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. 2023 Mar 15:289:122193.
doi: 10.1016/j.saa.2022.122193. Epub 2022 Dec 5.

A thiomorpholine-based fluorescent probe for the far-red hypochlorous acid monitoring

Małgorzata Świerczyńska  1 , Daniel Słowiński  1 , Radosław Michalski  2 , Jarosław Romański  3 , Radosław Podsiadły  1
Affiliations

A thiomorpholine-based fluorescent probe for the far-red hypochlorous acid monitoring

Małgorzata Świerczyńska et al. Spectrochim Acta A Mol Biomol Spectrosc. .

Abstract

A simple thiomorpholine-based fluorescent probe was designed and synthesized by combining thiomorpholine (TM) and nitrobenzenoselenadiazoles fluorophore (NBD-Se). The thiomorpholine group quenches the fluorescence of NBD-Se efficiently through the photoinduced electron transfer (PET) effect. Hypochlorous acid (HOCl) oxidizes the NBD-Se-TM probe to its fluorescent S-oxide (NBD-Se-TSO) with a 1:1 stoichiometry. The desirable features of NBD-Se-TM for detecting HOCl in aqueous solutions, such as its high sensitivity and selectivity, reliability at physiological pH, and rapid fluorescence response, enabled its application in the detection of HOCl produced by myeloperoxidase. The results proved that NBD-Se-TM is a promising fluorescent probe that can be used in screening assays for MPO inhibitors. Its high reaction rate constant with HOCl (2k = 2.0 × 107M-1s-1) indicates the possibility of application in more complex biological systems.

Keywords: Fluorescent selenium-containing probe; Hypochlorous acid; Myeloperoxidase; Stoichiometric reaction; Thiomorpholine-based probes.

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Conflict of interest statement

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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