A fluorescent probe for the specific detection of cysteine in human serum samples

Huang, Zhen; Wu, Cuiyan; Li, Yaqian; Zhou, Zile; Xie, Rui-Hua; Pang, Xiao; Xu, Hai; Li, Haitao; Zhang, Youyu

doi:10.1039/c9ay00659a

Cited by 30 publications

(15 citation statements)

References 61 publications

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“…To further explore the versatility of DXM in the complex systems, it was applied to detect Cys in human serum samples by standard addition methods. Based on dilution experiments, the concentration of Cys in 30-fold diluted human serum samples was 6.00 μM, meaning the total concentration of Cys in human serum was 180.0 μM, which was in accordance with the results as reported in literature (the concentrations of Cys in human serum were 165.1-335.3 μM) [3,51]. Furthermore, different standard concentrations of Cys (0, 4, 9, and 14 μM) were added to 30-fold diluted serum samples in the recovery experiment, and satisfactory recovery rates were ranged from 98.56 to 100.50% (Table 1), indicating that DXM can be used as an excellent tool for the detection of Cys in complex systems.…”

Section: Determination Of Cys In Human Serumsupporting

confidence: 90%

“…Small-molecule fluorescent probe, as a useful tool, has been widely used in recent years due to the advantages of controllable structure, sensitive response, high selectivity, low toxicity, and excellent cell permeability [1][2][3][4][5][6]. However, the emission wavelength of conventional fluorescent probes is usually less than 550 nm, which limits their further applications in vivo.…”

Section: Introductionmentioning

confidence: 99%

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A near-infrared excitation/emission fluorescent probe for imaging of endogenous cysteine in living cells and zebrafish

Xie

Zhou

et al. 2020

Anal Bioanal Chem

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The fluorescence imaging technique provides an essential tool for studying biological systems. However, due to the interference of autofluorescence of biological tissues, the application of short-wavelength fluorescent probes in biological imaging was limited. The near-infrared (NIR) excitation/emission fluorescent probe possesses unique advantages in optical imaging in vivo, including less light scattering, minimal photo-damage to biological samples, deep tissue penetration, and weak autofluorescence interference from complicated biological systems. In this work, a convenient fluorophore (E)-2-[2-(6-hydroxy-2,3dihydro-1H-xanthen-4-yl)vinyl]-3-methylbenzo[d]thiazol-3-ium iodide (DXM-OH) with NIR excitation and emission was rationally designed and developed. What's more, DXM-OH was applied to construct an "OFF-ON" fluorescent probe (E)-2-{2-[6-(acryloyloxy)-2,3-dihydro-1H-xanthen-4-yl]vinyl}-3-methylbenzo[d]thiazol-3-ium iodide (DXM) for sensitive and selective detection of cysteine (Cys). The experimental results showed that DXM had the advantages of good cell permeability, low toxicity, and excellent optical properties (NIR excitation/emission) and it was successfully applied to image Cys of living cells and zebrafish.

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Section: Determination Of Cys In Human Serumsupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

A near-infrared excitation/emission fluorescent probe for imaging of endogenous cysteine in living cells and zebrafish

Xie

Zhou

et al. 2020

Anal Bioanal Chem

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“…Upon the gradual addition of Al ions, the emission band of DHT-K shifted from 541 to 495 nm with a gradual increase in intensity; no further change in intensity was observed when the Al ion concentration reached 247 µM (Figure 2a). In addition, to elucidate the sensitivity of DHT-K to Al ions, LOD was determined to be 1.84 µM using the slope of the calibration curve ranging in Al ion concentrations from 0 to 247 µM, in which the correlation coefficient (R 2 ) was determined to be 0.991 (Figure 2b) [31]. As the Al ion concentration in drinking water is strictly limited by the WHO to 7.41 µM, DHT-K was found suitable for measuring Al ion concentration in drinking water.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Single Benzene-Based Fluorophore for Selective Recognition of Al Ions

