Fluorescent and colorimetric probes for detection of thiols

Chen, Xiaoqiang; Zhou, Ying; Peng, Xiaojun; Yoon, Juyoung

doi:10.1039/b925092a

Cited by 1,506 publications

(739 citation statements)

References 108 publications

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“…2,3 However, they are easily photobleached and often have narrow absorption and broad emission spectra with long tailing, which results in low detection sensitivity. 4,5 Thus, semiconductor quantum dots (QDs) (e.g., CdSe, CdTe) have received increasing attention, because of their good photostability, bright photoluminescence, narrow emission and broad excitation, high quantum yields, and large Stokes shift. 5−8 Based on the changes of fluorescence spectra, such QD labels have been widely used to detect various species such as ions, small organic molecules, and biomacromolecules.…”

Section: Introductionmentioning

confidence: 99%

Quantum Dots Based Mesoporous Structured Imprinting Microspheres for the Sensitive Fluorescent Detection of Phycocyanin

Zhong

Wang

et al. 2015

ACS Appl. Mater. Interfaces

138

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Phycocyanin with important physiological/environmental significance has attracted increasing attention; versatile molecularly imprinted polymers (MIPs) have been applied to diverse species, but protein imprinting is still quite difficult. Herein, using phycocyanin as template via a sol−gel process, we developed a novel fluorescent probe for specific recognition and sensitive detection of phycocyanin by quantum dots (QDs) based mesoporous structured imprinting microspheres (SiO 2 @QDs@ms-MIPs), obeying electron-transfer-induced fluorescence quenching mechanism. When phycocyanin was present, a Meisenheimer complex would be produced between phycocyanin and primary amino groups of QDs surface, and then the photoluminescent energy of QDs would be transferred to the complex, leading to the fluorescence quenching of QDs. As a result, the fluorescent intensity of the SiO 2 @QDs@ms-MIPs was significantly decreased within 8 min, and accordingly a favorable linearity within 0.02−0.8 μM and a high detectability of 5.9 nM were presented. Excellent recognition specificity for phycocyanin over its analogues was displayed, with a high imprinting factor of 4.72. Furthermore, the validated probe strategy was successfully applied to seawater and lake water sample analysis, and high recoveries in the range of 94.0−105.0% were attained at three spiking levels of phycocyanin, with precisions below 5.3%. The study provided promising perspectives to develop fluorescent probes for convenient, rapid recognition and sensitive detection of trace proteins from complex matrices, and further pushed forward protein imprinting research.

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Section: Introductionmentioning

confidence: 99%

Quantum Dots Based Mesoporous Structured Imprinting Microspheres for the Sensitive Fluorescent Detection of Phycocyanin

Zhong

Wang

et al. 2015

ACS Appl. Mater. Interfaces

138

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“…2,12 However, very few of these probes react with thiols rapidly enough to achieve real-time detection in vivo. And most of these probes can only respond to thiols statically.…”

mentioning

confidence: 99%

A fluorescent probe for rapid detection of thiols and imaging of thiols reducing repair and H₂O₂oxidative stress cycles in living cells

