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Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in detection of Cys, GSH and Hcy

A technology of fluorescent probes and fluorescent molecular probes, applied in the field of analytical chemistry, can solve problems such as low sensitivity, poor selectivity, and unsatisfactory

Active Publication Date: 2021-07-30
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported fluorescent probes can only detect the added Hcy in plasma, and have problems such as low sensitivity and poor selectivity, and have not achieved direct and accurate quantification of Hcy and Cys in plasma / serum
At the same time, several small-molecule fluorescent probes have been reported to simultaneously distinguish Cys, GSH, and Hcy, but the sensitivity and imaging signal-to-background ratio are still low, and they cannot meet the needs of simultaneous imaging of endogenous thiols in cells / living bodies.

Method used

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  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in detection of Cys, GSH and Hcy
  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in detection of Cys, GSH and Hcy
  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in detection of Cys, GSH and Hcy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1. Synthesis of 3,3'-((4-(butylthio)-3-formyl-2-oxo-2 H -pyran-7-yl)azadiyl)dimethyl dipropionate

[0024] a. Add 3.0 g (5.68 mmol) 3,3'-((4-chloro-3-formyl-2-oxo-2 H -pyran-7-yl)azadiyl)dimethyl dipropionate was added to 20 mL of dichloromethane, and then 615.2 mg (6.82 mmol) of n-butanethiol and 690.3 mg (5.68 mmol) of triethylamine were added at room temperature Stirring and reacting for 6 hours;

[0025] b. After the reaction was completed, the solvent was spin-dried on a rotary evaporator, and purified by column chromatography to obtain 2.0 g of a yellow solid product with a yield of 78.3%.

Embodiment 2

[0026] Example 2. Synthetic probe dimethyl 3,3'-((3-(2-(benzo[ d ]thiazol-2-yl)-2-cyanoethenyl)-4-(butylthio)-2-oxo-2 H -pyran-7-yl)azadiyl)( E )-dipropionate

[0027] . 1.0 g (2.22 mmol) of 3,3'-((4-(butylthio)-3-formyl-2-oxo-2 H -pyran-7-yl)azadiyl)dimethyl dipropionate, 391.2 mg (2.25 mmol) 2-(benzo[ d ]thiazol-2-yl) acetonitrile and 38.3 mg (0.22 mmol) p-toluenesulfonic acid were added to 20 mL of absolute ethanol, and stirred at room temperature for 12 hours;

[0028] . After the reaction is complete, filter and recrystallize the filter cake with absolute ethanol to obtain the multi-signal fluorescent probe of the present invention.

Embodiment 3

[0029] Example 3. The application of the multi-signal fluorescent probe of the present invention to simultaneously distinguish Cys, GSH and Hcy

[0030]The spectroscopic property experiment of detecting Cys, GSH and Hcy with fluorescent molecular probes according to the present invention: the probes were dissolved in dimethyl sulfoxide (DMSO) to prepare a probe solution with a concentration of 1 mM, and the concentration of each preparation was 1 mM. Cys, GSH and Hcy in mM in water. The specific test method for detecting Cys / GSH is as follows: Take 20 μL of probe solution (1 mM), 780 μL of analytically pure DMSO, the required amount of 1 mM Cys / GSH aqueous solution and the required amount of PBS buffered aqueous solution in 2 In the sample tube of mL, the final volume ratio of the organic phase and the aqueous phase was maintained at 4:6 (the total volume of each test sample was 2 mL) for all tests. After shaking for 30 minutes at room temperature, the 360 ​​and 415 nm The ex...

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Abstract

The invention discloses synthesis of a multi-signal fluorescent probe and an application method of the multi-signal fluorescent probe in quantifying serum total cysteine (Cys) and homocysteine (Hcy) and simultaneously distinguishing Cys, glutathione (GSH) and Hcy in fluorescence imaging cells / living bodies. The chemical structural formula of the molecular probe is shown in the specification. The fluorescent probe disclosed by the invention has a plurality of reaction sites with controllable activity, and can be used for respectively detecting Cys (lambdaex / lambdaem = 360 / 453 nm), GSH (lambdaex / lambdaem = 415 / 513 nm) and Hcy (lambdaex / lambdaem = 488 / 542 nm) through three channels of blue, green and yellow. The fluorescent probe has the advantages of good selectivity, high sensitivity and strong anti-interference performance, and can be used for directly and simultaneously quantifying the total Cys and Hcy levels in plasma and simultaneously distinguishing Cys, GSH and Hcy in fluorescence imaging cells / living bodies.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and specifically relates to the synthesis of a multi-signal fluorescent probe, and the preparation of the probe to directly quantify the total Cys and Hcy in plasma, and the simultaneous quantitative detection of Cys, GSH and Hcy in the environment. Applications in devices that simultaneously differentiate Cys, GSH, and Hcy for fluorescence imaging. Background technique [0002] Homocysteine ​​is an amino acid containing sulfur molecules, which is a non-essential amino acid for the human body. It is metabolized in the body from methionine in the protein ingested by the human body to glutathione (the most important antioxidant in the body) and S-adenosylmethionine. (SAMe) intermediate. Under normal circumstances, Hcy in plasma is at a low level, but when Hcy in blood increases (≥ 10 μmol / L), it will have a major impact on human health. In recent years, studies have found that the lev...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/643G01N21/6428G01N21/6456G01N21/6486C09K2211/1037C09K2211/1088
Inventor 尹鹏尹国兴甘亚兵喻婷李海涛
Owner HUNAN NORMAL UNIVERSITY
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