A FRET-based ratiometric fluorescent probe for highly selective detection of cysteine based on a coumarin–rhodol derivative

Bai, Yu; Wu, Mingxia; Ma, Qiujuan; Wang, Chunyan; Sun, Jingguo; Tian, Meiju; Li, Jiansheng

doi:10.1039/c9nj03375k

Cited by 26 publications

(22 citation statements)

References 49 publications

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“…FRET sensors that use l -(7-hydroxycoumarin-4-yl)ethylglycine, an unnatural fluorescent amino acid, for glutamine and methionine have also been reported [ 323 , 324 ]. Beyond genetically encoded sensors, two irreversible FRET-based synthetic probes selective for cysteine with applications in mammalian cells are also recently available (Table 2) [ 325 , 326 ].…”

Section: Fluorescence Imagingmentioning

confidence: 99%

The Role of Amino Acids in Neurotransmission and Fluorescent Tools for Their Detection

Dalangin

Kim

Campbell

2020

IJMS

105

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Neurotransmission between neurons, which can occur over the span of a few milliseconds, relies on the controlled release of small molecule neurotransmitters, many of which are amino acids. Fluorescence imaging provides the necessary speed to follow these events and has emerged as a powerful technique for investigating neurotransmission. In this review, we highlight some of the roles of the 20 canonical amino acids, GABA and β-alanine in neurotransmission. We also discuss available fluorescence-based probes for amino acids that have been shown to be compatible for live cell imaging, namely those based on synthetic dyes, nanostructures (quantum dots and nanotubes), and genetically encoded components. We aim to provide tool developers with information that may guide future engineering efforts and tool users with information regarding existing indicators to facilitate studies of amino acid dynamics.

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Section: Fluorescence Imagingmentioning

confidence: 99%

The Role of Amino Acids in Neurotransmission and Fluorescent Tools for Their Detection

Dalangin

Kim

Campbell

2020

IJMS

105

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“…The linear regression equation was F = 63.5503 + 223.0080 × 10 6 × C ( r = 0.9988), where F denotes the measured fluorescence intensity, C represents the concentration of HOCl, and r is the linear correlation coefficient. The detection limit was calculated by three times standard deviation of blank solution [ 48 , 49 ]. The detection limit was found to be 1.5 × 10 −7 mol·L −1 for the fluorescent probe.…”

Section: Resultsmentioning

confidence: 99%

A Highly Selective Fluorescent Probe for Hypochlorous Acid in Living Cells Based on a Naphthalene Derivative

Sun

et al. 2022

International Journal of Analytical Chemistry

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Hypochlorous acid (HOCl) was crucial for maintaining the homeostasis in cells and plays vital roles in many physiological and pathological processes. In this work, a highly selective fluorescent probe for hypochlorous acid in living cells was constructed and prepared based on a naphthalene derivative. A naphthalene derivative was utilized as the fluorescent group, and N,N-dimethylthiocarbamate was applied as the selective recognition site for HOCl. Before adding HOCl, the fluorescent probe exhibited weak fluorescence. Upon adding HOCl, the fluorescent probe displayed remarkable fluorescence enhancement. The fluorescence intensity at 502 nm showed a linear response to the concentration of HOCl from 3.0 × 10−7 to 1.0 × 10−5 mol·L−1. The detection limit was estimated to be 1.5 × 10−7 mol·L−1 for HOCl. The fluorescent probe showed fast response and outstanding selectivity toward HOCl. It owned good biocompatibility and had also been successfully applied in the confocal imaging of exogenous and endogenous HOCl in living cells.

