Functional organic silicon resin for protein adsorption and light-operated desorption and preparation method of functional organic silicon resin

Abstract

The invention belongs to the technical field of functional polymer materials and biology, and particularly relates to functional organic silicon resin for protein adsorption and light-operated desorption and a preparation method of the functional organic silicon resin. A quaternary ammonium group and a photosensitive coumarin group are introduced into organic silicon resin; protein molecules withthe isoelectric point smaller than 7.4 are adsorbed to the surface of the functional organic silicon resin through electrostatic interaction, coumarin photosensitive groups are dissociated after irradiation of a 410 nm light source, the charge property of the surface of the organic silicon resin is reversed, and the protein molecules are in a desorption state. The preparation method of the functional organic silicon resin is simple in synthesis process; the preparation method is simple, reaction conditions are mild, operability is high, the obtained functional organic silicon resin has good biocompatibility, photoresponsiveness and light-operated protein molecule desorption capacity, the desorption behavior of protein molecules can be accurately regulated and controlled by adjusting the illumination position and the illumination time, and important application value is achieved.

Description

technical field

[0001] The invention relates to a functional silicone resin capable of adsorbing and light-controlled desorbing proteins and a preparation method thereof, belonging to the fields of functional polymer materials and biotechnology. Background technique

[0002] The immobilization and release technology of biomacromolecules has very important application value in the fields of separation and purification of biomolecules, antibody and antigen molecular screening, and protein chips. Biomacromolecules are complex in structure, prone to property changes, and easy to lose biological activity. Therefore, designing and preparing suitable carrier materials is one of the important challenges in this field.

[0003] Silicone materials with Si-O-Si as the main chain structure and silicon atoms connected to organic groups have excellent high and low temperature resistance, weather resistance and aging resistance and physiological inertness, and are good carriers for biopoly...

Examples

Embodiment 1

[0088] A method for preparing a functional silicone resin for adsorption and light-controlled desorption of protein molecules, comprising the following steps:

[0089] (1) 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) was dissolved in 1,4-dioxane (120mL), and selenium dioxide was added to the above solution (3.33g, 30mmol). The reaction mixture was stirred and heated to reflux for 24h. After filtration, it was concentrated under reduced pressure to obtain a brown oil, which was dissolved in methanol (130 mL), and sodium borohydride (380 mg, 10 mmol) was added. The solution was stirred at room temperature for 4 h. The resulting suspension was carefully hydrolyzed with 1M HCl solution (20 mL), and after dilution with water, the resulting solution was extracted three times with dichloromethane (20 mL). The organic phase was washed three times with water (30 mL), saturated sodium bicarbonate solution (30 mL) and water (30 mL), respectively, and dried over anhydrous magnes...

Embodiment 2

[0099] A method for preparing a functional silicone resin for adsorption and light-controlled desorption of protein molecules, comprising the following steps:

[0100] (1) 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) was dissolved in 120mL1,4-dioxane, and selenium dioxide (2.22g ,20mmol). The reaction mixture was stirred and heated to reflux for 72h. After filtration and concentration under reduced pressure, the obtained brown oil was dissolved in methanol (130 mL), and sodium borohydride (380 mg, 10 mmol) was added. The solution was stirred at room temperature for 4 h. The resulting suspension was carefully hydrolyzed with 1M HCl solution (20 mL), and after dilution with water, the resulting solution was extracted three times with dichloromethane (20 mL). The organic phase was washed three times with water (30 mL), saturated sodium bicarbonate solution (30 mL) and water (30 mL), respectively, and dried over anhydrous magnesium sulfate. After suction filtration, sol...

