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Fluorescent probe with near-infrared specificity for detecting cysteine

A technology of cysteine ​​and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of inability to distinguish cysteine ​​and homocysteine, etc., achieve strong tissue penetration, less damage to biological tissues, and eliminate Effect of tissue fluorescence background interference

Inactive Publication Date: 2019-02-12
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the fluorescent probe provided in the patent CN 104447421A cannot distinguish between cysteine ​​and homocysteine

Method used

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  • Fluorescent probe with near-infrared specificity for detecting cysteine
  • Fluorescent probe with near-infrared specificity for detecting cysteine
  • Fluorescent probe with near-infrared specificity for detecting cysteine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Compound I

[0025] (5) Under nitrogen protection and ice bath conditions, compound II was dissolved in anhydrous dichloromethane, then acryloyl chloride was added, and triethylamine was added dropwise into the reaction system. Stir overnight at room temperature. The crude product was obtained, which was purified by column chromatography to obtain red compound I. figure 1 is the NMR image of the probe.

Embodiment 2

[0026] Embodiment 2 Probe compound I selectivity analysis

[0027] Add 10 μM of compound I to the DMSO / PBS buffer containing cysteine ​​(the concentration of cysteine ​​is 200 μM, pH = 7.4, DMSO:PBS buffer with a volume ratio of 1:4), and the detection results are as follows: figure 2 , when the excitation light wavelength is 580nm, the probe compound I has a strong fluorescence response to cysteine ​​at 645 nm, and the probe compound I has no obvious response to other biological thiols, indicating that the probe compound I has a strong fluorescence response to cysteine Amino acids have excellent selectivity.

Embodiment 3

[0028] Example 3 Analysis of the response of probe compound I to changes in cysteine ​​concentration and a working curve for quantitative detection

[0029] Add 10 μM probe compound I to the buffer containing different concentrations of cysteine ​​(0 - 200 μM), the fluorescence response intensity increases regularly with the increase of the amount of cysteine ​​added, and the detection results are as follows: image 3 , the results show that the probe compound I has a wider detection range and higher sensitivity to cysteine ​​concentration. By plotting the concentration of cysteine ​​against the corresponding fluorescence value, a better linear working curve can be obtained, which can be used for the quantitative detection of cysteine.

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Abstract

The invention discloses a fluorescent probe for detecting cysteine, and belongs to the technical field of analytic chemistry. The probe is obtained by stirring 2-((6-hydroxy-2,3-dihydro-1H-xanthene-4-yl) methylene) malononitrile and acryloyl chloride in dichloromethane at the room temperature. The fluorescent probe has the advantages of being convenient to use, being high in selectivity and sensitiveness and low in detection limit on cysteine, and can be applied to detection of cysteine in cells.

Description

technical field [0001] The invention provides a fluorescent probe for detecting cysteine, belonging to the technical field of fluorescent probes. technical background [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy), and glutathione (GSH) are three very important small molecule biothiols in cells, which maintain various physiological balances of living organisms. Studies have shown that excessive Cys concentration is a major cause of cardiovascular disease and Alzheimer's disease, and Cys concentration in plasma has a great relationship with birth defects and Alzheimer's disease. Therefore, it is of great value in life science and medicine to realize the fluorescence imaging of cysteine ​​in cells and to give information on the expression and distribution of cysteine ​​in cells. [0003] At present, methods for measuring cysteine ​​content include gas chromatography-mass spectrometry, high performance liquid chromatography, fully automatic fluorescence polarization immunoass...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64
CPCC07D311/82C09K11/06C09K2211/1088G01N21/6428G01N21/643G01N21/6486
Inventor 吕正亮路亚男范春华
Owner UNIV OF JINAN
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