Pyrenyl benzimidazole fluorescent probe as well as preparation method and application thereof

A pyrenylbenzimidazole and dimethylbenzimidazole technology, which is applied in the field of pyrenylbenzimidazole fluorescent probes and their preparation, and can solve the problem that heparin colorimetric/fluorescence dual-mode detection and fluorescent probes cannot be realized. Difficulty in synthesis, low sensitivity and other problems, to achieve the effect of easy separation and purification, improved sensitivity and fast response rate

Active Publication Date: 2021-08-10
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

Method used

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  • Pyrenyl benzimidazole fluorescent probe as well as preparation method and application thereof
  • Pyrenyl benzimidazole fluorescent probe as well as preparation method and application thereof
  • Pyrenyl benzimidazole fluorescent probe as well as preparation method and application thereof

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Experimental program
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Effect test

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 with Figure 5 As shown, with the increase of the concentration of heparin (0-8μg / mL), the absorbance of PYNN at 280nm and 370nm gr...

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Abstract

The invention provides a pyrenyl benzimidazole fluorescent probe and a preparation method and application thereof. The pyrenyl benzimidazole fluorescent probe is of a structure shown in the formula (I), and the preparation process of the pyrenyl benzimidazole fluorescent probe comprises the following steps: (1) adding 1,2-dimethyl benzimidazole and (3-bromopropyl)dimethyl ammonium bromide into acetonitrile, conducting heating reflux, and after the reaction is completed, conducting separation to obtain a compound A; and (2) heating and refluxing the compound A and 1-pyrenecarboxaldehyde in ethanol, and conducting separating and purifying to obtain the fluorescent probe with the structure as shown in the formula (I). The fluorescent probe disclosed by the invention can be used for detecting heparin, and has the characteristics of simplicity in synthesis, good water solubility, long light-emitting 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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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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