Embodiment 3

[0107] A method for preparing a functional silicone resin for adsorption and light-controlled desorption of protein molecules, comprising the following steps:

[0108] (1) 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) was dissolved in 120mL1,4-dioxane, and selenium dioxide (3.33g ,30mmol). The reaction mixture was heated to reflux under stirring for 48h. After filtration and concentration under reduced pressure, the obtained brown oil was dissolved in methanol (130 mL), and sodium borohydride (380 mg, 10 mmol) was added. The solution was stirred at room temperature for 4 h. The resulting suspension was carefully hydrolyzed with 1M HCl solution (20 mL), and after dilution with water, the resulting solution was extracted three times with dichloromethane (20 mL). The organic phase was washed three times with water (30 mL), saturated sodium bicarbonate solution (30 mL) and water (30 mL), respectively, and dried over anhydrous magnesium sulfate. After suction filtration, ...

technical field

[0001] The invention relates to a functional silicone resin capable of adsorbing and light-controlled desorbing proteins and a preparation method thereof, belonging to the fields of functional polymer materials and biotechnology. Background technique

[0002] The immobilization and release technology of biomacromolecules has very important application value in the fields of separation and purification of biomolecules, antibody and antigen molecular screening, and protein chips. Biomacromolecules are complex in structure, prone to property changes, and easy to lose biological activity. Therefore, designing and preparing suitable carrier materials is one of the important challenges in this field.

[0003] Silicone materials with Si-O-Si as the main chain structure and silicon atoms connected to organic groups have excellent high and low temperature resistance, weather resistance and aging resistance and physiological inertness, and are good carriers for biopoly...

Examples

Embodiment 1

[0088] A method for preparing a functional silicone resin for adsorption and light-controlled desorption of protein molecules, comprising the following steps:

[0089] (1) 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) was dissolved in 1,4-dioxane (120mL), and selenium dioxide was added to the above solution (3.33g, 30mmol). The reaction mixture was stirred and heated to reflux for 24h. After filtration, it was concentrated under reduced pressure to obtain a brown oil, which was dissolved in methanol (130 mL), and sodium borohydride (380 mg, 10 mmol) was added. The solution was stirred at room temperature for 4 h. The resulting suspension was carefully hydrolyzed with 1M HCl solution (20 mL), and after dilution with water, the resulting solution was extracted three times with dichloromethane (20 mL). The organic phase was washed three times with water (30 mL), saturated sodium bicarbonate solution (30 mL) and water (30 mL), respectively, and dried over anhydrous magnes...

Embodiment 2

[0099] A method for preparing a functional silicone resin for adsorption and light-controlled desorption of protein molecules, comprising the following steps:

[0100] (1) 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) was dissolved in 120mL1,4-dioxane, and selenium dioxide (2.22g ,20mmol). The reaction mixture was stirred and heated to reflux for 72h. After filtration and concentration under reduced pressure, the obtained brown oil was dissolved in methanol (130 mL), and sodium borohydride (380 mg, 10 mmol) was added. The solution was stirred at room temperature for 4 h. The resulting suspension was carefully hydrolyzed with 1M HCl solution (20 mL), and after dilution with water, the resulting solution was extracted three times with dichloromethane (20 mL). The organic phase was washed three times with water (30 mL), saturated sodium bicarbonate solution (30 mL) and water (30 mL), respectively, and dried over anhydrous magnesium sulfate. After suction filtration, sol...

Embodiment 3

[0107] A method for preparing a functional silicone resin for adsorption and light-controlled desorption of protein molecules, comprising the following steps:

[0108] (1) 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) was dissolved in 120mL1,4-dioxane, and selenium dioxide (3.33g ,30mmol). The reaction mixture was heated to reflux under stirring for 48h. After filtration and concentration under reduced pressure, the obtained brown oil was dissolved in methanol (130 mL), and sodium borohydride (380 mg, 10 mmol) was added. The solution was stirred at room temperature for 4 h. The resulting suspension was carefully hydrolyzed with 1M HCl solution (20 mL), and after dilution with water, the resulting solution was extracted three times with dichloromethane (20 mL). The organic phase was washed three times with water (30 mL), saturated sodium bicarbonate solution (30 mL) and water (30 mL), respectively, and dried over anhydrous magnesium sulfate. After suction filtration, ...

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