3
Affiliations
Review

Fluorescent Probes with Multiple Binding Sites for the Discrimination of Cys, Hcy, and GSH

Cai-Xia Yin et al. Angew Chem Int Ed Engl. .

Abstract

Biothiols such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in maintaining redox homeostasis in biological systems. This Minireview summarizes the most significant current challenges in the field of thiol-reactive probes for biomedical research and diagnostics, emphasizing the needs and opportunities that have been under-investigated by chemists in the selective probe and sensor field. Progress on multiple binding site probes to distinguish Cys, Hcy, and GSH is highlighted as a creative new direction in the field that can enable simultaneous, accurate ratiometric monitoring. New probe design strategies and researcher priorities can better help address current challenges, including the monitoring of disease states such as autism and chronic diseases involving oxidative stress that are characterized by divergent levels of GSH, Cys, and Hcy.

Keywords: biothiols; detection methods; fluorescence; imaging; multiple-binding-site probes.

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Conflict of interest statement

Conflict of interest

The authors declare no conflict of interest.

Figures

Figure 1.
Figure 1.
The major amino thiols.
Figure 2.
Figure 2.
Significant derivatives of Hey include its thiolactone form (HTL), which reacts with Lys residues to form post-translational modifications. The Hcy-Lys isopeptide results from protein degradation. HTL, N-Hcy-protein, and Nε-Hcy-Lys each have shown evidence of significant health impact. However, there is a lack of selective abiotic optical indicators dyes and probes that have targeted these analytes. Their physiological and structural relationships render them intriguing targets for multiple binding site probes.
Figure 3.
Figure 3.
The reactions of 1 with Cys, Hcy, and GSH.
Figure 4.
Figure 4.
The reactions of 2 with Cys, Hcy, and GSH.
Figure 5.
Figure 5.
The reactions of 3 with Cys, Hey, and GSH.
Figure 6.
Figure 6.
The reactions of 4 with Cys, Hcy, and GSH.
Figure 7.
Figure 7.
The reactions of 5 with Cys, Hcy, and GSH.
See this image and copyright information in PMC

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