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A kind of pyrenylbenzimidazole fluorescent probe and its preparation method and application

A technology of pyrenylbenzimidazoles and dimethylbenzimidazoles, which is applied in the field of pyrenylbenzimidazoles fluorescent probes and their preparation, can solve the problem of low sensitivity, inability to realize heparin colorimetric/fluorescence dual-mode detection, Difficulty in synthesizing fluorescent probes and other issues to achieve the effects of improved sensitivity, easy separation and purification, and easy access to raw materials

Active Publication Date: 2022-05-17
HEBEI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of pyrenylbenzimidazole fluorescent probe and its preparation method and application, to solve the difficulty in synthesizing the fluorescent probe in the prior art, the sensitivity is low, and the colorimetric / fluorescence dual-mode detection of heparin cannot be realized And other issues

Method used

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  • A kind of pyrenylbenzimidazole fluorescent probe and its preparation method and application
  • A kind of pyrenylbenzimidazole fluorescent probe and its preparation method and application
  • A kind of pyrenylbenzimidazole fluorescent probe and its preparation method and application

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Embodiment 1

[0047] The synthesis of embodiment 1 PYNN

[0048] (1) Synthesis of Compound A

[0049]

[0050] Add 1,2-dimethylbenzimidazole 0.44g (3mmol) and (3-bromopropyl) dimethyl ammonium bromide 0.78g (3mmol) to a 50mL round bottom flask, acetonitrile 25mL, start stirring, and heat To 90 ° C, reflux reaction for 8h. Then, the reaction solution was cooled to room temperature, and the reaction solution was concentrated under reduced pressure to 1 / 2 of the original volume, and a white solid was precipitated, which was filtered under reduced pressure to obtain Compound A, which was subjected to the next step of reaction.

[0051] (2) Synthesis of compound PYNN

[0052]

[0053] Add 0.23g (1mmol) of 1-pyrene carboxaldehyde, 0.41g (1mmol) of compound A, 0.17g (2mmol) of piperazine, and 80mL of ethanol to a 150mL round bottom flask, start stirring, heat to 90°C, and stop the reaction after reflux for 24h reaction. Then, the reaction solution was cooled to room temperature, and the ...

Embodiment 2

[0056] The AIE property of embodiment 2 PYNN

[0057] Take 40 μL of the DMSO stock solution (concentration of 500 μM) of PYNN prepared in Example 1 and add it to a 2mL EP tube, then add different volume fractions of toluene and tetrahydrofuran (V 甲苯 :V 四氢呋喃 =0:10, 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2, 9:1, 10:0). The total volume of the solution was 1 mL, and the final concentration of PYNN was 20 μM. After the above solution was left at room temperature for 30 min, its fluorescence spectrum was measured (excitation wavelength: 325 nm).

[0058] image 3 is the fluorescence spectrum of PYNN in toluene-tetrahydrofuran mixed solution with a volume fraction of toluene of 0-100%. Such as image 3 As shown, as the volume fraction of toluene increases from 0 to 100%, the solubility of PYNN in the mixed solvent gradually decreases, and the fluorescence intensity gradually increases, indicating that its PYNN has typical AIE properties.

Embodiment 3

[0059] Example 3 Colorimetric / fluorescent dual mode response of PYNN to heparin

[0060] Add 40 μL of the DMSO stock solution of PYNN prepared in Example 1 (concentration: 500 μM) into a 2 mL EP tube, then add deionized water, HEPES solution (pH=7, concentration: 100 mM) 100 μL and different volumes of Heparin stock solution (50 μg / mL concentration), the total solution volume is 1 mL, the final concentration of PYNN is 20 μM, and the heparin concentration is 0-8 μg / mL. After the above solution was left at room temperature for 30 min, the absorption spectrum and fluorescence spectrum (excitation wavelength 325 nm) were measured.

[0061] Figure 4 is the absorption spectrum of PYNN after adding different concentrations of heparin; Figure 5 is the fluorescence spectrum of PYNN after adding different concentrations of heparin. Such as Figure 4 and Figure 5 As shown, with the increase of the concentration of heparin (0-8μg / mL), the absorbance of PYNN at 280nm and 370nm dec...

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Abstract

The present invention provides a pyrenylbenzimidazole fluorescent probe and its preparation method and application. The fluorescent probe has the structure shown in formula (I), and its preparation process is as follows: (1) 1, 2-di Tolylbenzimidazole and (3-bromopropyl) dimethyl ammonium bromide are added to acetonitrile, and heated to reflux, after the reaction is completed, compound A is isolated; (2) compound A and 1-pyrene formaldehyde are Heating to reflux in ethanol, after separation and purification, the fluorescent probe with the structure shown in formula (I) was obtained. The fluorescent probe of the invention can be used for the detection of heparin, and has the characteristics of simple synthesis, good water solubility, long luminescent wavelength, high sensitivity to heparin, strong selectivity, dual-mode response and wide application range.

Description

technical field [0001] The invention belongs to the technical field of medical detection, and in particular relates to a pyrenylbenzimidazole fluorescent probe and a preparation method and application thereof. Background technique [0002] Heparin is a highly sulfated linear glycosaminoglycan, mainly composed of iduronic acid, glucuronic acid and glucosamine, containing a large number of sulfonate and carboxylate groups, and is the highest known negative charge density Biomacromolecule. It is ubiquitous in organs such as the lung, heart, liver, pancreas and blood, and plays a vital role in controlling the body's immune defense mechanisms, cell growth and differentiation, lipid transport and metabolism, and preventing blood clot formation . Heparin can enhance the inhibitory effect of antithrombin on thrombin and other coagulation factors, relieve and inhibit the formation of thrombus, and is currently the most widely used anticoagulant drug in clinical practice. However, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/08C09K11/06G01N21/64G01N21/78
CPCC07D235/08C09K11/06G01N21/6428G01N21/78C09K2211/1011C09K2211/1044
Inventor 聂海亮梁晓萌闫宏远白洁张国伟杨晓溪
Owner HEBEI UNIVERSITY
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