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Amphiphilic multi-block antibacterial peptide copolymer, and preparation method and application thereof

A multi-block, antibacterial peptide technology, applied in the field of amphiphilic multi-block antibacterial peptide copolymer and its preparation, can solve the problems of high cost, complicated extraction process of natural antibacterial peptide, low yield and the like, and achieves low cost, Excellent broad-spectrum antibacterial properties, achieving the effect of mass production

Inactive Publication Date: 2019-12-03
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, it is of far-reaching research significance to synthesize antibacterial agents similar in structure to natural antimicrobial peptides by chemical synthesis.

Method used

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  • Amphiphilic multi-block antibacterial peptide copolymer, and preparation method and application thereof
  • Amphiphilic multi-block antibacterial peptide copolymer, and preparation method and application thereof
  • Amphiphilic multi-block antibacterial peptide copolymer, and preparation method and application thereof

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preparation example Construction

[0074]

[0075] The preparation method of amphiphilic multi-block class antimicrobial peptide copolymer comprises the steps:

[0076] (1), the synthesis of the hydrophilic amino acid block containing amino protecting group:

[0077] (1-1), react the hydrophilic amino acid containing the amino protecting group and triphosgene in an organic solvent to obtain the crude product of the hydrophilic amino acid-N-carboxyl-α-amino acid anhydride monomer containing the amino protecting group product, its structural formula is:

[0078]

[0079] Wherein, Z represents an amino protecting group;

[0080] (1-2) Dissolving the crude product of the hydrophilic amino acid-N-carboxy-α-amino acid anhydride monomer containing an amino protecting group in an organic solvent, and then performing recrystallization and purification in n-hexane. Repeat the steps of dissolving, precipitating and re-dissolving, and after rotary evaporation and drying, the pure product of hydrophilic amino acid-N-...

Embodiment 1

[0128] The amphiphilic triblock antimicrobial peptide copolymer K of the present embodiment 7 f 7 K 7 The preparation method comprises the steps:

[0129] (1) Add 10.0g (35.714mmol) of N(ε)-benzyloxycarbonyl-L-lysine into 50mL tetrahydrofuran, and 31.8g (107.142mmol) of triphosgene (take the amount of the above-mentioned lysine substance 3 times) within 30min dropwise into the THF solution of lysine, stirred and reacted for 8h under heating in an oil bath at 60°C, after the reaction was completed, the reaction solution was dropped dropwise into n-hexane, recrystallized and purified, and filtered Remove tetrahydrofuran to obtain the crude product of benzyloxycarbonyl (Z)-L-lysine-N-carboxyl-α-amino acid anhydride monomer; then filter the obtained benzyloxycarbonyl (Z)-L-lysine-N -Carboxyl-α-amino acid anhydride monomer was dissolved in tetrahydrofuran, and dropped dropwise into n-hexane, recrystallized for purification, and tetrahydrofuran was discarded by filtration. Repea...

Embodiment 2

[0146] The amphiphilic five-block antimicrobial peptide copolymer K of the present embodiment 5 f 5 K 5 f 5 K 5 The preparation method comprises the steps:

[0147] (1) Add 10.0g (35.714mmol) of N(ε)-benzyloxycarbonyl-L-lysine to 50mL of tetrahydrofuran, and 21.2g (71.428mmol) of triphosgene (taking the amount of the above-mentioned lysine substance) 2 times) within 30min dropwise into the tetrahydrofuran solution of lysine, stirred and reacted for 8h under heating in an oil bath at 60°C; after the reaction was completed, the reaction solution was dropped into n-hexane, recrystallized and purified, filtered and discarded Tetrahydrofuran to obtain the crude product of benzyloxycarbonyl (Z)-L-lysine-N-carboxyl-α-amino acid anhydride monomer; then filter the obtained benzyloxycarbonyl (Z)-L-lysine-N- The carboxyl-α-amino acid anhydride monomer is dissolved in tetrahydrofuran, and dropped into n-hexane drop by drop, recrystallized and purified, and the tetrahydrofuran is disc...

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Abstract

The invention provides anamphiphilic multi-block antibacterial peptide copolymer, and a preparation method and application thereof. According to the amphiphilic multi-block antibacterial peptide copolymer,a hydrophobic amino acid block and a hydrophilic amino acid block are selected and usedfor simulating and replacingan amino acid composition in natural antibacterial peptide, therefore, excellentbroad-spectrum antibacterial performance, low cytotoxicity, excellent biocompatibility and biodegradability are achieved, an antibacterial mechanism of the amphiphilic multi-block antibacterial peptide copolymer is the same as that of the natural antimicrobial peptide, bacteria die by destroying bacterial cell membranes, andthe bacteria is not prone to being inducedto produce drug resistance.According to synthesis steps of the preparedamphiphilic multi-block antimicrobial peptide copolymer is simpler, efficient and lower in production cost compared with step-by-step synthesis reaction, and the amphiphilic multi-block antibacterial peptide copolymer can be used as an antimicrobial agent or drug carriers to be used in aspects of clinical anti-infection, targeted release of anticancer drugsor nanomedicine.

Description

technical field [0001] The invention belongs to the technical field of biomedical polymer materials, and in particular relates to an amphiphilic multi-block antimicrobial peptide copolymer with good biocompatibility, a preparation method and application thereof. Background technique [0002] The abuse of antibiotics leads to the emergence of drug-resistant bacteria and superbugs, and it is urgent to find antibacterial agents that can replace antibiotics and have different antibacterial mechanisms than traditional antibiotics. Natural antimicrobial peptides have broad-spectrum and high-efficiency bactericidal activity, and their membrane destruction mechanism is different from traditional antibiotics, that is, positively charged hydrophilic amino acids are adsorbed to the surface of negatively charged bacterial cell membranes through electrostatic interaction, and then hydrophobic amino acid residues are inserted into the bacterial cell membranes In the process, holes are for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/14C08G69/00A61K47/34
CPCA61K47/34C08G69/00C08G69/14
Inventor 周春才
Owner TONGJI UNIV
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