Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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

A technology of benzimidazoles and dimethylbenzimidazoles, applied in the field of tetrastyrylbenzimidazole fluorescent probes and their preparation, can solve the problems of poor selectivity, difficult synthesis of HSA fluorescent probes, and low sensitivity , to achieve the effects of fast response rate, easy separation and purification, and improved sensitivity

Pending Publication Date: 2022-07-15
HEBEI UNIVERSITY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a tetrastyrylbenzimidazole fluorescent probe and its preparation method and application, to solve the problems of existing HSA fluorescent probes such as difficult synthesis, low sensitivity and poor selectivity

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Tetraphenylethylene benzimidazole fluorescent probe as well as preparation method and application thereof
  • Tetraphenylethylene benzimidazole fluorescent probe as well as preparation method and application thereof
  • Tetraphenylethylene benzimidazole fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The synthesis of embodiment 1TPNN

[0042] (1) Synthesis of Compound A

[0043]

[0044] 0.44g (3mmol) of 1,2-dimethylbenzimidazole, 0.78g (3mmol) of (3-bromopropyl)dimethylammonium bromide, 25mL of acetonitrile were added to a 50mL round-bottomed flask, and the stirring was turned on and heated. To 90 ℃, reflux reaction for 8h. Then, the reaction solution was cooled to room temperature, the reaction solution was concentrated under reduced pressure to 1 / 2 of the original volume, a white solid was precipitated, and the compound A was obtained by suction filtration under reduced pressure, which was subjected to the next reaction.

[0045] (2) Synthesis of fluorescent probe TPNN

[0046]

[0047] Into a 100 mL round-bottomed flask was added 0.36 g (1 mmol) of 1,1,2-triphenyl-2-(4-carbaldehyde phenyl)ethylene, 0.41 g (1 mmol) of compound A, and 0.17 g (2 mmol) of piperazine, 80 mL of N,N-dimethylformamide was turned on to stir, heated to 90° C., and the reaction wa...

Embodiment 2

[0050] Example 2 AIE properties of TPNN

[0051]The DMSO stock solution (concentration of 500 μM) of TPNN prepared in Example 1 was added to a 2 mL EP tube, and then 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 solution volume was 1 mL, and the final concentration of TPNN was 5 μM. The above solution was placed at room temperature for 10min and its fluorescence spectrum (excitation wavelength 370nm) was measured.

[0052] image 3 (A) is the change of the fluorescence spectrum of TPNN with the volume fraction of toluene in the mixed solvent of toluene-tetrahydrofuran; (B) is the change trend of the fluorescence intensity of TPNN at 530 nm with the volume fraction of toluene. like image 3 As shown, tetrahydrofuran and toluene are used as benign and poor solvents for TPNN, respectively. As the volume fraction of toluene in the toluene-tetrahydrofuran mixed solution increases, ...

Embodiment 3

[0053] Example 3 Spectral Responsiveness of TPNN to HSA

[0054] The DMSO stock solution (concentration of 500 μM) of TPNN prepared in Example 1 was added to a 2 mL EP tube, and then deionized water, PBS buffer solution (pH 7, 200 mM) and different volumes of HSA stock solution (concentration) were added to the tube sequentially. 1 mg / mL). The total volume of the solution is 1 mL, the final concentration of TPNN is 5 μM, the final concentration of PBS buffer solution is 10 mM, and the final concentration of HSA is 0-500 μg / mL.

[0055] Figure 4 (A) is the fluorescence spectrum of TPNN after adding 0-500 μg / mL HSA; Figure 4 (B) is the linear relationship between the fluorescence intensity of TPNN at 530 nm and the concentration of HSA after adding 0-60 μg / mL HSA. like Figure 4 (A) and Figure 4 As shown in (B), with the increase of HSA concentration, the fluorescence of TPNN gradually increased, showing a highly sensitive response to HSA. The fluorescence intensity of ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a tetraphenylethylene benzimidazole fluorescent probe and a preparation method and application thereof.The fluorescent probe is of a structure shown in the formula (I), and the preparation method of the fluorescent probe comprises the following steps that 1, 1, 2-dimethyl benzimidazole and (3-bromopropyl) dimethyl ammonium bromide are added into acetonitrile, heating reflux is conducted, and after the reaction is completed, separation is conducted to obtain a compound A; and (2) heating and refluxing the compound A and 1, 1, 2-triphenyl-2-(4-formylbenzene) ethylene in N, N-dimethylformamide, and separating and purifying to obtain the fluorescent probe with the structure as shown in the formula (I). The fluorescent probe disclosed by the invention has the advantages of simplicity in synthesis, high sensitivity, good selectivity, high response rate, strong stability and the like. The kit can accurately measure the concentration of serum albumin, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a tetrastyryl benzimidazole fluorescent probe and a preparation method and application thereof. Background technique [0002] Human Serum Albumin (HSA, Human Serum Albumin) is a heart-shaped single-chain protein composed of 585 amino acids with a molecular weight of about 66.5kDa. It is the most abundant protein in plasma, accounting for more than 50% of the total plasma protein. . After HSA is synthesized in hepatocytes, processed by the rough endoplasmic reticulum, it is transported to the Golgi apparatus for modification, and then mature albumin is formed and released into the blood. HSA has strong ligand binding ability and is the main transporter of many endogenous substances and exogenous drugs (such as hormones, fatty acids, drugs and other biologically active small molecules). In addition, HSA also plays an important role in maintaining plasma c...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D235/08C09K11/06G01N21/64
CPCC07D235/08C09K11/06G01N21/6428C09K2211/1044C09K2211/1007
Inventor 白洁聂海亮闫宏远梁晓萌杨学萍
Owner HEBEI UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com