A kind of acrylamidophenylboronic acid polymer and its preparation and application

A technology of acrylamidophenylboronic acid and aminophenylboronic acid, which is applied in the application field of small molecules or glycoproteins, can solve the problems of boronic acid group recognition and enhancement of glycoproteins, and achieves easy separation and purification, moderate degree of polymerization, and simple synthesis steps Effect

Active Publication Date: 2019-07-23
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The surface of the spherical polymer synthesized by the above method did not introduce amino groups, and did not enhance the recognition of glycoproteins by boronic acid groups.

Method used

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  • A kind of acrylamidophenylboronic acid polymer and its preparation and application
  • A kind of acrylamidophenylboronic acid polymer and its preparation and application
  • A kind of acrylamidophenylboronic acid polymer and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] In a 50 mL three-necked flask, 4.5 mmol of acrylic acid was dissolved in 15 mL of dimethylformamide, followed by adding 4.5 mmol of N,N'-dicyclohexylcarbodiimide (EDC) and 4.5 mmol of N-hydroxysuccinimide (NHS) in Activated in an ice-water bath under nitrogen protection for 4 h. Weigh 1.5 mmol of 3-aminophenylboronic acid monohydrate, 3 mmol of 4-aminobenzylamine dihydrochloride and 12.5 mmol of sodium hydroxide in 15 mL of dimethylformamide / water (v / v 3:2) mixed solvent , It was quickly injected into a three-necked flask under vigorous stirring, and the reaction was continued for 12h. After the amidation was completed, 2.25 mmol of acrylic acid and 0.15 mmol of azobisisobutyronitrile were added to the solution, and heated to 70° C. for 24 h under nitrogen protection. After the reaction was completed and returned to room temperature, about 30 mL of the solution was slowly added dropwise to 1 L of acetone, stirred rapidly to obtain a precipitate, filtered with suction a...

Embodiment 2

[0050] The polymer synthesized in Example 1 was diluted with CB buffer solution (pH 9.6), and an appropriate amount of moisturizing agent and catalyst were added to prepare a spotting solution. Use a pipette gun to spot a sample at a volume of 0.5 μL per point on a silicon wafer spin-coated with a polystyrene-grafted maleic anhydride film, and place the spotted silicon wafer under the condition of 70% humidity for 20 min. Then move to 10% humidity and dry for 30min. Soak the polymer-coated silicon wafer in CBT solution (pH 9.6) for 5 minutes until all unreacted maleic anhydride is completely hydrolyzed. After taking it out, absorb the surface liquid on one side of the silicon wafer with absorbent paper. Add glycosylated hemoglobin solution (20 μL) with a concentration of 0.5-10 μg / mL to the silicon wafer, rinse the surface antigen solution with eluent after reacting for 5 minutes, and absorb the surface liquid on one side of the silicon wafer with absorbent paper. Add 20 μL o...

Embodiment 3

[0052] In a 50 mL three-necked flask, 9 mmol of acrylic acid was dissolved in 15 mL of dimethylformamide, followed by adding 4.5 mmol of N,N'-dicyclohexylcarbodiimide (EDC) and 4.5 mmol of N-hydroxysuccinimide (NHS) in Activated in an ice-water bath under nitrogen protection for 4 h. Weigh 1.5mmol of 3-aminophenylboronic acid monohydrate, 3mmol of 4-aminobenzylamine dihydrochloride and 12.5mmol of sodium hydroxide in 15ml of dimethylformamide / water (v / v 3:3) mixed solvent , It was quickly injected into a three-necked flask under vigorous stirring, and the reaction was continued for 12h. After the amidation was completed, 0.3 mmol of azobisisobutyronitrile was added to the solution, and heated to 70° C. for 24 h under the protection of nitrogen. After the reaction was completed and returned to room temperature, about 30 mL of the solution was slowly added dropwise to 1 L of acetone, stirred rapidly to obtain a precipitate, filtered with suction and washed several times with et...

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Abstract

The invention discloses acrylamide phenylboronic polymer as well as a preparation and application thereof. The acrylamide phenylboronic polymer containing carboxyl, an amino group and a phenylboronic group is quickly and conveniently prepared through a one-pot process in a mixed solvent system of water and dimethyl formamide. The preparation for the acrylamide phenylboronic polymer comprises the following steps: dissolving propenyl monomer, aminobenzene boric monomer, aminobenzylamine monomer and a cross-linking agent into a mixed solvent of water and dimethyl formamide, adding alkaline to regulate pH, and performing amidation in ice-water bath; then, adding propenyl monomer and an initiator, reacting for 6-24 hours at a temperature of 60-70 DEG C; and finally, separating and purifying to obtain the acrylamide phenylboronic polymer. A synthesis method for the acrylamide phenylboronic polymer is simple and easy to implement, and is low in cost; and the prepared polymer is uniform in molecular weight distribution, and can be used for identifying a micromolecule or glycoprotein with a 1,2-cis-diol structure.

Description

technical field [0001] The invention belongs to the technical field of polymer materials and analysis, and relates to an acrylamidophenylboronic acid polymer, a preparation method thereof, and an application in identifying small molecules or glycoproteins of 1,2-cis-diol structure. Background technique [0002] The concentration of glycosylated hemoglobin in human blood is not affected by external conditions such as diet and hormones, and can reflect the blood sugar control level of the human body within 2 to 3 months. It is a world-recognized gold indicator for diabetes detection. The commonly used methods for detecting glycosylated hemoglobin include ion exchange method, boronic acid affinity method, immunoagglutination method and enzymatic method. Among them, the boronic acid affinity method has the advantages of being not affected by temperature, pH and hemoglobin variants, and has strong specificity, so it is widely used. [0003] The boronic acid affinity is based on ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/06C08F230/06C08F220/60G01N33/72G01N33/66
CPCC08F220/06C08F220/60C08F230/06G01N33/66G01N33/723G01N2800/042
Inventor 高云华李昊
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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