Table of Materials/Methods for the Covalent Immobilization of Bioactive Factors by Photogenerated Aldehyde/Kone Groups at the Interface

A bioactive factor, covalent immobilization technology, applied in the biological field, can solve the problems of low efficiency, easy quenching of free radicals, long reaction time, etc.

Active Publication Date: 2021-08-13
ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is exactly in order to overcome the shortcoming and deficiency of existing method, and propose a kind of material surface / interface photogenerated aldehyde / ketone group covalent immobilization method and application of bioactive factor, this method realizes bioactive factor time, While the space and dose can be controlled and fixed, it avoids the disadvantages of low efficiency caused by problems such as long reaction time, additional modification, and easy quenching of free radicals in previous strategies.

Method used

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  • Table of Materials/Methods for the Covalent Immobilization of Bioactive Factors by Photogenerated Aldehyde/Kone Groups at the Interface
  • Table of Materials/Methods for the Covalent Immobilization of Bioactive Factors by Photogenerated Aldehyde/Kone Groups at the Interface
  • Table of Materials/Methods for the Covalent Immobilization of Bioactive Factors by Photogenerated Aldehyde/Kone Groups at the Interface

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Embodiment 1: Synthesis of photosensitive functional molecule 6

[0083]

[0084] Synthetic route of photosensitive functional molecule 6

[0085] (1) Synthesis of compound 1

[0086] Add vanillin (15g, 0.1mol) in a 500mL single-necked round bottom flask, dissolve it with 300mL of acetonitrile, slowly add potassium carbonate (16.35g, 1.2mol) and potassium iodide (19.62g, 1.2mol) into the flask while stirring , to prevent stirring, heated to reflux at 90°C, and reacted overnight under the protection of argon. TLC (PE:EA=1:1) detects the progress of the reaction. After the reaction is over, cool the system to room temperature, filter with suction, spin dry the filtrate, dissolve the solid in ethyl acetate, wash with water to remove soluble salts, spin dry the solid with 95% ethanol After recrystallization, after cooling and crystallization was complete, suction filtration was obtained to obtain a white solid, which was dried in an oven to obtain 20.3 g of solid, name...

Embodiment 2

[0121] Embodiment 2: Synthesis of photosensitive functional molecule 8

[0122]

[0123] Synthetic route of photosensitive functional molecule 8

[0124] (1) Synthesis of Compound 7

[0125] Add compound 6 (2g, 0.006mol), N,N-dimethyl-3-propion hydrochloride (1g, 0.01mol), carbodiimide (1.9g, 0.01mol) in 100mL round bottom flask, 4-Lutidine (1.2 g, 0.01 mol), dissolved in 50 mL of dehydrated DCM, stirred at room temperature, and reacted overnight under the protection of argon. TLC (DCM 1 mL plus three drops of MeOH) was used to detect the progress of the reaction. After the reaction, wash with water to remove water-soluble carbodiimide, and purify with silica gel chromatography column (DCM:MeOH=0.5%~1%) to obtain 1.8g of viscous liquid, namely compound 7, with a yield of 70.6%, avoiding wavelength 365nm light direct preservation.

[0126] The physicochemical parameters of compound 7 are:

[0127] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):7.78(s,1H),7.04(s,1H),6.14(s,1H),5.60(...

Embodiment 3

[0136] Example 3: Synthesis of photoresponsive functional molecule 12

[0137]

[0138] Synthetic route of photosensitive functional molecule 12

[0139] (1) Synthesis of compound 9

[0140] Add tetraethylene glycol (20 g, 0.1 mol) into a 100 mL round bottom flask, add 50 ml THF to dissolve, add 2 mL TEA, and stir under ice-bath conditions. Under the protection of argon, a THF solution of p-toluenesulfonyl chloride (1.9 g, 0.01 mol) was added dropwise. After the dropwise addition, the ice bath was removed to continue stirring, and the reaction was detected by TLC. After the reaction, the solvent was spin-dried, dissolved in dichloromethane, washed with water, and the organic phase was separated and dried over anhydrous sodium sulfate. After spin-drying, the product was purified by silica gel column chromatography, namely compound 9.

[0141] The physicochemical parameters of compound 9 are:

[0142] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):7.75(2H,d,J=8.2Hz,),7.31(2H,d,J=8Hz,...

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Abstract

The invention relates to a method for controllably immobilizing bioactive factors by light-generated aldehyde / ketone groups on the material surface / interface. The method of the present invention does not require additional chemical modification of the bioactive factor to be immobilized, does not destroy the biological activity of the bioactive factor, and can perform mild and effective covalent immobilization on the material surface / interface under the control of light at low temperature or room temperature. The method for immobilizing biologically active factors of the present invention has simple process and good repeatability, and can realize the immobilization of proteins, polypeptides, antibodies, growth factors or enzymes on the surfaces of various glasses, metals, organic polymers, etc., and is an innovation of protein immobilization methods . The present invention further relates to the application of the obtained protein immobilization material in various fields of biomedicine and tissue engineering, such as cell scaffold, in vitro diagnosis, enzyme catalysis, and protein purification.

Description

technical field [0001] The invention belongs to the field of biotechnology, and relates to a method for realizing the immobilization of at least one bioactive factor on the surface / interface of a material through a photo-generated aldehyde / ketone group strategy. Background technique [0002] In recent years, the immobilization of bioactive factors on the surface of materials has been a hot research topic. It is very important to maintain the structure and function of biologically active factors and directional immobilize them on the surface of materials with maximum performance and efficiency, which provides the necessary conditions for the application of materials in the fields of diagnostic biosensing, immunodiagnostic reagents, surgical implants and purified proteins . For example, in tissue engineering biomaterials, most of the artificially synthesized polymers are not very biocompatible due to the chemical inertness of the surface. It is necessary to modify the bioacti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/575C07C45/64C07C201/08C07C205/44C07C201/12C07C205/37C07C227/18C07C229/12C07C303/32C07C309/14C07C213/06C07C217/10C07F7/18C07D303/26C07C231/02C07C235/08C07C269/06C07C271/16C12N11/02C07K1/22
CPCC07C45/64C07C47/575C07C201/08C07C201/12C07C205/37C07C205/44C07C213/06C07C217/10C07C227/18C07C229/12C07C231/02C07C235/08C07C269/06C07C271/16C07C303/32C07C309/14C07D303/26C07K1/22C12N11/02
Inventor 包春燕明尊振蔡正伟薛源范金燕林秋宁朱麟勇
Owner ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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