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Antibacterial peptoid and vesicle and preparation method and application thereof

A technology of antimicrobial peptides and vesicles, which is applied in the field of antimicrobial peptides and vesicles and their preparation, which can solve the problems of restricting the large-scale application of antimicrobial peptides, difficult mass production, complex process flow, etc., and achieve low cost and low environmental pollution , The effect of simple preparation steps

Inactive Publication Date: 2017-01-04
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the antimicrobial peptides currently used are directly extracted from nature or synthesized by biological or chemical methods, but the above-mentioned methods are complicated in process flow, high in cost, and difficult to mass-produce, thus restricting the large-scale application of antimicrobial peptides

Method used

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  • Antibacterial peptoid and vesicle and preparation method and application thereof
  • Antibacterial peptoid and vesicle and preparation method and application thereof
  • Antibacterial peptoid and vesicle and preparation method and application thereof

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preparation example Construction

[0074]

[0075] The preparation method of class antibacterial peptide comprises the steps:

[0076] (1), ε-Z-lysine sodium with amino protecting group reacts with diisocyanate or diisocyanate derivatives in DMSO solvent and at room temperature, the amino group of ε-Z-lysine sodium reacts with diisocyanate or the isocyanate group (NCO) of the diisocyanate derivative is covalently connected, the resulting reaction solution is precipitated in an acidic environment, and the precipitate is taken to obtain a dicarboxylic acid monomer;

[0077] (2), dicarboxylic acid monomers and diisocyanates or diisocyanate derivatives undergo condensation reactions in DMSO solvents to obtain peptide-like copolymers; in this type of polypeptide copolymers, the carboxyl groups of dicarboxylic acid monomers and diisocyanate or Amino groups (derived from isocyanate groups) of diisocyanate derivatives are covalently linked, and diisocyanates or diisocyanate derivatives form diisocyanate units;

[00...

Embodiment 1

[0112] The preparation method of the antimicrobial peptides of the present embodiment comprises the following steps:

[0113] (1), attach benzyloxycarbonyl (as an amino protecting group) to ε‐Z‐lysine to obtain ε‐Z‐lysine with benzyloxycarbonyl;

[0114] (2), 20.000g (71.4mmol) of ε‐Z‐lysine with benzyloxycarbonyl and 2.857g (71.4mmol) of NaOH were neutralized in water at room temperature, stirred for 2 hours, and waited for complete reaction Finally, remove the water in the solution with rotary evaporation to obtain ε-Z-lysine sodium with benzyloxycarbonyl;

[0115] (3), 10g (313.4mmol) ε-Z-lysine sodium with benzyloxycarbonyl (i.e. amino protecting group) and 2.633g (156.7mmol) hexamethylene diisocyanate in 100mL of DMSO solvent React at room temperature for 4 hours. After the reaction is over, the reaction solution is obtained. Pour the reaction solution into 1L of water, slowly add 1mol / L hydrochloric acid solution dropwise while stirring, stop the dropwise addition of hy...

Embodiment 2

[0142] The preparation method of the antimicrobial peptides of the present embodiment comprises the following steps:

[0143] (1), attach benzyloxycarbonyl (as an amino protecting group) to ε‐Z‐lysine to obtain ε‐Z‐lysine with benzyloxycarbonyl;

[0144] (2), 20.000g (71.4mmol) of ε‐Z‐lysine with benzyloxycarbonyl and 2.857g (71.4mmol) of NaOH were neutralized in water at room temperature, stirred for 2 hours, and waited for complete reaction Finally, remove the water in the solution with rotary evaporation to obtain ε-Z-lysine sodium with benzyloxycarbonyl;

[0145] (3), 10g of ε‐Z‐lysine sodium with benzyloxycarbonyl (i.e. amino protecting group) and 2.508g of p-phenylene diisocyanate were reacted at room temperature in 100mL of DMSO solvent for 4h, and the reaction solution was obtained after the reaction , pour the reaction solution into 1L water, slowly add 1mol / L hydrochloric acid solution dropwise while stirring, stop adding hydrochloric acid solution dropwise until th...

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Abstract

The invention provides an antibacterial peptoid and a vesicle and a preparation method and application thereof. A hydrophilic part of the antibacterial peptoid is a lysine residue, and a hydrophobic part of the antibacterial peptoid is a diisocyanate unit, and the lysine residue links with the diisocyanate unit by means of a covalent bond. The antibacterial drug-loading vesicle is formed by self-assembling of the antibacterial peptoid and a drug in a mixture of an organic solvent and water. The antibacterial peptoid of the invention has a similar structure to that of a natural cationic anti-microbial peptide, and thus has a similar antibacterial mechanism; the antibacterial peptoid has broad-spectrum antibacterial properties, and cause the bacteria to be hard to produce drug resistance thereto; the antibacterial drug-loading vesicle has both antibacterial effect and dug-loading function, and can achieve sustained drug release.

Description

technical field [0001] The invention belongs to the field of polymer materials, and relates to antimicrobial peptides and vesicles, their preparation methods and applications. Background technique [0002] At present, antibiotics are mostly used for antibacterial at home and abroad. However, long-term use or abuse of antibiotics may lead to the emergence of drug-resistant bacteria, thereby rendering antibiotics ineffective. [0003] In order to avoid the adverse effects brought by the use of antibiotics, people sometimes use antimicrobial peptides instead of antibiotics for antibacterial. Antimicrobial peptide is a kind of polypeptide compound, which is adsorbed to the cell membrane of bacteria through electrostatic interaction, and its hydrophobic amino acid is inserted into the cell membrane to cause the rupture of the cell membrane, resulting in the death of bacteria. Therefore, its antibacterial mechanism is significantly different from that of antibiotics, so The use o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/83C08G18/38A61K9/127
CPCA61K9/127C08G18/3829C08G18/83
Inventor 周春才杜建忠袁跃
Owner TONGJI UNIV
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