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Polymer, glucose-sensitive nanogel, glucose-sensitive drug loading nanogel and preparation methods thereof

A glucose-sensitive, nano-gel technology, applied in the field of polymers, can solve the problems of poor biodegradability and biocompatibility of glucose-sensitive nano-gels, limiting applications, etc., achieve good biodegradability, facilitate rapid release, and improve curative effect Effect

Active Publication Date: 2013-11-20
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

The above-mentioned glucose-sensitive nanogels are sensitive to glucose concentration, but they are all made of non-biodegradable materials. Therefore, the obtained glucose-sensitive nanogels have poor biodegradability and biocompatibility, which greatly limits their application in glucose-sensitive nanogels. Application in the field of self-adjusting and controlled release of insulin

Method used

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  • Polymer, glucose-sensitive nanogel, glucose-sensitive drug loading nanogel and preparation methods thereof
  • Polymer, glucose-sensitive nanogel, glucose-sensitive drug loading nanogel and preparation methods thereof
  • Polymer, glucose-sensitive nanogel, glucose-sensitive drug loading nanogel and preparation methods thereof

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preparation example Construction

[0037] The invention provides a method for preparing a polymer represented by formula (I), comprising the following steps:

[0038] reacting the polymer represented by formula (II) and 3-aminophenylboronic acid under the action of a condensing agent to obtain the polymer represented by formula (I);

[0039]

[0040]

[0041] Wherein, m is the degree of polymerization, 55≤m≤250, preferably 100≤m≤200, more preferably 110≤m≤150; n is the degree of polymerization, 20≤n≤150, preferably 30≤n≤120, more preferably Preferably 40≤n≤100; 0.05≤i / n<1, preferably 0.1≤i / n<0.7, more preferably 0.2≤i / n≤0.6.

[0042]In the present invention, the polymer represented by formula (II) is reacted with 3-aminophenylboronic acid under the action of a condensing agent to obtain the polymer represented by formula (I). In the reaction, the polymer represented by formula (II) is preferably firstly activated with a condensing agent in an organic solvent, and then reacted with 3-aminophenylboronic ac...

Embodiment 1

[0081] After 25.0 g of polyethylene glycol monomethyl ether with a molecular weight of 5000 was azeotroped to remove water with toluene, it was dissolved in 150.0 mL of anhydrous dichloromethane, and 3.5 mL of triethylamine was added at 0°C under anhydrous conditions, and added dropwise React with 8.0 mL of methanesulfonyl chloride, react at 0°C for 2 hours, return to 25°C, and continue to react for 48 hours under stirring with a stirrer. Dry under vacuum for 24 hours to obtain polyethylene glycol monomethyl ether methanesulfonate.

[0082] Dissolve 3.0 g of the above-prepared polyethylene glycol monomethyl ether methanesulfonate and 1.0 g of ammonium chloride in 80.0 mL of ammonia water with a mass concentration of 25%, and react at 25°C for 72 hours. After the reaction, the amino-terminated polyol Ethylene glycol monomethyl ether, extract the aminated polyethylene glycol monomethyl ether with dichloromethane, wash with 4% sodium chloride aqueous solution, settle ether, filte...

Embodiment 2

[0084] Add 1.041 g (0.208 mmol) of amino-terminated polyethylene glycol monomethyl ether hydrochloride (mPEG-NH 2 HCl), using toluene to azeotropically remove water and then dissolving with anhydrous N,N-dimethylformamide to obtain amino-terminated polyethylene glycol monomethyl ether hydrochloride solution.

[0085] 3.2854g (12.48mmol) of the compound (BLG-NCA) with the structure of the formula (III) and 0.794g (4.16mmol) of the compound (CELG-NCA) with the structure of the formula (IV) were treated with anhydrous N,N-dimethyl Formamide was dissolved and added to the amino-terminated polyethylene glycol monomethyl ether hydrochloride solution, and the reaction was carried out at 25°C under stirring with a stirrer. The reaction time was 72 hours. After the reaction was completed, the solution was poured into the volume Sedimentation in diethyl ether 10 times the amount of the solvent, filtration, washing, and vacuum drying at 25°C for 24 hours to obtain a benzyl alcohol-protec...

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Abstract

The present invention provides a polymer represented by a formula (I), wherein the preparation method comprises that a polymer represented by a formula (II) and 3-aminobenzeneboronic acid are subjected to a reaction under a condensation agent effect to obtain the polymer represented by the formula (I). The present invention further provides a glucose-sensitive nano-gel, which is prepared by cross-linking the polymer represented by the formula (I) under a quaternary ammonium salt effect. The glucose-sensitive nanogel and a drug are combined to obtain a glucose-sensitive drug loading nanogel, wherein the glucose-sensitive drug loading nanogel has characteristics of good biocompatibility and good biodegradability, can be degraded in organisms while does not produce harm on organisms, and can be adopted as a carrier material to rapid respond to change in glucose concentration so as to easily achieve rapid drug release under a high glucose concentration and improve drug treatment efficacy.

Description

technical field [0001] The invention relates to the field of macromolecules, in particular to a polymer, a glucose-sensitive nanogel, a glucose-sensitive drug-loaded nanogel and a preparation method thereof. Background technique [0002] Diabetes has become one of the three major killers of human health after tumors and cardiovascular diseases, and the number of diabetic patients has shown a sharp increase in recent years, and the treatment of diabetes is imminent. Diabetes is an endogenous disease. It is a disease in which blood sugar rises and contains sugar in the urine due to insufficient insulin secretion in the body. For the treatment of diabetes, insulin injections are generally used clinically. Although injecting insulin can quickly achieve the goal of lowering blood sugar, injecting insulin several times a day is not only troublesome, but also causes serious side effects such as skin redness, itching, induration, and infection, which brings great physical and mental...

Claims

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Application Information

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IPC IPC(8): C08G69/48C08G69/40C08J3/24C08J3/075C08L77/02C08K5/372A61K47/34A61K9/06A61K38/28A61P3/10
Inventor 陈学思赵丽丁建勋肖春生庄秀丽
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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