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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: 2014-08-27
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 present invention also provides a kind of preparation method of polyamino acid graft copolymer, comprising:

[0060] react polyamino acid, hydrophilic compound and hydrophobic compound under the action of condensation accelerator to obtain 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 shown in formulas (5) to (8);

[0063] The hydrophobic compound is a hydroxyl-containing polyester, a C8-C30 fatty alcohol, or a biologically active small biomolecule;

[0064]

[0065]

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

[0067] R 1 is a group shown in formula (1) to formula (4);

[0068] R 2 It is a group other than a hydroxyl group of a polyester containing a hydroxyl group, a C8~C30 alkyl group, an aryl group, a C8~C30 alkenyl group, a C8~C30 alk...

Embodiment 1~3

[0081] Add 2.63g (0.01mol) of γ-benzyl-L-glutamate-N-internal carboxylic acid anhydride monomer and 30mL of anhydrous N,N-dimethylformamide into the reaction flask respectively, and stir to dissolve. 0.0002 mol, 0.0001 mol and 0.00005 mol of n-hexylamine were added under stirring conditions, and the reaction was continued for 72 hours under stirring at 25°C. After the reaction, the reaction mixture was settled with 300 mL ether, filtered, washed three times with ether, and vacuum-dried 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 with deuterated trifluoroacetic acid as a solvent, and its 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 Number-average molecular weight, average degree of polymerization and ...

Embodiment 4~6

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

[0092] Dissolve 1 g of the above-mentioned poly(γ-benzyl-L-aspartic acid ester) in 10 mL of dichloroacetic acid, and add 3 mL of hydrogen bromide / glacial acetic acid solution with a mass content of 33% under stirring conditions to obtain a reaction mixture After the reaction mixture was stirred at 25°C for 1 h, the obtaine...

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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 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 macromolecules have good side group modification, biodegradability, biocompatibility and regular secondary structure. Wide application prospects. However, due to the limited functionality of a single polyamino acid, its application is also limited. [0003] It is one of the important ways to improve the properties of polyamino acid polymer materials by introducing the second component into polyamino acid polymer materials to prepare copolymers. By adjusting the type of copolymer monomer, the proportion of each component and the molecular weight of the obtained copolymer to control the performance of the copolymer, and to endow the copolymer with new characteristics for each component material, it can greatly expand the application field of polyamino acid materials . ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/34C08G81/00C08G69/48
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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