A highly sensitive fluorescent probe for detection of benzenethiols in environmental samples and living cells

Lin, Weiying; Long, Lingliang; Tan, Wen

doi:10.1039/b922478e

Cited by 173 publications

(102 citation statements)

References 30 publications

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“…[4] Indeed,t hese long-wavelength 7-hydroxycoumarins are popularp henol-based fluorophores currently used in the designo f" turn-on"r eactive probes( also known as fluorescent chemodosimeters) for in vitro detection and/or cell imagingo fv arious (bio)analytes. [9][10][11] Interestingly, pertinent studies concerning their solubilization in water and site-specific introduction of ab ioconjugatable handle within their core structure have recently been published. [12,13] Furthermore, the appended N-aryl moiety introduced through the transimination step could be exploited both to introduce further chemical diversity into the targeted fluorescent "Borico" scaffold and to increaset he stability of its BF 2 -chelate moiety.…”

Section: Introductionmentioning

confidence: 99%

New 3‐(Heteroaryl)‐2‐iminocoumarin‐based Borate Complexes: Synthesis, Photophysical Properties, and Rational Functionalization for Biosensing/Biolabeling Applications

Roubinet

Massif

Moreau

et al. 2015

Chemistry A European J

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Members of a series of boron difluoride complexes with 3-(heteroaryl)-2-iminocoumarin ligands bearing both a phenolic hydroxyl group (acting as a fluorogenic center) and an N-aryl substituent (acting as a stabilizing moiety) have been synthesized in good yields by applying a straightforward two-step method. These novel fluorogenic dyes belong to the family of "Boricos" (D. Frath et al., Chem. Commun.- 2013, 49, 4908-4910) and are the first examples of phenol-based fluorophores of which the photophysical properties in the green-yellow spectral range are dramatically improved by N,N-chelation of a boron atom. Modulation of their fluorescence properties through reversible chemical modification of their phenol moieties has been demonstrated by the preparation of the corresponding 2,4-dinitrophenyl (DNP) ethers, which led to a dramatic "OFF-ON" fluorescence response upon reaction with thiols. Additionally, to expand the scope of these "7-hydroxy-Borico" derivatives, particularly in biolabeling, amine or carboxylic acid functionalities amenable to (bio)conjugation have been introduced within their scaffold. Their utility has been demonstrated in the preparation of fluorescent bovine serum albumin (BSA) conjugates and "Borico"-DOTA-like scaffolds in an effort to design novel monomolecular multimodal fluorescence- radioisotope imaging agents.

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Section: Introductionmentioning

confidence: 99%

New 3‐(Heteroaryl)‐2‐iminocoumarin‐based Borate Complexes: Synthesis, Photophysical Properties, and Rational Functionalization for Biosensing/Biolabeling Applications

Roubinet

Massif

Moreau

et al. 2015

Chemistry A European J

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“…Phenyl hydrogen phthalate, 37 2-(trimethylsilyl)ethyl hydrogen phthalate, 40 and 3-(2-benzothiazolyl)-7-hydroxycoumarin 41 were prepared by published procedures. All NMR matched the known spectra.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Self-Immolative Aryl Phthalate Esters

2012

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We report that aryl phthalate esters are robust self-immolative linkers. This linker is easy to conjugate and releases output phenols upon cleaving a fluoride-sensitive mask to yield a benign phthalic acid byproduct, making these linkers potentially useful as fluoride sensors and promising for use in biological and materials applications. ABSTRACT: We report that aryl phthalate esters are robust selfimmolative linkers. This linker is easy to conjugate and releases output phenols upon cleaving a fluoride-sensitive mask to yield a benign phthalic acid byproduct, making these linkers potentially useful as fluoride sensors and promising for use in biological and materials applications. Disciplines

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“…Although it has been reported that 2,4-dinitrophenyl ether reacts with thiol, [17] we needed to examine whether its reactivity is appropriate for this design strategy under physiological conditions. Therefore, we preliminarily examined the fluorescence properties and reactivity of compounds 2-4 without the NTA-Ni 2 + moiety with glutathione (GSH) in HEPES buffer (100 mm, pH 7.4).…”

Section: Resultsmentioning

confidence: 99%

Selective Two‐Step Labeling of Proteins with an Off/On Fluorescent Probe

Hirabayashi

Hanaoka

Shimonishi

et al. 2011

Chemistry A European J

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We present a novel design strategy for off/on fluorescent probes suitable for selective two-step labeling of proteins. To validate this strategy, we designed and synthesized an off/on fluorescent probe, 1-Ni(2+), which targets a cysteine-modified hexahistidine (His) tag. The probe consists of dichlorofluorescein conjugated with nitrilotriacetic acid (NTA)-Ni(2+) as the His-tag recognition site and a 2,4-dinitrophenyl ether moiety, which quenches the probe's fluorescence by photoinduced electron transfer (PeT) from the excited fluorophore to the 2,4-dinitrophenyl ether (donor-excited PeT; d-PeT) and also has reactivity with cysteine. His-tag recognition by the NTA-Ni(2+) moiety is followed by removal of the 2,4-dinitrophenyl ether quencher by proximity-enhanced reaction with the cysteine residue of the modified tag; this results in a marked fluorescence increase. Addition of His-tag peptide bearing a cysteine residue to aqueous probe solution resulted in about 20-fold fluorescence increment within 10 min, which is the largest fluorescence enhancement so far obtained with a visible light-excitable fluorescent probe for a His-based peptide tag. Further, we successfully visualized CysHis(6)-peptide tethered to microbeads without any washing step. The probe also showed a large fluorescence increment in the presence of His(6)Cys-tagged enhanced blue fluorescent protein (EBFP), but not His(6)-tagged EBFP. We consider this system is superior to large fluorescence tags (e.g., green fluorescent protein: 27 kDa), which can perturb protein folding, trafficking and function, and also to existing small tags, which generally show little fluorescence increase upon target recognition and therefore require a washout step. This strategy should also be applicable to other tags.

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A highly sensitive fluorescent probe for detection of benzenethiols in environmental samples and living cells

Abstract: A highly sensitive fluorescent probe with a detection limit of 1.8 x 10(-9) M was constructed and employed to detect benzenethiols in environmental samples and living cells.

Cited by 173 publications

References 30 publications

New 3‐(Heteroaryl)‐2‐iminocoumarin‐based Borate Complexes: Synthesis, Photophysical Properties, and Rational Functionalization for Biosensing/Biolabeling Applications

New 3‐(Heteroaryl)‐2‐iminocoumarin‐based Borate Complexes: Synthesis, Photophysical Properties, and Rational Functionalization for Biosensing/Biolabeling Applications

Self-Immolative Aryl Phthalate Esters

Selective Two‐Step Labeling of Proteins with an Off/On Fluorescent Probe

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