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Synthesis of multi-signal fluorescent probes and their application in the detection of cys, gsh and hcy

A fluorescent probe and fluorescent molecular probe technology, applied in the field of analytical chemistry, can solve the problems of sensitivity, low imaging signal-to-background ratio, poor selectivity, and low sensitivity

Active Publication Date: 2022-05-27
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 probes and their application in the detection of cys, gsh and hcy
  • Synthesis of multi-signal fluorescent probes and their application in the detection of cys, gsh and hcy
  • Synthesis of multi-signal fluorescent probes and their application in the 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)dipropionate dimethyl ester

[0024] a. 3.0 g (5.68 mmol) 3,3'-((4-chloro-3-formyl-2-oxo-2 H -pyran-7-yl)azadiyl)dipropionate dimethyl ester was added to 20 mL of dichloromethane, followed by 615.2 mg (6.82 mmol) of n-butanethiol and 690.3 mg (5.68 mmol) of triethylamine, room temperature The reaction was stirred 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. Synthesis of probe dimethyl 3,3'-((3-(2-(benzo[ d ]thiazol-2-yl)-2-cyanovinyl)-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)dipropionate dimethyl ester, 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 the reaction was stirred at room temperature for 12 hours;

[0028] . After the reaction is completed, 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. Application of the multi-signal fluorescent probe of the present invention to simultaneously distinguish Cys, GSH and Hcy

[0030]The spectroscopic property experiment of the fluorescent molecular probe for detecting Cys, GSH and Hcy according to the present invention: the probe is dissolved in dimethyl sulfoxide (DMSO) to prepare a probe solution with a concentration of 1 mM, and the concentration is 1 mM Cys, GSH and Hcy 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 buffer solution in 2 The final volume ratio of the organic phase and the aqueous phase was kept at 4:6 for all tests (the total volume of each test sample was 2 mL). The fluorescence emission spectra of Cys and GSH were measured at the excitation wavelength, respectively; the specific test method for detecting Hcy wa...

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Abstract

The invention discloses the synthesis of a multi-signal fluorescent probe and its use in quantifying serum total cysteine ​​(Cys) and homocysteine ​​(Hcy), and simultaneously distinguishing Cys and glutathione in fluorescent imaging cells / living bodies (GSH) and Hcy application method, the chemical structure of the molecular probe is as follows:. The fluorescent probe disclosed in the patent of the present invention has multiple reaction sites with controllable activity, which can realize the detection of Cys ( lambda ex / lambda em =360 / 453 nm), GSH ( lambda ex / lambda em =415 / 513 nm) and Hcy ( lambda ex / lambda em =488 / 542 nm). With good selectivity, high sensitivity, and strong anti-interference, it can be used to directly and simultaneously quantify the total Cys and Hcy levels in plasma, and at the same time distinguish Cys, GSH, and Hcy in fluorescent imaging cells / living bodies.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to the synthesis of a multi-signal fluorescent probe, and the preparation of the probe to directly quantify total Cys and Hcy in plasma, quantitatively detect Cys, GSH and Hcy simultaneously in the environment, and use the probe in biological samples. It is applied in devices that simultaneously differentiate fluorescent imaging Cys, GSH and Hcy. Background technique [0002] Homocysteine ​​is a sulfur-containing amino acid, which is a non-essential amino acid in the human body. It is the methionine in the human body that is metabolized in protein into 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 significant impact on human health. In recent years, studies have found that blood ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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