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Polyethylene glycol-polybeta-aminovite segmented copolymer and preparation method thereof

A technology of block copolymer and polyethylene glycol, which is applied in the field of poly-β-urethane, can solve the problems of high cost of poly-β-urethane, few types of secondary amines, and high price, and achieve strong variability and low cost. Low, highly adjustable effect

Inactive Publication Date: 2012-11-21
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

Due to the small number of secondary amines and the high price, the cost of preparing poly-β-urethane is high

Method used

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  • Polyethylene glycol-polybeta-aminovite segmented copolymer and preparation method thereof
  • Polyethylene glycol-polybeta-aminovite segmented copolymer and preparation method thereof
  • Polyethylene glycol-polybeta-aminovite segmented copolymer and preparation method thereof

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[0044] The present invention also provides a kind of preparation method of polyethylene glycol-poly β-urethane block copolymer, comprises the following steps:

[0045] The compound with the structure of formula (II), the primary amine and the compound with the structure of formula (III) undergo Michael addition reaction in an organic solvent to obtain polyethylene glycol-polyβ-amine as shown in formula (I) Ester block copolymers;

[0046]

[0047]

[0048] Among them, R 1 Independently selected from C3~C15 alkyl group, substituted C3~C15 alkyl group, C3~C15 alkenyl group, C3~C15 alkyne group, C6~C15 aryl group and C3~C15 heterocyclic group one or more;

[0049] R 2 It is a C2~C10 alkylene group, a substituted C2~C10 alkylene group, a C2~C10 alkenylene group, a C2~C10 alkynylene group or -R 4 -S-S-R 5 -; R 4 C1~C5 alkylene, R 5 A C1~C5 alkylene group;

[0050] R 3 It is hydrogen, C1~C8 alkyl group, C3~C8 alkenyl group or C3~C8 alkyne group;

[0051] n and m are ...

Embodiment 1

[0061] In a dry reaction bottle, add 0.5mmol of methoxypolyethylene glycol acrylate with a number average molecular weight of 2000Da, 5mmol of n-propylamine, 5mmol of ethylene glycol diacrylate and 5mL of anhydrous chloroform, and seal the reaction at 60°C for 72 hours. After receiving, settle with n-hexane, collect the solid, and dry it under vacuum at room temperature to obtain the polyethylene glycol-poly-β-urethane block copolymer represented by formula (I).

[0062] Using deuterated chloroform as a solvent, the polyethylene glycol-poly β-urethane block copolymer is subjected to nuclear magnetic resonance analysis, and the structure shows that the number average of the polyethylene glycol-poly β-urethane block copolymer is The molecular weight is 4.3×10 3 , where m=10, n=44, R 1 is n-propyl, R 2 is ethyl, R 3 For methyl. The yield of the reaction was 86.9%.

Embodiment 2

[0064] In a dry reaction bottle, add 0.5mmol of methoxypolyethylene glycol acrylate with a number average molecular weight of 2000Da, 5mmol of n-propylamine, 5mmol of propylene glycol diacrylate and 5mL of anhydrous chloroform, and seal the reaction at 60°C for 72 hours. After the reaction is accepted, Settling with n-hexane, collecting the solid, and vacuum drying at room temperature to obtain the polyethylene glycol-poly-β-urethane block copolymer represented by formula (I).

[0065] Using deuterated chloroform as a solvent, the polyethylene glycol-poly β-urethane block copolymer is subjected to nuclear magnetic resonance analysis, and the structure shows that the number average of the polyethylene glycol-poly β-urethane block copolymer is The molecular weight is 4.4×10 3 , where m=10, n=44, R 1 is n-propyl, R 2 is propyl, R 3 For methyl. The yield of the reaction was 83.9%.

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Abstract

The invention provides a polyethylene glycol-polybeta-aminovite segmented copolymer. A preparation method of the polyethylene glycol-polybeta-aminovite segmented copolymer includes: subjecting a compound having a structure as formula (II), primary amine, and a compound having a structure as formula (III) to Michael addition reaction in organic solvent so as to obtain the polyethylene glycol-polybeta-aminovite segmented copolymer as formula (I). The polyethylene glycol-polybeta-aminovite segmented copolymer prepared by the method is low in cost, high in side chain variability and high in adjustability of response area of pH. Due to hydrophilicity of polyethylene glycol chains and pH response hydrophobicity of the polybeta-aminovite chains, self-assembly particles of the segmented copolymer can be formed in solution. By using the polyethylene glycol-polybeta-aminovite segmented copolymer as a drug carrier, pH response fast releasing of the drug can be achieved.

Description

technical field [0001] The invention relates to the field of poly-β-urethane, in particular to a polyethylene glycol-poly-β-urethane block copolymer and a preparation method thereof. Background technique [0002] The internal environment of tumor cells is mainly manifested as "three lows and one high", namely: low oxygen, low sugar, low pH value and high glutathione concentration, especially low pH value, pH value of late endosomes and lysosomes Can be as low as 5.0 (Advanced Functional Materials 19(22):3580-3589). Therefore, designing a drug-loading system that can exist stably under normal physiological conditions, and can quickly respond to the pH value signal after reaching the tumor tissue or tumor cells to achieve rapid release of the drug is essential for the targeted delivery of anti-tumor drugs and the ability to overcome tumors. The multidrug resistance of cells is of great significance. [0003] Poly β-urethane is a kind of pH-sensitive polymer with good biocomp...

Claims

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Application Information

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IPC IPC(8): C08G73/00A61K47/34
Inventor 汤朝晖宋万通吕世贤于海洋陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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