Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application

In this work, tetrahydro-acridine salt hybrid coumarin dyes was designed and developed as a Near-infrared (NIR) fluorescent probe CM for the detection and fluorescent bioimaging of Cys/Hcy. The activated chlorine atom in probe facilitates more efficient nucleophilic substitution reaction, resulting...

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Veröffentlicht in:Sensors and actuators. B, Chemical Chemical, 2023-01, Vol.374, p.132799, Article 132799
Hauptverfasser: An, Shixuan, Lin, Yanfei, Wang, Jianbo, Ye, Tianqing, Mao, Yanyun, Zhang, Jian, Guo, Longhua, Li, Lei, Qian, Zhaosheng, Liu, Haiying
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container_title Sensors and actuators. B, Chemical
container_volume 374
creator An, Shixuan
Lin, Yanfei
Wang, Jianbo
Ye, Tianqing
Mao, Yanyun
Zhang, Jian
Guo, Longhua
Li, Lei
Qian, Zhaosheng
Liu, Haiying
description In this work, tetrahydro-acridine salt hybrid coumarin dyes was designed and developed as a Near-infrared (NIR) fluorescent probe CM for the detection and fluorescent bioimaging of Cys/Hcy. The activated chlorine atom in probe facilitates more efficient nucleophilic substitution reaction, resulting in fast responsive time (3 min toward 3 eq. Cys) and high sensitivity toward Cys with detection limit of 46 nM. More importantly, probe displays “Turn-on” near-infrared fluorescence emission (Emmax: 674 nm) with Large Strokes shift (about 200 nm) toward Cys/Hcy. Furthermore, probe could be used as efficient tool for imaging and detection of Cys/Hcy in mitochondria of living cells and in vivo. This work innovatively proposed a new design strategy for NIR fluorescent probe platform for the detection and fluorescence imaging of bio-thiols. [Display omitted] •A new tetrahydro-acridine salt hybrid coumarin dyes is designed as NIR fluorescent probe CM for detection of Cys/Hcy.•Probe shows remarkable “turn-on” NIR fluorescence change with Large Strokes shift, fast responsive time, high sensitivity and selectivity toward Cys/Hcy.•Probe display low cytotoxicity and mitochondria-targeting ability and can be used to visualize monitor Cys/Hcy changes in living cells and in vivo.
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[Display omitted] •A new tetrahydro-acridine salt hybrid coumarin dyes is designed as NIR fluorescent probe CM for detection of Cys/Hcy.•Probe shows remarkable “turn-on” NIR fluorescence change with Large Strokes shift, fast responsive time, high sensitivity and selectivity toward Cys/Hcy.•Probe display low cytotoxicity and mitochondria-targeting ability and can be used to visualize monitor Cys/Hcy changes in living cells and in vivo.</description><identifier>ISSN: 0925-4005</identifier><identifier>EISSN: 1873-3077</identifier><identifier>DOI: 10.1016/j.snb.2022.132799</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>Chlorine ; Coumarin ; Fluorescent indicators ; Large Stokes shift ; Medical imaging ; Mitochondria ; Mitochondria-targeted ; Near infrared radiation ; Near-infrared ; Substitution reactions ; Thiols ; Thiols florescent probe</subject><ispartof>Sensors and actuators. 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source ScienceDirect Journals (5 years ago - present)
subjects Chlorine
Coumarin
Fluorescent indicators
Large Stokes shift
Medical imaging
Mitochondria
Mitochondria-targeted
Near infrared radiation
Near-infrared
Substitution reactions
Thiols
Thiols florescent probe
title Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application
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