Synthesis 2018; 50(04): 772-777
DOI: 10.1055/s-0036-1591888
paper
© Georg Thieme Verlag Stuttgart · New York

Development of a Ratiometric Fluorescent Probe with Two ­Reactive Sulfoxides for Monitoring the Activity of Methionine Sulfoxide Reductase A

Nikolai Makukhin
Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 12843 Prague 2, Czech Republic   Email: misek@natur.cuni.cz
,
Vladimír Nosek
Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 12843 Prague 2, Czech Republic   Email: misek@natur.cuni.cz
,
Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 12843 Prague 2, Czech Republic   Email: misek@natur.cuni.cz
› Author Affiliations
This research was supported by the Czech Science Foundation (Grantová Agentura České Republiky, GACR 17-25897Y).
Further Information

Publication History

Received: 05 December 2017

Accepted after revision: 15 December 2017

Publication Date:
18 January 2018 (online)


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.

Supporting Information