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“…0.4 g of 2 (1.8 mmol) and 0.3 g of 4 (1 mmol) were added to a 100 mL roundbottomed flask containing 20 mL of absolute ethanol and 0.5 mL of piperidine; the reaction mixture was stirred at 80 °C for 4 h under N 2 protection, and then, the mixture was subjected to rotary evaporation and purified by column chromatography (DCM/MeOH/HAc = 100:1:1, v/v/v) to afford KQ−SO 2 as a purple solid with a yield of 80%. 1 H NMR (400 MHz, DMSO-d 6 ): 9.14 (s, 1H), 8.68−8.64 (d, J = 16.0 Hz, 1H), 8.41−8.39 (d, J = 8.0 Hz, 1H), 8.28−8.26 (d, J = 8.0 Hz, 1H), 7.89−7.85 (dd, J 1 = 8.0 Hz, J 2 = 4.0 Hz, 3H), 7.74−7.61 (t, J = 26.0 Hz, 2H), 7.61−7.57 (m, 3H), 7.40−7.36 (t, J = 8.0 Hz, 1H), 4.59−4.54 (dd, J 1 = 8.0 Hz, J 2 = 4.0 Hz, 2H), 4.17 (s, 3H), 1.65 (s, 6H), 1.40−1.36 (t, J = 8.0 Hz, 3H); 13 Spectrophotometric Measurements. Fluorescence measurement experiments were measured in 10 mM phosphate buffer solution with DMSO as cosolvent solution (H 2 O/DMSO = 99:1, v/v).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…In recent years, the fluorescence detection imaging technology has shown many advantages, such as real-time detection, simple operation, less damage to the object under test, high sensitivity, and high selectivity, and has attracted more and more attention from scientific researchers. − Until now, many fluorescent sensors for detecting SO 2 were developed, which is based on nucleophilic addition reactions with the electron-deficit “CC”, ketone, or aldehyde groups and inhibition of CN isomerization. However, there are also many challenges for rapid and highly selective detection in real samples and biological systems.…”

Section: Introductionmentioning

confidence: 99%

Rational Development of a New Reaction-Based Ratiometric Fluorescent Probe with a Large Stokes Shift for Selective Detection of Bisulfite in Tap Water, Real Food Samples, Onion Tissues, and Zebrafish

Yuan

Zhou

Yang

et al. 2021

J. Agric. Food Chem.

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Bisulfite (HSO3 –) is usually widely added to tap water and food because it has antibacterial, bleaching, and antioxidant effects. However, its abnormal addition would cause a series of serious diseases related to it. Therefore, development of an effective method for HSO3 – detection was of great significance to human health. In this work, a new reaction-based ratiometric fluorescent probe KQ–SO2 was rationally designed, which could be used for the highly selective detection of HSO3– in tap water, real food samples, onion tissues, and zebrafish. Specifically, a positively charged benzo[e]indolium moiety and a carbazole group through a condensation reaction resulted in KQ–SO2, which displayed two well-resolved emission bands separated by 225 nm, fast response (1 min), and high selectivity and sensitivity toward HSO3– upon undergoing the Michael addition reaction, as well as low cytotoxicity in vitro. In addition, KQ–SO2 has been successfully applied for the detection of HSO3 – in tap water, real food samples, onion tissues, and zebrafish with satisfactory results. We predict that KQ–SO2 could be used as a powerful tool to reveal the relationship between HSO3– and the human health.

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A FRET-based ratiometric fluorescent probe for highly selective detection of cysteine based on a coumarin–rhodol derivative

Abstract: A ratiometric fluorescent probe for detecting cysteine was designed and synthesized based on the fluorescence resonance energy transfer (FRET) process.

Cited by 26 publications

References 49 publications

The Role of Amino Acids in Neurotransmission and Fluorescent Tools for Their Detection

The Role of Amino Acids in Neurotransmission and Fluorescent Tools for Their Detection

A Highly Selective Fluorescent Probe for Hypochlorous Acid in Living Cells Based on a Naphthalene Derivative

Rational Development of a New Reaction-Based Ratiometric Fluorescent Probe with a Large Stokes Shift for Selective Detection of Bisulfite in Tap Water, Real Food Samples, Onion Tissues, and Zebrafish

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