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Amphiphilic grafted copolymer containing antibacterial peptide, and preparation method and applications thereof

A technology of graft copolymer and antibacterial peptide, which is applied to the field of amphiphilic graft copolymer containing antibacterial peptide and its preparation, can solve the problems of high cost, low yield, complicated extraction process of natural antibacterial peptide and the like, and achieves low cost , controllable structure, excellent broad-spectrum antibacterial properties

Inactive Publication Date: 2019-10-15
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the extraction process of natural antimicrobial peptides is complicated, the yield is low and the cost is high. Therefore, the synthesis of antibacterial agents with similar structures to natural antimicrobial peptides by chemical synthesis has far-reaching research significance.

Method used

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  • Amphiphilic grafted copolymer containing antibacterial peptide, and preparation method and applications thereof
  • Amphiphilic grafted copolymer containing antibacterial peptide, and preparation method and applications thereof
  • Amphiphilic grafted copolymer containing antibacterial peptide, and preparation method and applications thereof

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preparation example Construction

[0045]

[0046] The preparation method of the amphiphilic graft copolymer containing antimicrobial peptide of the present invention comprises the steps:

[0047] (1), with methoxypolyethylene glycol (mPEG) as a macromolecular initiator, stannous isooctanoate as a catalyst, ε-caprolactone and functionalized ε-caprolactone monomer 6-(benzyl acetate ε-caprolactone / 6-(benzyl acetate)-ε-caprolactone containing pendant benzyl acetate group by ring-opening copolymerization of BCL in organic solvent Copolymer (PCL-co-PBCL), and the benzyl protecting group was removed under the condition of palladium carbon catalytic hydrogenation, and a series of poly(ε-caprolactone) (mPEG- b-P(2-CCL-co-6-CCL)), which is a hydrophobic polymer, denoted as G, its structural formula is:

[0048]

[0049] Wherein, J and K represent the degree of polymerization of the random copolymerization block in the hydrophobic macromolecule (G) respectively;

[0050] (2) React the hydrophobic polymer, N,N'-dic...

Embodiment 1

[0072] The preparation method of the amphiphilic graft copolymer G-EPL containing ε-polylysine of the present embodiment comprises the steps:

[0073] (1) Using methoxypolyethylene glycol (mPEG) as an initiator, under the catalysis of stannous isooctanoate, ε-caprolactone and 10 g of functionalized ε-caprolactone monomer 6-(benzyl acetate Ring-opening copolymerization of ester group-ε-caprolactone) (BCL) in tetrahydrofuran to form ε-caprolactone / 6-(benzyl acetate group)-ε-caprolactone copolymer with pendant benzyl acetate group (PCL-co-PBCL). Then, the benzyl protecting group of PCL-co-PBCL was removed by palladium / carbon catalytic hydrogenation, and finally poly(ε-caprolactone) (PCL-co-PCCL) containing pendant ethyl carboxyl functional groups was obtained, which was highly hydrophobic. Molecule, denoted as G, its structural formula is:

[0074]

[0075] Wherein, J and K represent the degree of polymerization of the random copolymerization block in the hydrophobic macromo...

Embodiment 2

[0085] The preparation method of the amphiphilic graft copolymer G-melittin containing melittin of the present embodiment comprises the steps:

[0086] (1) Using methoxypolyethylene glycol (mPEG) as an initiator, under the catalysis of stannous isooctanoate, ε-caprolactone and 10 g of functionalized ε-caprolactone monomer 6-(benzyl acetate Ring-opening copolymerization of ester group-ε-caprolactone) (BCL) in tetrahydrofuran to form ε-caprolactone / 6-(benzyl acetate group)-ε-caprolactone copolymer with pendant benzyl acetate group (PCL-co-PBCL). Then, the benzyl protecting group of PCL-co-PBCL was removed by palladium / carbon catalytic hydrogenation to obtain poly(ε-caprolactone) (PCL-co-PCCL) containing pendant ethyl carboxyl functional groups, which is a hydrophobic polymer. Denoted as G, its structural formula is:

[0087]

[0088] Wherein, J and K represent the degree of polymerization of the random copolymerization block in the hydrophobic macromolecule (G) respectively...

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Abstract

The invention provides an amphiphilic grafted copolymer containing an antibacterial peptide, and a preparation method and applications thereof. The amphiphilic grafted copolymer is prepared through connection of hydrophobic high molecular chain segments and the antibacterial peptide through covalent bonds, and is used in clinical infection prevention, anticancer medicine targeting release, or nanometer medical science as an antibacterial agent or a drug carrier. According to the preparation method, the hydrophobic high molecular chain segments excellent in biocompatibility are adopted to replace hydrophobic amino acid chain segments in the antibacterial peptide, so that no cytotoxicity is caused, and excellent biocompatibility and biodegradability are achieved; and in addition, the amphiphilic grafted copolymer possesses excellent wide spectrum antibacterial properties, and membrane destroy antibacterial mechanism similar to that of natural antibacterial peptides, so that generation ofbacterium drug resistance is not easily induced. The amphiphilic grafted copolymer containing an antibacterial peptide is controllable in structure, synthesis steps are simple and convenient, production cost is low, and industrialized production can be realized.

Description

technical field [0001] The invention belongs to the technical field of medical polymer materials, and in particular relates to an amphiphilic graft copolymer containing antimicrobial peptides and its preparation method and application. Background technique [0002] Since the discovery of penicillin, antibiotics can be said to have brought good news to mankind in terms of antibacterial treatment. However, in recent years, due to the abuse and misuse of antibiotics, drug-resistant bacteria and superbugs have emerged, so it is imminent to find excellent antibacterial agents that are different from the antibacterial mechanism of traditional antibiotics. Natural antimicrobial peptides are found in the immune system of organisms. They not only have broad-spectrum and high-efficiency bactericidal activity, but also the membrane destruction mechanism of antimicrobial peptides is different from traditional antibiotics, that is, positively charged antimicrobial peptides are adsorbed t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/08C08G63/78C08G63/91A61K47/42A61K47/34A61K47/60A61K31/785A61K38/17A61P31/04
CPCA61K31/785A61K38/17A61K47/34A61K47/42A61K47/60A61P31/04C08G63/08C08G63/78C08G63/912C08G81/00
Inventor 周春才
Owner TONGJI UNIV
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