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Amino acid block copolymer and preparation method and compound thereof

A technology of block copolymer and amino acid, applied in the field of amino acids, can solve the problems of difficult release, unclear structure, strong chemical bond, etc., and achieve the effect of good biocompatibility and long-lasting efficacy.

Active Publication Date: 2013-06-05
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, this method also brings new problems, such as unclear structure, difficult to distinguish the drug bound on the polymer from free or encapsulated in the carrier, and the strong chemical bond makes it difficult to release from the carrier. , thus limiting the application of polymer bonded drugs

Method used

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  • Amino acid block copolymer and preparation method and compound thereof
  • Amino acid block copolymer and preparation method and compound thereof
  • Amino acid block copolymer and preparation method and compound thereof

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preparation example Construction

[0057] The present invention also provides a preparation method of an amino acid block copolymer having a structure of formula (I), comprising:

[0058] The compound with the structure of formula (III) or formula (IV) reacts with the protected amino acid monomer in an organic solvent to obtain a compound with a protecting group;

[0059] Deprotecting the compound with a protecting group to obtain an amino acid block copolymer with a structure of formula (I); the amino acid monomer is γ-benzyl-L-glutamic acid ester-N-carboxylic acid anhydride and L-phenylalanine-N-internal carboxylic acid anhydride;

[0060]

[0061] Among them, R 1 are independently selected from hydrogen, alkyl or substituted alkyl;

[0062] R 5 is -O-, -OCONH-, -OCO-, -NHCOO- or -NHCO-;

[0063] m is the degree of polymerization, 20≤m≤500; r is the degree of polymerization, 1≤r≤10.

[0064] The R 1 Independent preferably C1~C40 alkyl or composed of sulfhydryl, sugar residue, aldehyde, carboxyl, viny...

Embodiment 1

[0099] Add 4.00g of polyethylene glycol monomethyl ether with a number average molecular weight of 5000 and a structure of formula (III) to the dry reaction bottle, and remove water by azeotropic removal with 60mL of anhydrous toluene at 130°C for 3 hours, then vacuum dry The remaining toluene; the obtained solid was dissolved in 40 mL of dry N,N-dimethylformamide to obtain the first solution; 2.10 g of γ-benzyl-L-glutamate-N-carboxylic acid anhydride was mixed with 1.53 gL-Phenylalanine-N-internal carboxylic acid anhydride was dissolved in 36 mL of dry N,N-dimethylformamide to obtain the second solution; in a nitrogen atmosphere, the first solution was mixed with the second solution, at room temperature , Stirring and reacting for 72h under nitrogen protection; after the reaction, drain N,N-dimethylformamide under reduced pressure, then dissolve the obtained solid in dichloromethane, settle with ether, filter with suction, and dry , to obtain poly compounds with protective gr...

Embodiment 2

[0103] Add 4.00g of polyethylene glycol monomethyl ether with a number average molecular weight of 5000 and a structure of formula (III) to the dry reaction bottle, and remove water by azeotropic removal with 60mL of anhydrous toluene at 130°C for 3 hours, then vacuum dry The remaining toluene; the obtained solid was dissolved in 40 mL of dry N,N-dimethylformamide to obtain the first solution; 4.20 g of γ-benzyl-L-glutamate-N-carboxylic acid anhydride was mixed with 1.53 gL-Phenylalanine-N-internal carboxylic acid anhydride was dissolved in 60 mL of dry N,N-dimethylformamide to obtain the second solution; in a nitrogen atmosphere, the first solution was mixed with the second solution, at room temperature , Stirring and reacting for 72h under nitrogen protection; after the reaction, drain N,N-dimethylformamide under reduced pressure, then dissolve the obtained solid in dichloromethane, settle with ether, filter with suction, and dry , to obtain poly compounds with protective gr...

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Abstract

The invention provides an amino acid block copolymer with a formula I or a formula II structure and preparation method of the amino acid block copolymer with the formula I or the formula II structure. The invention further provides a compound comprising the amino acid block copolymer and aqueous medium. Poly, namely, ethylene glycol in the copolymer, is hydrophilic block, and can protect stability of nano particles in blood circulation; phenylalanine provides high pi-pi stacking effect and hydrophobic effect to stabilize assembling of the nano particles and to prevent the nano particles from disassembling in blood circulation; and glumatic acid unit provides effective drug carrying groups. The amino acid block copolymer is simple to prepare, good in biocompatibility, good in stability, easy to compound with a plurality of bioactive ingredients to achieve efficient drug carrying, and capable of controlled releasing the active pharmaceutical ingredients. The compound nano particles have wide application prospect in the bio-medical field, and particularly in the oncotherapy field.

Description

technical field [0001] The invention relates to the technical field of amino acids, in particular to amino acid block copolymers and their preparation methods and complexes. Background technique [0002] Polyamino acid polymers have similar structures and properties to natural polypeptides, and are a new class of polymer materials with good biocompatibility, biodegradability, and side group modifiability, and are widely used in biomedical fields, such as bioseparation , tissue engineering, gene therapy and drug controlled release, etc. [0003] L-glutamic acid polymer is a polyamino acid with a carboxyl group in the side chain. Due to the good reactivity of the side carboxyl group, it can carry various types of molecules or ionic compounds through electrostatic or covalent interactions, so it has a wide range of applications. field. L-phenylalanine polymer can improve the assembly stability of the polymer due to its strong π-π stacking interaction and hydrophobic interacti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/40A61K47/34A61K49/00A61K9/14A61K9/107
Inventor 汤朝晖吕世贤陈学思李明强宋万通于海洋
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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