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Water-soluble amino acid segmented copolymer, and preparation method and application thereof

A technology of block copolymers and amino acids, applied in the field of polyamino acids, can solve the problems of the complexity of the preparation process, change the assembly and morphology of nano-drugs, etc. Effect

Active Publication Date: 2016-10-12
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the addition of lyoprotectants will increase the complexity of the preparation process, and may also change the assembly and morphology of nanomedicines

Method used

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  • Water-soluble amino acid segmented copolymer, and preparation method and application thereof
  • Water-soluble amino acid segmented copolymer, and preparation method and application thereof
  • Water-soluble amino acid segmented copolymer, and preparation method and application thereof

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preparation example Construction

[0081] The invention provides a method for preparing a water-soluble amino acid block copolymer, comprising: reacting a first block copolymer having a structure of formula III with ethanolamine to obtain an amino acid block copolymer having a structure of formula I;

[0082]

[0083] In formula III and formula I, R 1 selected from hydrogen, alkyl or substituted alkyl; R 2 selected from -NH- or -R 5 (CH 2 ) r NH-, where, R 5 is -O-, -OCONH-, -OCO-, -NHCOO- or -NHCO-, 1≤r≤10; R 4 Be selected from benzyl, cholesterol formyl, acetyl, cholic acid, deoxycholic acid or C4~C20 alkyl; 20≤n≤500; 5≤m≤200; in formula I, R 3 for hydrogen.

[0084]The present invention uses the first block copolymer having the structure of formula III as raw material, which includes polyaspartic acid segments with protective groups. The embodiment of the present invention provides the first block copolymer, and its preparation method is preferably as follows: a monoaminopolyethylene glycol compoun...

Embodiment 1

[0123] Add 5.00 g of a polyethylene glycol compound having a structure of formula V with a number average molecular weight of 5000 to the dry reaction flask, and remove water with 80 mL of anhydrous toluene at 130 ° C for 3 hours, and then vacuum dry the remaining toluene; the obtained solid was dissolved in 50 mL of dry N,N-dimethylformamide to obtain the first solution; 3.50 g of γ-benzyl-L-aspartic acid ester-N-internal carboxylic acid anhydride was dissolved in 40 mL of dry N,N-dimethylformamide to obtain a second solution. In a nitrogen atmosphere, the first solution and the second solution were mixed, stirred and reacted at room temperature under nitrogen protection for 48 h; then the temperature was raised to 35° C., and 10 mL of acetic anhydride was added to continue the reaction for 24 h. After the reaction, most of the N,N-dimethylformamide and unreacted acetic anhydride were sucked off under reduced pressure, then settled with diethyl ether, suction filtered, and dr...

Embodiment 2

[0129] In a dry round bottom flask, add 15.0g benzyl alcohol and 33.0g carbonyldiimidazole, add 100mL anhydrous dichloromethane to dissolve, and react at room temperature for 12h. After the reaction was completed, 500 mL of ethyl acetate was added to the system for dilution, and the organic layer was washed with distilled water and saturated brine successively, and then the organic layer was washed with anhydrous MgSO 4 Let dry overnight. The organic solvent was removed under reduced pressure to finally obtain 10.0 g of Bn-CDI.

[0130] In order to obtain the macromolecular material modified by benzyloxycarbonyl, add the block copolymer with formula I-a structure, Bn-CDI (145mg) and DMAP (105mg) prepared in 1.00g embodiment 1 in the dry reaction bottle, vacuumize 12h. Then 10 mL of dry N,N-dimethylformamide was added to dissolve, and the reaction was stirred at 50° C. for 12 h under nitrogen protection. After the reaction is finished, settle with excess ether, wash, filter ...

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Abstract

The invention provides a water-soluble amino acid segmented copolymer, and a preparation method and application thereof. The amino acid segmented copolymer has the structure shown as a formula I or formula II shown as the accompanying drawing; R1 is a hydrogen, an alkyl group or a substituted alkyl group; R2 is -NH- or R5(CH2)rNH-; R3 is one or a plurality of groups of a hydrogen, a hydrophobic group and an active drug group; R4 is benzyl, cholesterol formylm, acetyl, a cholic acid group, a deoxidized cholic acid group or C4-C20 alkyl groups. The amino acid segmented copolymer is a polypeptide copolymer with excellent water solubility, and can be used in the field of delivery of biological materials such as drug. After freeze-drying, the material has a good re-dissolving effect; the defect of poor water solubility of macromolecule materials or macromolecule nanometer drug in the prior art can be overcome. The material contains the hydrophobic group through modification or is chemically bonded with drug with biological activity; the modified macromolecule material or the bonded drug can still maintain excellent water solubility and re-dissolving capability; the potential application prospect is realized in the field of biological materials.

Description

technical field [0001] The invention relates to the technical field of polyamino acids, in particular to a water-soluble amino acid block copolymer and its preparation method and application. Background technique [0002] In the past ten years, the rapid development of nano-medicine has had a profound impact on the delivery of traditional small-molecule drugs in the body. Nanomedicine refers to the use of nanotechnology to load active pharmaceutical ingredients inside nanomaterials to prepare nanoscale drugs. These nanomedicines can deliver active pharmaceutical ingredients to target positions in the body, and then release the drug to exert its activity. Wherein, the active ingredients of the medicine include anticancer drugs, anti-inflammatory drugs or antiviral drugs. Nano-carriers can improve the water solubility and in vivo stability of loaded drugs, and can release drugs slowly or controlledly at the lesion site to achieve a more durable and efficient therapeutic effec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/48C08G69/40A61K47/48A61K31/352A61P35/00
CPCA61K31/352C08G69/40C08G69/48
Inventor 汤朝晖吕世贤于海洋马胜周卉聪陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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