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Fluorescent probe for detecting cysteine in cell

A technology of fluorescent probe and cysteine, which is applied in the field of analytical chemistry, can solve the problems of decreased hematopoietic function and slow growth, and achieves the effects of low preparation cost, high specificity and easy promotion

Inactive Publication Date: 2017-05-10
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when the concentration of cysteine ​​in the living body is abnormal, it often leads to decreased hematopoietic function, slow growth, etc.

Method used

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  • Fluorescent probe for detecting cysteine in cell
  • Fluorescent probe for detecting cysteine in cell
  • Fluorescent probe for detecting cysteine in cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of fluorescent probe for detecting cysteine ​​in cancer cells according to the present invention

[0028] Compound (1 mmol), (1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (2 mmol), 1-hydroxybenzotriazepam shown in formula (II) Add azole (1.5 mmol), triethylamine (2.2 mmol) and N,N-dimethylformamide (5 mL) into a 50 mL one-necked flask, stir at room temperature for 16 hours, cool to room temperature, add to water, filter, drying. The resulting solid was purified by column chromatography (dichloromethane:methanol=15:1) to obtain a dark red product, which is a fluorescent probe for detecting intracellular cysteine ​​according to the present invention, with a yield of 43%.

[0029] The above-mentioned fluorescent probes for detecting intracellular cysteine 1 H NMR spectrum see figure 1 .

Embodiment 2

[0031] The fluorescence spectrum of fluorescent probe of the present invention under different cysteine ​​concentrations

[0032] Cysteine ​​is supplied in aqueous solution using cysteine. Prepare ten 5 mL portions of 5 μM probe buffer solution containing 5% methanol in advance, and add cysteine ​​at a concentration of 0 to 150 μM. Fluorescence detection is then performed (λ Ex = 580 nm); Calculate the fluorescence intensity in each system; By analyzing the relationship between the fluorescence intensity at 630 nm and the concentration of cysteine, evaluate the response performance of the probe to cysteine ​​(see figure 2 and image 3 ). figure 2 It shows that with the increase of cysteine ​​concentration, the fluorescence intensity of the solution increases gradually. image 3 It is shown that when the concentration of sodium sulfide is in the range of 40-200 μM, the fluorescence intensity of the solution and the concentration of cysteine ​​are in a good linear relation...

Embodiment 3

[0034] Fluorescence spectra of fluorescent probes reacted with different substances

[0035] Prepare 10 parts of 5 mL of 5 μM probe buffer solution (containing 5% methanol, pH = 7.4), and then add 50 μL of 200 μM Hcys, Na 2 S, Na 2 SO 3 , NO, H 2 o 2 , HClO 4 , Cys, GSH, NaNO 2 , VC and other small molecules in PBS solution. Fluorescence detection is then performed (λ Ex = 580 nm); calculate the fluorescence intensity in each system; evaluate the interference of different substances to the fluorescent probe solution (see Figure 4 ). It can be seen from the figure that, of course, adding Hcys and Na to the probe solution 2 S, Na 2 SO 3 , NO, H 2 o 2 , HClO 4 , GSH, NaNO 2 , VC and other small molecules, only cysteine ​​can cause the solution to produce significant fluorescence, but the fluorescence of the solution basically does not change when other small molecules are added, which means that the probe only responds to cysteine, and basically does not Interfer...

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Abstract

The invention discloses a fluorescent probe for detecting cysteine in a cell. The fluorescent probe is a rhodamine dye derivative, and has a chemical structural formula shown in formula (I). The fluorescent probe is easy to prepare, low-cost and high in specificity, can be used for rapidly detecting the cysteine in the cell almost without interference of other components in a detection process, and has broad application prospect. (The chemical structural formula (I) is shown in the description.).

Description

technical field [0001] The invention relates to a novel fluorescent probe for detecting intracellular cysteine, which belongs to the technical field of analytical chemistry. Background technique [0002] Cysteine ​​(Cys) is a common amino acid in organisms, and it is the only amino acid with a reducing group thiol among more than 20 amino acids that make up proteins. In addition to being mainly distributed in the liver, spleen, and kidney, cysteine ​​also accumulates in large quantities on the surface of the human body, including skin and mucous membranes. In the living body, it has the physiological function of strengthening the defense ability of the living body itself and adjusting the defense mechanism of the living body. For example, it has coagulation effect. Experiments have proved that cysteine ​​has a certain detoxification effect on toxic substances such as formaldehyde, chloroform, lead, cadmium, methylmercury, and pufferfish poison, and can effectively prevent an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78C09K11/06G01N21/64
CPCC07D311/78C09K11/06C09K2211/1007C09K2211/1088G01N21/6428G01N21/6486
Inventor 林伟英董宝利王超孔秀琪宋学真张楠
Owner UNIV OF JINAN
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