Synthesis for biodegradable amphiphilic block copolymerization antibacterial peptoids, preparation method of antibacterial peptoid vesicles and applications of antibacterial peptoid vesicles

An amphiphilic block and antimicrobial peptide technology, which is applied in the direction of antibacterial drugs, drug combinations, peptide/protein components, etc., can solve the problems of high cost, complex extraction process of natural antimicrobial peptides, low yield, etc., and achieve low cost, Excellent broad-spectrum antibacterial performance, realizing the effect of industrial production

Inactive Publication Date: 2017-12-26
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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  • Synthesis for biodegradable amphiphilic block copolymerization antibacterial peptoids, preparation method of antibacterial peptoid vesicles and applications of antibacterial peptoid vesicles
  • Synthesis for biodegradable amphiphilic block copolymerization antibacterial peptoids, preparation method of antibacterial peptoid vesicles and applications of antibacterial peptoid vesicles
  • Synthesis for biodegradable amphiphilic block copolymerization antibacterial peptoids, preparation method of antibacterial peptoid vesicles and applications of antibacterial peptoid vesicles

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preparation example Construction

[0084] A method for preparing the above-mentioned biodegradable amphiphilic block copolymerized antimicrobial peptides, which comprises the steps of:

[0085] (1), the preparation of the hydrophilic polypeptide segment containing amino protecting group:

[0086] (1-1), react the hydrophilic amino acid containing amino protecting group and triphosgene in an organic solvent to obtain the hydrophilic amino acid-N-carboxyl-α-amino acid anhydride monomer containing amino protecting group, which The structural formula is:

[0087]

[0088] Among them, R 1 Represents the hydrophilic group of a hydrophilic amino acid, and Z' represents an amino protecting group;

[0089] (1-2), the hydrophilic amino acid-N-carboxyl-α-amino acid anhydride monomer containing an amino protecting group and the initiator of the polymerization of the hydrophilic amino acid are dissolved in an organic solvent and reacted under vacuum to obtain Hydrophilic polypeptide chain segment containing amino prot...

Embodiment 1

[0147] The synthesis of biodegradable amphiphilic block-copolymerized antimicrobial peptides and the preparation method of antimicrobial peptide vesicles in this embodiment include the following steps:

[0148] (1) Add 20.000g (71.428mmol) benzyloxycarbonyl‐lysine and 10.598g (35.714mmol) triphosgene to 200mL tetrahydrofuran, the reaction temperature is 50°C, and react for 5h to obtain benzyloxycarbonyl‐lysine‐ N-carboxy-α-amino acid anhydride monomer, its structural formula is:

[0149]

[0150] (2) Dissolve 30.475mg (0.417mmol) isobutylamine (as an initiator), 3.000g (9.804mmol) benzyloxycarbonyl-lysine-N-carboxyl-α-amino acid anhydride monomer in 20mL dimethylmethylene In sulfone, vacuum reaction at 25°C for 12h to obtain poly(benzyloxycarbonyl-lysine), its structural formula is:

[0151]

[0152] (3) Add 2.121g (13.158mmol) tert-butoxycarbonyl (Boc)-aminoethanol (as an initiator), 30.00g (263.16mmol) caprolactone to 100mL toluene, and add 2 drops of stannous octoate...

Embodiment 2

[0171] The synthesis of biodegradable amphiphilic block-copolymerized antimicrobial peptides and the preparation method of antimicrobial peptide vesicles in this embodiment include the following steps:

[0172] (1) Add 10.000g (35.714mmol) benzyloxycarbonyl-lysine and 5.299g (17.857mmol) triphosgene to 100mL tetrahydrofuran, the reaction temperature is 50°C, and react for 5h to obtain benzyloxycarbonyl-lysine- N-carboxy-α-amino acid anhydride monomer, its structural formula is:

[0173]

[0174] (2) Dissolve 92.348mg (1.263mmol) isobutylamine (as an initiator), 5.000g (16.340mmol) benzyloxycarbonyl-lysine-N-carboxy-α-amino acid anhydride monomer in 20mL dimethylmethylene In sulfone, vacuum reaction at 20°C for 12h to obtain poly(benzyloxycarbonyl-lysine), its structural formula is:

[0175]

[0176] (3) Add 2.121g (13.158mmol) tert-butoxycarbonyl (Boc)-aminoethanol (as an initiator), 30.00g (263.16mmol) caprolactone to 100mL toluene, and add 2 drops of stannous octoate (a...

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Abstract

The invention provides synthesis for biodegradable amphiphilic block copolymerization antibacterial peptoids, a preparation method of antibacterial peptoid vesicles and applications of the antibacterial peptoid vesicles. The synthesis for the antibacterial peptoids comprises the following steps: a hydrophilic polypeptide chain segment containing an amino protective group, a hydrophobic polymer chain segment of which one end is amino-terminated and isocyanate radicals of a diisocyanate unit are connected through covalent bonds, and therefore the antibacterial peptoids are obtained; and the antibacterial peptoid vesicles are formed by self assembly of the antibacterial peptoids, and the antibacterial peptoid vesicles can be used as antibacterial agents or drug carriers to be applied to aspects such as clinical inflammation resistance, anti-cancer drug targeting release, or nanomedicine. The antibacterial peptoid vesicles select and use the biodegradable hydrophobic polymer chain segment to replace a hydrophobic amino acid chain segment in an antibacterial peptide, thus the antibacterial peptoid vesicles do not have cytotoxicity, and have excellent biocompatibility and biodegradability; and besides, the antibacterial peptoid vesicles have a broad-spectrum antibacterial property, and a membrane damage antibacterial mechanism which is similar to that of a natural antibacterial peptide, and therefore drug tolerance of germs is not easily induced.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials, and in particular relates to the synthesis of biodegradable amphiphilic block copolymerized antimicrobial peptides and the preparation method and application of antimicrobial peptide vesicles. Background technique [0002] The abuse of antibiotics leads to the emergence of drug-resistant bacteria, and it is imminent to find antibacterial agents that are different from the antibacterial mechanism of traditional antibiotics. Natural antimicrobial peptides have broad-spectrum and high-efficiency bactericidal activity, and their membrane destruction mechanism is different from that of traditional antibiotics, that is, they are adsorbed to the surface of bacterial cell membranes through electrostatic interaction, and then hydrophobic amino acid residues are inserted into the bacterial cell membranes, resulting in holes in the cell membranes. This special antibacterial mechanism makes it dif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/42C08G18/60C08G63/08C08G63/685C08G69/10C08J3/07A61K38/02A61K9/127A61K47/59A61K47/42A61K47/34A61P31/04A61P29/00A61P35/00
CPCA61K9/1273A61K38/02A61K47/34A61K47/42C08G18/4277C08G18/603C08G63/08C08G63/6852C08G69/10C08J3/07C08J2387/00
Inventor 周春才周欣宇
Owner TONGJI UNIV
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