一种基于噻咯啉的荧光探针，用于远红次氯酸的监测。

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

机构信息

Institute of Polymer and Dye Technology, Faculty of Chemistry, Lodz University of Technology, Stefanowskiego 16, 90-537 Lodz, Poland.

Institute of Applied Radiation Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90‑924 Lodz, Poland.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Mar 15;289:122193. doi: 10.1016/j.saa.2022.122193. Epub 2022 Dec 5.

DOI:10.1016/j.saa.2022.122193

PMID:36508902

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 (k = 2.0 × 10Ms) indicates the possibility of application in more complex biological systems.

摘要

设计并合成了一种基于噻唑烷的荧光探针，该探针通过将噻唑烷（TM）和硝基苯并硒二唑荧光团（NBD-Se）结合在一起。噻唑烷基团通过光诱导电子转移（PET）效应有效地猝灭 NBD-Se 的荧光。次氯酸（HOCl）将 NBD-Se-TM 探针氧化为其荧光 S-氧化物（NBD-Se-TSO），其化学计量比为 1:1。NBD-Se-TM 具有在水溶液中检测 HOCl 的理想特性，如高灵敏度和选择性、在生理 pH 值下的可靠性以及快速的荧光响应，使其能够应用于检测髓过氧化物酶产生的 HOCl。结果证明，NBD-Se-TM 是一种很有前途的荧光探针，可用于 MPO 抑制剂的筛选测定。它与 HOCl 的高反应速率常数（k = 2.0×10^4 M^-1 s^-1）表明它有可能应用于更复杂的生物系统。