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Copolymer, glucose sensitive micelle, glucose sensitive medicine-carrying micelle and preparation method thereof

A technology of glucose-sensitive and drug-loaded micelles, which is applied in the field of glucose-sensitive materials, can solve problems such as limitations in the field of bioavailability of glucose-sensitive materials, and achieve good biodegradability and good biocompatibility

Active Publication Date: 2012-03-28
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above glucose-sensitive materials are sensitive to glucose concentration, but poly-N-isopropylacrylamide, acrylic acid and 2-(N,N-dimethylamino)ethyl methacrylate are all non-biodegradable materials. The resulting glucose-sensitive materials are greatly limited in the field of bioavailability

Method used

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  • Copolymer, glucose sensitive micelle, glucose sensitive medicine-carrying micelle and preparation method thereof
  • Copolymer, glucose sensitive micelle, glucose sensitive medicine-carrying micelle and preparation method thereof
  • Copolymer, glucose sensitive micelle, glucose sensitive medicine-carrying micelle and preparation method thereof

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preparation example Construction

[0047] The present invention also provides a kind of preparation method of copolymer, comprises the following steps:

[0048] γ-benzyl-L-glutamate-N-internal carboxylic acid anhydride undergoes ring-opening polymerization under the initiation of amino-terminated polyethylene glycol monomethyl ether hydrochloride to obtain poly(ethylene glycol monomethyl ether )-b-poly(γ-benzyl-L-glutamate);

[0049] The poly(ethylene glycol monomethyl ether)-b-poly(γ-benzyl-L-glutamate) is deprotected to obtain poly(ethylene glycol monomethyl ether)-b-poly(L- glutamic acid);

[0050] Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide carries out activation reaction, then adds 3-aminophenylboronic acid and carries out condensation reaction, obtains the copolymer with formula (1) structure:

[0051]

[0052] Wherein, m is the degree of polymerization, 55≤m≤250; n is the degree of polymerization, 30≤n≤300; i and j are relative molar numbers, 0.1≤j / (i+j)...

Embodiment 1

[0097] After 25g of polyethylene glycol monomethyl ether with a molecular weight of 5000 was azeotroped with toluene to remove water, it was dissolved in 150mL of anhydrous dichloromethane, and 3.5mL of triethylamine was added at 0°C under anhydrous conditions, and 8mL of formaldehyde was added dropwise. Methylsulfonyl chloride and methanesulfonyl chloride were reacted at 0°C for 2 hours after the addition of methanesulfonyl chloride, returned to 25°C, and continued to react for 48 hours under stirring with a stirrer. , Vacuum drying at 25°C for 24h to obtain polyethylene glycol monomethyl ether methanesulfonate.

[0098] Dissolve 3g of polyethylene glycol monomethyl ether methanesulfonate and 1g of ammonium chloride in 80mL of ammonia water with a mass concentration of 25%, and react at 25°C for 72h. After the reaction, extract the aminated product with dichloromethane. Polyethylene glycol monomethyl ether, and washed with 4% sodium chloride aqueous solution by mass percentag...

Embodiment 2

[0100] Add 0.5 g (0.1 mmol) of the amino-terminated polyethylene glycol monomethyl ether hydrochloride (mPEG-NH2HCl) prepared in Example 1 to 3 reaction flasks under anhydrous conditions, and use toluene to azeotropically remove water and use Anhydrous N, N-dimethylformamide was dissolved to obtain amino-terminated polyethylene glycol monomethyl ether hydrochloride solution; 3.948g (15mmol), 5.791g (22mmol) and 6.581g (25mmol) Methyl-L-glutamate-N-internal carboxylic acid anhydride (BLG-NCA) was dissolved with anhydrous N,N-dimethylformamide, and added to the amino-terminated polyethylene glycol monomethyl ether hydrochloride In the salt solution, react for 72h at 25°C under the condition of stirring with a stirrer. After the reaction is over, pour the solution into diethyl ether whose volume is 10 times that of the solvent to settle, filter, wash, and vacuum-dry at 25°C for 24h to obtain poly(ethyl ether) respectively. Glycol monomethyl ether)-b-poly(γ-benzyl-L-glutamate) (mP...

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Abstract

The invention provides a copolymer with a structure of a formula (I), a preparation method thereof, glucose sensitive micelle containing the same, glucose sensitive medicine-carrying micelle containing the same and a preparation method of the glucose sensitive medicine-carrying micelle. The copolymer provided by the invention comprises a polyethylene glycol monomethyl ether hydrophilic chain segment and a polyglutamic acid hydrophobic chain segment, wherein the polyglutamic acid hydrophobic chain segment takes polyglutamic acid as a main chain and the branch chain contains phenylboric acid groups. In the copolymer, both polyethylene glycol monomethyl ether and the polyglutamic acid have good biocompatibility, the polyglutamic acid has good biodegradability, the carboxyl group has pH sensitivity, and the phenylboric acid group has glucose sensitivity. The copolymer provided by the invention has good biocompatibility, biodegradability, glucose sensitivity and pH sensitivity.

Description

technical field [0001] The invention belongs to the technical field of glucose-sensitive materials, and in particular relates to a copolymer, glucose-sensitive micelles, glucose-sensitive drug-loaded micelles and a preparation method thereof. Background technique [0002] Diabetes is currently one of the three major diseases that endanger human health. Clinically, insulin injections are generally used for drug administration. However, for diabetic patients, injecting insulin several times a day is not only troublesome, but also causes skin redness, swelling, itching, induration, infection, etc., and even serious side effects such as subcutaneous fat atrophy or fibrosis hyperplasia. Smart materials are a class of polymer materials that can respond to external environmental stimuli, such as temperature, pH, ion concentration, glucose, etc. The self-regulating drug delivery system combined with glucose-sensitive materials can reduce the side effects of frequent insulin injecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/48C08G69/10C08J3/07A61K47/34
Inventor 汤朝晖赵丽丁建勋肖春生何盼陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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