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DOI: 10.1055/s-0036-1591888
Development of a Ratiometric Fluorescent Probe with Two Reactive Sulfoxides for Monitoring the Activity of Methionine Sulfoxide Reductase A
This research was supported by the Czech Science Foundation (Grantová Agentura České Republiky, GACR 17-25897Y).Publication History
Received: 05 December 2017
Accepted after revision: 15 December 2017
Publication Date:
18 January 2018 (online)
![](https://www.thieme-connect.de/media/synthesis/201804/lookinside/thumbnails/ss-2017-z0786-op_10-1055_s-0036-1591888-1.jpg)
Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry
Abstract
Biological oxidation of methionine side chains in proteins is a process that affects the functions of many proteins. One of the key regulators of this signaling is the enzyme methionine sulfoxide reductase A (MsrA). MsrA is implicated in a number of diseases, but detailed understanding of its function is hindered by the lack of tools for monitoring the enzyme’s activity. We have designed and synthesized a probe named (S,S)-Sulfox-2 that is based on a BODIPY fluorophore and is equipped with two chiral sulfoxide units of defined stereochemistry. (S,S)-Sulfox-2 is shown to be highly responsive to MsrA and allows tracing of the MsrA activity by a significant change in the fluorescence profile.
Keywords
chirality - fluorescent probes - oxidoreductases - Suzuki–Miyaura coupling - redox chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591888.
- Supporting Information
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