Quinolone-based fluorescent probes for distinguished detection of Cys and GSH through different fluorescence channels

Biothiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play different crucial roles in maintaining redox homeostasis in biological systems. Owing to their similar structures and reactivity, they present great challenges for their distinguished detection. In this work, we have c...

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Bibliographic Details
Published inNew journal of chemistry Vol. 44; no. 32; pp. 13781 - 13787
Main Authors Fu, Ying-Long, Chen, Xiang-Gen, Li, Hao, Feng, Wei, Song, Qin-Hua
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.08.2020
Royal Society of Chemistry
Subjects
Channels
Chemistry
Chemistry, Multidisciplinary
Coumarin
Fluorescent indicators
Glutathione
Homeostasis
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
Selectivity
Spectra
Spectral sensitivity
Thiols
Toxicity
HOMOCYSTEINE
NAPHTHALIMIDE
DESIGN
GLUTATHIONE
DISCRIMINATION
QUANTIFICATION
CYSTEINE
SENSOR
SELECTIVE DETECTION
LIVING CELLS
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Summary:Biothiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play different crucial roles in maintaining redox homeostasis in biological systems. Owing to their similar structures and reactivity, they present great challenges for their distinguished detection. In this work, we have constructed three different types of quinolone-based fluorescent probes ( QB-1 , QB-2 and QB-3 ) for the detection of biothiols. Among them QB-3 , a red fluorescent probe, displays the best sensing performance such as high selectivity and good sensitivity for Cys (LOD = 0.17 μM) and GSH (LOD = 0.46 μM), and it can distinguish between Cys, GSH and Hcy through two different fluorescence channels; specifically, a turn-on fluorescence centred at 420 nm for Cys, ratiometric fluorescence at 643 nm/537 nm for GSH and no response for Hcy. Furthermore, QB-3 has been successfully applied for the simultaneous detection of endogenous Cys and GSH in living cells. Dual-channel discrimination of Cys and GSH using a red fluorescent probe.
Bibliography:QB-1
toward thiols, spectral response of
QB-3
QB-2
10.1039/d0nj03274c
and
toward NAC, evidence of the sensing products for
Electronic supplementary information (ESI) available: Summary of chlorinated coumarin derivative fluorescent probes for distinguishing biothiols with multiple sets of fluorescence signals, spectral response of
with Cys/Hcy/GSH, the selectivity of
pH effects and cytotoxicity, and copies of NMR spectra for compounds. See DOI
for ions, competitive reaction between two biothiols (Cys/GSH) with
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj03274c