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Polyamino acid grafted copolymer and preparation method thereof

A graft copolymer and polyamino acid technology, applied in the field of polyamino acids, can solve the problems of deposition, lack of stabilizer protection, etc., and achieve the effects of not easy deposition, good biocompatibility and degradability, and easy drug carrying.

Active Publication Date: 2013-01-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the polyamino acid copolymer reported above has a large amount of charges under physiological conditions, and lacks the protection of stabilizers, which is easy to cause deposition under physiological conditions, thus limiting its application in vivo, especially in intravenous drug delivery.

Method used

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  • Polyamino acid grafted copolymer and preparation method thereof
  • Polyamino acid grafted copolymer and preparation method thereof
  • Polyamino acid grafted copolymer and preparation method thereof

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preparation example Construction

[0059] The invention also provides a preparation method of the polyamino acid graft copolymer, which includes:

[0060] The polyamino acid, the hydrophilic compound, and the hydrophobic compound are reacted under the action of a condensation promoter to obtain the polyamino acid graft copolymer as shown in formula (I);

[0061] The polyamino acid is polyglutamic acid, polyaspartic acid or polyglutamic acid-polyaspartic acid copolymer;

[0062] The hydrophilic compound is any one of the compounds represented by formulas (5) to (8);

[0063] The hydrophobic compound is a polyester containing a hydroxyl group, a C8-C30 fatty alcohol or a small biological molecule with biological activity;

[0064]

[0065]

[0066] Wherein, L is independently selected from methylene or ethylene;

[0067] R 1 Is a group represented by formula (1) to formula (4);

[0068] R 2 It is a hydroxyl-containing polyester group other than one hydroxyl group, C8~C30 alkyl, aryl, C8~C30 alkene group, C8~C30 alkynyl group...

Embodiment 1~3

[0081] Add 2.63 g (0.01 mol) of γ-benzyl-L-glutamate-N-lactam acid anhydride monomer and 30 mL of anhydrous N,N-dimethylformamide into the reaction flask, and stir to dissolve. Add 0.0002mol, 0.0001mol and 0.00005mol n-hexylamine under stirring conditions, and continue the reaction for 72h under stirring at 25°C. After the reaction, the reaction mixture was settled with 300 mL of ether, filtered, and then washed three times with ether, and dried under vacuum at room temperature for 24 hours to obtain intermediate products, namely poly(γ-benzyl-L-glutamate).

[0082] The poly(γ-benzyl-L-glutamate) was analyzed by nuclear magnetic resonance using deuterated trifluoroacetic acid as the solvent, and the number average molecular weight and average degree of polymerization were calculated according to the nuclear magnetic resonance spectrum. For the results, see Table 1.

[0083] Table 1 The number average molecular weight, average degree of polymerization and yield of the intermediate ...

Embodiment 4~6

[0091] Add 2.49g (0.01mol) of γ-benzyl-L-aspartate-N-lactam acid anhydride monomer and 30mL of anhydrous N,N-dimethylformamide into 3 reaction flasks, Stir to dissolve. Under stirring conditions, 0.0002mol, 0.0001mol and 0.00005mol n-hexylamine were added to the three reaction flasks respectively, and the reaction was continued for 72h under stirring at 25°C. After the reaction, the reaction mixture was settled with 300 mL of ether, filtered, washed with ether three times, and dried under vacuum at room temperature for 24 hours to obtain intermediate products, namely, poly(γ-benzyl-L-aspartate).

[0092] Dissolve 1g of the above-mentioned poly(γ-benzyl-L-aspartate) with 10mL of dichloroacetic acid, and add 3mL of hydrogen bromide / glacial acetic acid solution with a mass content of 33% under stirring to obtain a reaction mixture After stirring the reaction mixture at 25° C. for 1 h, the product obtained was settled with 150 mL of ether, filtered, dialyzed with water once, and lyo...

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Abstract

The invention provides a polyamino acid grafted copolymer shown as a formula (I). a preparation method of the polyamino acid grafted copolymer comprises the following step of: reacting polyamino acid, hydrophilic compound and hydrophobic compound under the action of a condensation accelerator, so as to obtain the polyamino acid grafted copolymer shown as the formula (I), wherein the polyamino acid is a copolymer of polyglutamic acid, polyaspartic acid or polyglutamic acid-polyaspartic acid; the hydrophilic compound is any one of compounds shown as formulas (5)-(8); and the hydrophobic compound is polyester containing hydroxyl, C8-C30 fatty alcohol or biological micromolecule with biological activity. The polyamino acid grafted copolymer prepared by the invention is stable in water-based medium, is difficult to deposit, can stably wrap drug and is applicable to vein transmission of the drug; and meanwhile, a main chain and a side chain of the polyamino acid grafted polymer are natural or synthetic molecules with good biocompatibility, so that the polyamino acid grafted copolymer has good biocompatibility and degradability.

Description

Technical field [0001] The present invention relates to the field of polyamino acid, in particular to a polyamino acid graft copolymer and a preparation method thereof. Background technique [0002] Polyamino acid polymers have good side group modification, biodegradability, biocompatibility and regular secondary structure. They are used in biomedical fields, such as bioseparation, tissue engineering, gene therapy, and controlled drug release. Wide application prospects. However, due to the limited functionality of a single polyamino acid, its application is also limited. [0003] The preparation of copolymers by introducing the second component into polyamino acid polymer materials is one of the important ways to improve the performance of polyamino acid polymer materials. By adjusting the types of copolymer monomers, the ratio of each component and the molecular weight of the obtained copolymer, the performance of the copolymer is controlled, and the new characteristics of each...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G69/48A61K47/34
Inventor 汤朝晖宋万通李明强丁建勋于海洋陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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