et al. 2013

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A diselenide containing fluorescent probe based on a fluorescein scaffold for thiols was developed. The fluorescent probe exhibited rapid response, high selectivity and reversibility. Confocal fluorescence microscopy was used to visualize the redox changes mediated by thiols and reactive oxygen species in living HeLa cells.Intracellular thiols play an essential role in maintaining redox homeostasis by regulating the redox status between reduced free thiols and oxidized disulfides.1 Glutathione (GSH), which has been identified as the most abundant non-protein thiol, is considered to be the main player in combating oxidative stress and regulating the redox environment of the internal cellular compartments. Further development of intracellular thiol detection methods is necessary to understand the complicated roles of thiols in redox biology and elucidate the pathogenesis of various disorders in living systems. Compared with other approaches, fluorescence imaging is less invasive, more sensitive and more convenient. 11Numerous fluorescent probes for thiols based on Michael addition, aldehyde cyclization, fluorophore deprotection, and thiol-disulfide exchange protocols have been reported. 2,12 However, very few of these probes react with thiols rapidly enough to achieve real-time detection in vivo. And most of these probes can only respond to thiols statically. Research has shown that fluorescent probes which are capable of responding to thiols and ROS reversibly offer better chances of visualizing redox signaling, stress, and thiols repair. Real-time methods for measuring thiols in vivo based on redoxsensitive green fluorescent protein have been reported. 1,14 However, such techniques require gene manipulation while redox-responsive probes based on small molecules are scarce. 13,15Glutathione peroxidase (GPx) is a selenoenzyme that protects various organisms from oxidative damage by catalyzing ROS reduction in the presence of GSH. 16 To clarify the catalytic mechanism of GPx and develop antioxidant drugs, researchers have synthesized many organoselenium compounds as GPx mimics, in which monoselenides, diselenides, and ebselen analogs are the major ones. 16,17 Steinmann et al. 18 recently reported that the cleavage of diselenide bonds by thiols is 5 orders of magnitude faster than that of disulfide bonds. Building on these results, we designed and synthesized a diselenide-based fluorescent probe (FSeSeF, Scheme 1) for the rapid detection of thiols and redox changes mediated by thiols and ROS in living cells. FSeSeF is a weakly fluorescent molecule that contains a diselenide bond as a fast, reversible recognition center for thiols and two fluoresceins as signal reporters. Once FSeSeF is cleaved by GSH, both the selenenyl sulfide FSeSG and the Scheme 1 Structure of FSeSeF and the nucleophilic attack by GSH at Se-Se bond with the generation of selenenyl sulfide FSeSG and selenol FSeH.

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“…The difunctional reagents are composed of PS, fluorophore (PL) and a disulfide bond (—S—S—), which can be cleaved by thiols such as Cys and GSH (Figure 17). 61 The iodine‐BODIPY acts as PS and FRET‐donor, while BODIPY serves as fluorescence unit and the FRET‐acceptor. In the absence of thiols, the generation of 1 O 2 can be quenched by FRET from iodine‐BODIPY to BODIPY and the fluorescence of BODIPY can be inhibited by the 2,4‐dinitrobenzenesulfonate moieties (DNBS).…”

Section: Fret Regulation Mechanismmentioning

confidence: 99%

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

et al. 2017

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With singlet oxygen (1O2) as the active agent, photodynamic therapy (PDT) is a promising technique for the treatment of various tumors and cancers. But it is hampered by the poor selectivity of most traditional photosensitizers (PS). In this review, we present a summary of controllable PDT implemented by regulating singlet oxygen efficiency. Herein, various controllable PDT strategies based on different initiating conditions (such as pH, light, H2O2 and so on) have been summarized and introduced. More importantly, the action mechanisms of controllable PDT strategies, such as photoinduced electron transfer (PET), fluorescence resonance energy transfer (FRET), intramolecular charge transfer (ICT) and some physical/chemical means (e.g. captivity and release), are described as a key point in the article. This review provide a general overview of designing novel PS or strategies for effective and controllable PDT.

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Fluorescent and colorimetric probes for detection of thiols

Cited by 1,506 publications

References 108 publications

Quantum Dots Based Mesoporous Structured Imprinting Microspheres for the Sensitive Fluorescent Detection of Phycocyanin

Quantum Dots Based Mesoporous Structured Imprinting Microspheres for the Sensitive Fluorescent Detection of Phycocyanin

A fluorescent probe for rapid detection of thiols and imaging of thiols reducing repair and H₂O₂oxidative stress cycles in living cells

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

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Fluorescent and colorimetric probes for detection of thiols

Cited by 1,506 publications

References 108 publications

Quantum Dots Based Mesoporous Structured Imprinting Microspheres for the Sensitive Fluorescent Detection of Phycocyanin

Quantum Dots Based Mesoporous Structured Imprinting Microspheres for the Sensitive Fluorescent Detection of Phycocyanin

A fluorescent probe for rapid detection of thiols and imaging of thiols reducing repair and H2O2oxidative stress cycles in living cells

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

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A fluorescent probe for rapid detection of thiols and imaging of thiols reducing repair and H₂O₂oxidative stress cycles in living cells