Lee

Cho

et al. 2022

Chemosensors

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Though 2,5-dihydroxyterephthalic acid (DHT) is composed of a single benzene molecule, it is blue-emissive in common organic solvents and in the solid state. Like most organic fluorophores, DHT is not soluble in water, which limits its versatile use in metal ion detection in an aqueous medium. To improve the water solubility of DHT and its use as a molecular sensor in aqueous solutions, its deprotonated form, DHT-K, was synthesized through the simple one-pot reaction of DHT with KOH. Compared with DHT, DHT-K was highly soluble in water and emitted yellow fluorescence in the solution and the solid. In addition, DHT-K showed high selectivity for Al ions, exhibiting fluorescence wavelength changes from 540 to 495 nm depending on the Al ion concentration. A linear relationship between the fluorescence intensity of DHT-K and Al ion concentration was established ranging from 18.96 to 247 μM with a detection limit of 1.84 µM. The binding stoichiometry between DHT-K and Al ions was determined by Job’s plot and found to be 1:2. Upon exposure to Al ions, DHT-K showed significant changes in fluorescence color and emission wavelength, whereas no fluorescence changes were observed by the addition of various metal ions such as Zn2+, Mg2+, Ca2+, Cu2+, Fe3+, and Co2+. Thus, DHT-K can be applied as a fluorescent sensor that can selectively detect Al ions in aqueous solutions.

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“…The detection of cysteine and glucose was also conducted in the human serum of a male AB plasma. The UV–vis spectra were measured, and the concentration of cysteine/glucose was calculated by employing the regression curve by the method described earlier . The results from the three individual experiments were averaged.…”

Section: Methodsmentioning

confidence: 99%

Two-in-One Dual-Channel Boronic Ester Block Copolymer for the Colorimetric Detection of Cysteine and Glucose at Neutral pH

Sharma

Haldar

Lee

2021

ACS Sustainable Chem. Eng.

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Developing a chemosensor to recognize more than one biologically important molecule from a single polymeric entity is essential. In this study, a block copolymer probe [PPBA-b-PDMA (P1)] of (2-phenylboronic esters-1,3-dioxane-5-ethyl) methyl acrylate (PBA) and N,N′-dimethylacrylamide (DMA) was synthesized by reversible addition−fragmentation chain transfer polymerization using a cysteine-detectable aldehydefunctionalized azobenzene chain transfer agent. P1 was selfassembled in water to form micelles at neutral pH. The colorimetric detection was not observed upon adding cysteine to the micellar solution since water-soluble cysteine could not reach the aldehyde group of the azo receptor hidden in the micelles' center. However, with the introduction of glucose, micelles became swollen since the PPBA block changed its behavior to hydrophilic by transforming a boronic ester to boronic acid. Thus, the azo receptor became exposed to cysteine, leading to the colorimetric detection of cysteine. Glucose detection was also demonstrated by titrating P1 solution with glucose at a fixed amount of cysteine. Therefore, a unique platform with a dual-detection capacity of cysteine and glucose is proposed.

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A fluorescent probe for the specific detection of cysteine in human serum samples

Abstract: A turn-on fluorescent probe for cysteine with high selectivity was designed and synthetized. The probe can be used for “naked-eye” detection of Cys with an obvious color change from yellow to colorless. The probe could be applied for Cys detection in real human serum.

Cited by 30 publications

References 61 publications

A near-infrared excitation/emission fluorescent probe for imaging of endogenous cysteine in living cells and zebrafish

A near-infrared excitation/emission fluorescent probe for imaging of endogenous cysteine in living cells and zebrafish

Synthesis of a Single Benzene-Based Fluorophore for Selective Recognition of Al Ions

Two-in-One Dual-Channel Boronic Ester Block Copolymer for the Colorimetric Detection of Cysteine and Glucose at Neutral pH

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