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Amphipathic polysaccharide/polypeptide block polymer containing azobenzene group and preparation method and application of block polymer

An amphiphilic polysaccharide and block polymer technology, which is applied in the field of amphiphilic polysaccharide/polypeptide block polymer and its preparation, can solve problems such as no research reports containing azobenzene, and achieve excellent biocompatibility The effect of high stability and biodegradability, excellent performance and mild preparation conditions

Active Publication Date: 2013-07-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there is no research report on this type of block polymer containing azobenzene and its light-controlled drug release.

Method used

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  • Amphipathic polysaccharide/polypeptide block polymer containing azobenzene group and preparation method and application of block polymer
  • Amphipathic polysaccharide/polypeptide block polymer containing azobenzene group and preparation method and application of block polymer
  • Amphipathic polysaccharide/polypeptide block polymer containing azobenzene group and preparation method and application of block polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (1) Under the protection of argon, add 10.40g of γ-2-chloroethyl-L-glutamate and 3.60g of trimeric phosgene into a three-necked round-bottomed flask containing 100mL of tetrahydrofuran, react at 50°C for 1 hour, and then depressurize at 30°C THF was distilled off to obtain an oily substance; 150 mL of ethyl acetate was added to the obtained oily substance, shaken up to obtain a mixed solution of ethyl acetate; the mixed solution of ethyl acetate was washed twice with 120 mL of cold 5wt% sodium bicarbonate solution, and transferred to Put it into a pear-shaped separatory funnel to separate the organic phase, dry it overnight with 15g of anhydrous magnesium sulfate, filter it, and evaporate the filtrate to dryness at 30°C, the white needles obtained are γ-2-chloroethyl-L-glutamic acid Ester ring internal acid anhydride (CELG-NCA); put 0.0172g azidoethylamine and 2.36g CELG-NCA in a reaction flask containing 10mL of anhydrous N,N-dimethylformamide at a molar ratio of 1:50, ...

Embodiment 2

[0073](1) Under the protection of argon, add 5.60g of γ-2-chloroethyl-L-glutamate and 2.40g of trimerized phosgene into a three-neck round bottom flask containing 50mL of tetrahydrofuran, react at 50°C for 1h, and then decompress at 35°C The tetrahydrofuran was distilled off to obtain an oily substance; 100 mL of ethyl acetate was added to the obtained oily substance, and shaken to obtain a mixed solution of ethyl acetate; the mixed solution of ethyl acetate was washed twice with 85 mL of cold 5wt% sodium bicarbonate solution, and transferred to Put it into a pear-shaped separating funnel to separate the organic phase, dry it overnight with 10g of anhydrous magnesium sulfate, filter it, evaporate the filtrate to dryness at 35°C, and obtain the white needle-shaped product CELG-NCA; Amine and 2.36g CELG-NCA were placed in a reaction flask containing 12mL of anhydrous N,N-dimethylformamide, argon was introduced, and the reaction was carried out at room temperature for 3 days to ob...

Embodiment 3

[0090] (1) Under the protection of argon, add 2.80g of γ-2-chloroethyl-L-glutamate and 1.20g of trimerized phosgene into a three-necked round-bottomed flask containing 100mL of tetrahydrofuran, react at 60°C for 0.5h, and then 33°C Remove tetrahydrofuran by distillation under reduced pressure to obtain an oil; add 125 mL of ethyl acetate to the obtained oil and shake well to obtain a mixed solution of ethyl acetate; wash the mixed solution of ethyl acetate twice with 100 mL of cold 5wt% sodium bicarbonate solution , transferred to a pear-shaped separating funnel to separate the organic phase, dried overnight with 12.5g of anhydrous magnesium sulfate and filtered, and evaporated the filtrate at 30°C to obtain the white needle-shaped product CELG-NCA; 0.0044g Azideethylamine and 2.36g CELG-NCA were placed in a reaction flask containing 15mL of anhydrous N,N-dimethylformamide, argon gas was passed through, and the reaction solution was obtained at room temperature for 3 days; Pre...

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Abstract

The invention discloses an amphipathic polysaccharide / polypeptide block polymer containing azobenzene group and preparation method and application of the block polymer. The amphipathic polysaccharide / polypeptide block polymer containing azobenzene group is prepared through click chemistry reaction path by using glucan as a hydrophilic chain segment and using poly-L-glutamate as a hydrophobic chain segment. The contained glucan chain segment is a water-soluble natural polysaccharide with good biocompatibility and biodegradability, the contained poly-L-glutamate chain segment is of a proteoid structure and has good biocompatibility and biodegradability. The preparation condition is mild, efficient and practical, the prepared amphipathic block polymer containing azobenzene pendant group has a capability of forming nano-micelle in the water solution; and meanwhile, the formed micelle has an ultraviolet response capability and can be used as novel drug carrier with excellent performance and light-operated drug release function.

Description

technical field [0001] The invention belongs to the field of functional polymer materials, in particular to an amphiphilic polysaccharide / polypeptide block polymer containing an azophenyl group and its preparation method and application. Background technique [0002] Azobenzene is a common functional group capable of responding to ultraviolet and visible light, and its molecular conformation has two isomers, cis and trans. Under the irradiation of ultraviolet light with a specific wavelength, the trans-configuration of azobenzene will change to the cis-configuration; and under the action of visible light, the cis-configuration can return to the trans-configuration. Therefore, azobenzene can be used as a photosensitive structure to construct different photoresponsive functional materials. Among them, the introduction of azophenyl groups into polymer segments can endow polymer materials with unique photoresponsive properties under certain conditions. At present, this type of...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08B37/02C08G69/48A61K47/42
Inventor 杨惠康张黎明
Owner SUN YAT SEN UNIV
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