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Fluorine-boron skeleton-based fluorescent probe TQBF-NBD with large Stokes displacement, and preparation method and application of fluorescent probe TQBF-NBD

A technology of TQBF-NBD and TQBF-OH, applied in the field of fluorescent probes, can solve the problems of low detection sensitivity and separate detection of biothiols

Pending Publication Date: 2020-12-22
河南凯普瑞生物技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The present invention proposes a fluorescent probe TQBF-NBD with a large Stokes shift based on a fluorine-boron skeleton and its preparation method and application, which solves the problem of the low detection sensitivity of existing biothiols and the inability to quickly and clearly distinguish Cys / Hcy from GSH open technical issues

Method used

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  • Fluorine-boron skeleton-based fluorescent probe TQBF-NBD with large Stokes displacement, and preparation method and application of fluorescent probe TQBF-NBD
  • Fluorine-boron skeleton-based fluorescent probe TQBF-NBD with large Stokes displacement, and preparation method and application of fluorescent probe TQBF-NBD
  • Fluorine-boron skeleton-based fluorescent probe TQBF-NBD with large Stokes displacement, and preparation method and application of fluorescent probe TQBF-NBD

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Effect test

Embodiment 1

[0037] The preparation method of the fluorescent probe TQBF-NBD based on the large Stokes shift of the fluorine boron skeleton, the technical route is as follows:

[0038]

[0039] The preparation steps are as follows:

[0040] (a) Dissolve 2,4-diethyl-1,2,3,4-tetrahydroquinoxaline salicylaldehyde (234 mg, 1.0 mmol), p-aminophenol (121 mg, 1.2 mmol) and a catalytic amount of TsOH In 5 mL of ethanol, heated to reflux under the protection of argon for 2 hours, stopped the reaction, cooled the reaction solution to room temperature, and spin-dried to obtain a dark brown oily liquid crude product;

[0041] (b) Dissolve 200 μL of crude product in 10 mL 1,2-dichloroethane, then add 100 μL DIEA and 100 μL BF 3 •OEt 2 , reacted at 80 °C for 4 h under the protection of argon, stopped the reaction, added 30 mL of 1,2-dichloroethane to the reaction liquid, poured it into 100 mL of NaHCO 3 In the solution, the organic phase was separated, the aqueous phase was extracted 3 times with ...

Embodiment 2

[0045] The preparation method of the fluorescent probe TQBF-NBD based on the large Stokes shift of the fluorine boron skeleton, the technical route is as follows:

[0046]

[0047] The preparation steps are as follows:

[0048] (a) Dissolve 2,4-diethyl-1,2,3,4-tetrahydroquinoxaline salicylaldehyde (234 mg, 1.0 mmol), 1 mmol of p-aminophenol and 0.05 mmol of TsOH in 5 mL of ethanol , heated to reflux for 2 hours under argon protection, stopped the reaction, cooled the reaction solution to room temperature, and spin-dried to obtain a dark brown oily liquid crude product;

[0049] (b) Dissolve 250 μL of crude product in 10 mL 1,2-dichloroethane, then add 100 μL DIEA and 100 μL BF 3 •OEt 2 , reacted at 80 °C for 4 h under the protection of argon, stopped the reaction, added 30 mL of 1,2-dichloroethane to the reaction liquid, poured it into 100 mL of NaHCO 3 In the solution, the organic phase was separated, the aqueous phase was extracted 3 times with dichloromethane (3 × 30 ...

Embodiment 3

[0052] The preparation method of the fluorescent probe TQBF-NBD based on the large Stokes shift of the fluorine boron skeleton, the technical route is as follows:

[0053]

[0054] The preparation steps are as follows:

[0055] The preparation steps are as follows:

[0056] (a) Dissolve 2,4-diethyl-1,2,3,4-tetrahydroquinoxaline salicylaldehyde (234 mg, 1.0 mmol), 1.1 mmol of p-aminophenol and 0.05 mmol of TsOH in 5 mL In ethanol, heated to reflux for 2 hours under the protection of argon, the reaction was stopped, the reaction solution was cooled to room temperature, and spin-dried to obtain a dark brown oily liquid crude product;

[0057] (b) Dissolve 230 μL of the crude product in 10 mL of 1,2-dichloroethane, then add 100 μL of DIEA and 100 μL of BF 3 •OEt 2 , reacted at 80 °C for 4 h under the protection of argon, stopped the reaction, added 30 mL of 1,2-dichloroethane to the reaction liquid, poured it into 100 mL of NaHCO 3 In the solution, the organic phase was sep...

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Abstract

The invention belongs to the field of fluorescent probes, and relates to a fluorescent probe based on a fluorine-boron skeleton, in particular to a fluorine-boron skeleton-based fluorescent probe TQBF-NBD with large Stokes displacement, and a preparation method and application of the fluorescent probe TQBF-NBD. The fluorescent probe TQBF-NBD has a structural formula as shown in the specification.The molecule of the probe does not have fluorescence, and emits red and green fluorescence after reacting with biological mercaptan. The probe molecule provided by the invention not only can qualitatively analyze the biological mercaptan, but also can realize rapid and quantitative detection of the biological mercaptan, and has important application value in the fields of biochemistry and the like.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, and relates to a fluorescent probe based on a boron-fluorine skeleton, in particular to a fluorescent probe TQBF-NBD with a large Stokes shift based on a boron-fluorine skeleton and a preparation method and application thereof. Background technique [0002] Biothiol is a general term for thiol-containing compounds in organisms, which widely exist in organisms. The most representative biothiols are three sulfhydryl compounds: cysteine ​​(Cys), homocysteine ​​(Hcy) and Glutathione (GSH). Sulfhydryl compounds are important signaling molecules after the function of biological enzymes and physiological activities. At the same time, thiol compounds can also regulate the normal redox state of cells and have important functions in the physiological activities of living organisms. The abnormal concentration of thiol compounds in organisms is related to many diseases. The lack of Cys is related to diseas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/6428C09K2211/1048C09K2211/1062C09K2211/107G01N2021/6432
Inventor 王辉宋相志任晓杰李小佳
Owner 河南凯普瑞生物技术有限公司
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