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Coronene derivative probe and preparation method thereof, and protein detection method based on coronene derivative probe and aptamer

A nucleic acid aptamer and protein detection technology, applied in the field of preparation, hexacene derivative probes, and protein detection based on hexacene derivative probes and nucleic acid aptamers, can solve the problem of high cost and sensitivity Low, cumbersome steps and other issues

Active Publication Date: 2014-08-20
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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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 hexacene derivative probe, a preparation method, and a hexacene derivative probe based on a hexacene derivative probe and nucleic acid in order to solve the defects of low sensitivity and cumbersome steps and high cost of existing protein detection methods. Protein detection method of aptamer

Method used

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  • Coronene derivative probe and preparation method thereof, and protein detection method based on coronene derivative probe and aptamer
  • Coronene derivative probe and preparation method thereof, and protein detection method based on coronene derivative probe and aptamer
  • Coronene derivative probe and preparation method thereof, and protein detection method based on coronene derivative probe and aptamer

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preparation example Construction

[0037] The present invention also provides a preparation method of a hexabenzocene derivative probe, comprising:

[0038] Step 1: Add perylene, N-ethylmaleimide, tetrachlorobenzoquinone and p-methoxyphenol in the reaction vessel, and react at 230-280°C for 4-12 hours under the protection of nitrogen, and react to In the later stage, the solution becomes viscous, and then dimethylformamide is added, reacted for 30-60 minutes, filtered, washed, and dried to obtain orange powdery solid compound 1, and the molar ratio of perylene and p-methoxyphenol is preferably 2 : 1, the mol ratio of described perylene, N-ethylmaleimide, chloranil and p-methoxyphenol is preferably (2.4-4.8): (10-80): (4-20) : (1.2-2.4), the amount of the solvent dimethylformamide is not particularly limited, as long as it can dissolve the reaction mixture;

[0039] Step 2: Mix compound 1, potassium hydroxide and isopropanol obtained in step 1, react at 85-100°C for 12-24 hours, add excess water, adjust pH to 3...

Embodiment 1

[0051] Step 1: Add 2.4mmol perylene, 40mmol N-ethylmaleimide, 9mmol tetrachlorobenzoquinone, 1.2mmol p-methoxyphenol to a 50mL single-necked bottle, and react at 250°C for 6h under nitrogen protection, then add 30mL di Methylformamide was refluxed for 30 minutes, filtered, washed with methanol and ether, and dried to obtain an orange powdery solid compound 1;

[0052] Step 2: Add 0.2mmol compound 1, 0.3gKOH, and 30mL isopropanol to a 100mL single-necked bottle, react at 95°C for 12 hours, add 30mL water, add dilute hydrochloric acid to adjust the pH to 4, filter, wash with water and ethanol, and vacuum dry , to obtain red solid compound 2;

[0053] Step 3: Add 0.5mmol of compound 2, 1gKOH, and 30mL of water into a 100mL two-necked flask, react at 90°C for 2h, cool to room temperature, adjust the pH to 8, add 0.2g of tetra-n-octylammonium bromide and 2mL of 1,4-dibromide Butane, react at 130°C for 3 hours, cool down, add 30mL chloroform to the reaction bottle, wash the organic...

Embodiment 2

[0060] Step 1: Add 4.8mmol perylene, 80mmol N-ethylmaleimide, 20mmol tetrachlorobenzoquinone, 2.4mmol p-methoxyphenol to a 100mL single-necked bottle, react at 230°C for 4h, then add 60mL Dimethylformamide was refluxed for 60 minutes, filtered, washed with methanol and ether, and dried to obtain orange powdery solid compound 1;

[0061] Step 2: Add 0.2mmol compound 1, 0.6gKOH, and 30mL isopropanol to a 100mL single-necked bottle, react at 85°C for 24 hours, add 50mL water, add dilute hydrochloric acid to adjust the pH to 4, filter, wash with water and ethanol, and vacuum dry , to obtain red solid compound 2;

[0062] Step 3: Add 0.5mmol of compound 2, 1gKOH, and 30mL of water into a 100mL two-neck flask, react at 85°C for 6h, cool to room temperature, adjust the pH to 8, add 0.2g of tetra-n-octylammonium bromide and 2mL of 1,4-dibromide Butane, react at 100°C for 6 hours, cool, add 40mL chloroform to the reaction bottle, wash the organic layer with water and saturated NaCl aq...

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Abstract

The invention provides a coronene derivative probe and a preparation method thereof and a protein detection method based on the coronene derivative probe and aptamer. The objective of the invention is to overcome the problems of tedious operation, complex process and low sensitivity of a conventional protein detection method. The probe is 1,2,7,8-tetra-(4-trimethylamine butyloxycarbonyl)-coronene and has four charges and water solubility. The invention provides the preparation method for the coronene derivative probe. The invention further provides the protein detection method based on the coronene derivative probe and the aptamer. The protein detection method is marker-free, simple and fast and does not need covalent modification; moreover, a fluorescence enhanced signal is given out in detection, so compared with a fluorescence weakened signal, higher sensitivity is obtained.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a hexacene derivative probe, a preparation method and a protein detection method based on the hexacene derivative probe and a nucleic acid aptamer. Background technique [0002] At present, in the fields of medical diagnosis, biochemical research and environmental analysis, the most common method for detecting proteins is based on the specific interaction of antigen-antibody. However, the immune-based detection method also has its disadvantages: the screening, identification, and isolation of antibodies rely on animal and cell culture, and the detection process requires antibody immobilization and modification of signal output groups, which undoubtedly increases research work. Difficulty and requirements have increased the cost of related products. [0003] Nucleic acid aptamer is a novel nucleic acid molecule with high-efficiency recognition function that is screened th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C219/14C07C213/02G01N21/64
Inventor 于聪李永新王燕张青峰王方远陈健周会鹏
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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