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

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

  • Spectrochim Acta A Mol Biomol Spectrosc. 2023 Mar 15:289:122193. doi: 10.1016/j.saa.2022.122193.
Małgorzata Świerczyńska 1,  Daniel Słowiński 1,  Radosław Michalski 2,  Jarosław Romański 3,  Radosław Podsiadły 1
Affiliations

Affiliations

  • 1 Institute of Polymer and Dye Technology, Faculty of Chemistry, Lodz University of Technology, Stefanowskiego 16, 90-537 Lodz, Poland.
  • 2 Institute of Applied Radiation Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90‑924 Lodz, Poland.
  • 3 Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.
PMID: 36508902 DOI: 10.1016/j.saa.2022.122193
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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