Ratiometric Fluorescent Probes for the Detection of Reactive Oxygen Species

Andina, Diana; Leroux, Jean‐Christophe; Luciani, Paola

doi:10.1002/chem.201702458

Cited by 113 publications

(63 citation statements)

References 170 publications

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“…Ar epresentative chemodosimeter is composed of af luorophore moiety as the signaling unit linked with af unctional group, which acts as as pecific responses ite for the analytes.T he observable optical signal from an analyte-specific bioorthogonal reactioni sm ostly irreversible among reaction-based fluorescent probes. [10][11][12][13][14][15][16][17] To successfully develop ar eaction-based fluorescent probe, the choice of signaling unit is crucial to obtain favorable optical properties for the probe. Among the various scaffolds of fluorophores, 4,4-difluoro-4-borata-3a,4a-diaza-s-indacene (BODIPY)d yes ( Figure 1) have been recognized as promising candidates for the construction of fluorescent probeso wing to their outstanding characteristics, such as high molar absorption coefficient, favorable fluorescenceq uantum yield, excellent chemicala nd photo stability, low sensitivityt ot he polarity of solvents, as well as insensitivityt op H. [18] Severale xcellent reviewsh ighlighting BODIPY-based fluorescent probesf or metal ions, reactive oxygen species( ROS), reactive nitrogen species(RNS), and pH have been reported.…”

Section: Introductionmentioning

confidence: 99%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

190

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Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

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Section: Introductionmentioning

confidence: 99%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

190

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“…Compared with other Cu 2+ probes (Table ), the detection limit of this method was lower . This good performance might be attributed to the special nanostructures of CDs/BSA–AuNCs, which produced slight fluorescence resonance energy transfer from CD to BSA–AuNCs, and the ratiometric detection method …”

Section: Resultsmentioning

confidence: 99%

Ratiometric fluorescence detection of Cu²⁺ based on carbon dots/bovine serum albumin–Au nanoclusters

Yang

Zeng

et al. 2018

Luminescence

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A ratiometric fluorescence sensor for Cu 2+ detection was developed by employing carbon dots (CDs) as the reference fluorophore, and bovine serum albumin (BSA)-Au nanoclusters (AuNCs) both as specific recognition element and as response signal.The CDs were prepared by heating an acetic acid solution of chitosan at 180°C. The proposed nanoprobe was prepared by simply mixing the CDs and BSA-AuNCs. Here, the CDs were associated with BSA-AuNCs to form CDs/BSA-AuNCs nanoprobes based on electrostatic interaction and hydrogen bonds. In the hybrid fluorescent CDs/BSA-AuNCs nanoprobe, the emission of BSA-AuNCs at 640 nm was quenched by Cu 2+ , whereas the emission of CDs at 424 nm was maintained. The fluorescence changes of I 640 /I 424 had good linearity with Cu 2+ concentration in the range 1.5-600 nM, and the detection limit of the nanoprobe was 0.5 nM for Cu 2+ detection, almost 4 × 10 4 times lower than the maximum allowable amount of Cu 2+ in drinking water. The proposed method for detecting Cu 2+ also had high selectivity and feasibility.

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“…Another method, Magnetic Resonance Imaging (MRI) [13,14], is often too expensive and time consuming to be broadly used for monitoring the oxidative stress on the cellular level (in vitro and in vivo). ROS can also be monitored by fluorescence imaging [12,15,16], a technique employing molecules of a fluorescence probe (FP) that allows for the observation of processes in single cells or their parts (via confocal microscopy) [17]. FP should react with ROS faster than other biomolecules and such a reaction should result in a clear fluorescence response (on/off), even at low concentrations of ROS.…”

Section: Initiationmentioning

confidence: 99%

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

et al. 2020

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Herein, we describe the synthesis of a fluorescent probe NB-2 and its use for the detection of peroxyl radicals. This probe is composed of two receptor segments (4-hydroxycinnamyl moieties) sensitive towards peroxyl radicals that are conjugated with a fluorescent reporter, dipyrrometheneboron difluoride (BODIPY), whose emission changes depend on the oxidation state of the receptors. The measurement of the rate of peroxidation of methyl linoleate in a micellar system in the presence of 1.0 µM NB-2 confirmed its ability to trap lipid peroxyl radicals with the rate constant kinh = 1000 M−1·s−1, which is ten-fold smaller than for pentamethylchromanol (an analog of α-tocopherol). The reaction of NB-2 with peroxyl radicals was further studied via fluorescence measurements in methanol, with α,α′-azobisisobutyronitrile (AIBN) used as a source of radicals generated by photolysis or thermolysis, and in the micellar system at pH 7.4, with 2,2′-azobis(2-amidinopropane) (ABAP) used as a thermal source of the radicals. The reaction of NB-2 receptors with peroxyl radicals manifests itself by the strong increase of a fluorescence with a maximum at 612–616 nm, with a 14-fold enhancement of emission in methanol and a 4-fold enhancement in the micelles, as compared to the unoxidized probe. Our preliminary results indicate that NB-2 behaves as a “switch on” fluorescent probe that is suitable for sensing peroxyl radicals in an organic lipid environment and in bi-phasic dispersed lipid systems.

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Ratiometric Fluorescent Probes for the Detection of Reactive Oxygen Species

Cited by 113 publications

References 170 publications

BODIPY‐Based Fluorescent Probes for Biothiols

BODIPY‐Based Fluorescent Probes for Biothiols

Ratiometric fluorescence detection of Cu²⁺ based on carbon dots/bovine serum albumin–Au nanoclusters

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

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Ratiometric Fluorescent Probes for the Detection of Reactive Oxygen Species

Cited by 113 publications

References 170 publications

BODIPY‐Based Fluorescent Probes for Biothiols

BODIPY‐Based Fluorescent Probes for Biothiols

Ratiometric fluorescence detection of Cu2+ based on carbon dots/bovine serum albumin–Au nanoclusters

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

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Ratiometric fluorescence detection of Cu²⁺ based on carbon dots/bovine serum albumin–Au nanoclusters