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Antibacterial peptide containing dopamine adhesion group and preparation method and application thereof

A dopamine and antimicrobial peptide technology, applied in the field of preparation of antimicrobial peptides, can solve the problems of damaging the surface of materials, cumbersome steps, and restricting development

Active Publication Date: 2020-04-03
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Pathogenic microorganisms such as bacteria and fungi often cause lesions in body tissues, seriously threatening human physical and mental health. The development of medical antibacterial materials and products has received more and more attention. Antimicrobial peptides have broad-spectrum antibacterial activity and are not easy to produce drug resistance. However, it has a wide range of potential applications in the surface modification of biomedical devices, but the high cost of its traditional preparation method limits its development.
Recently, some scholars have found that the polypeptide polymer prepared by ring-opening of amino acid anhydride (NCA) also has antibacterial properties. By adjusting its composition and length, a broad-spectrum antibacterial polypeptide polymer can be obtained. However, using this polypeptide polymer as an antibacterial When coating, in order to have good adhesion between the antibacterial coating and the coated material, the surface of the material is modified by the traditional chemical grafting method, which requires the surface of the coated material to be functionalized , this step is cumbersome and damages the surface of the material

Method used

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  • Antibacterial peptide containing dopamine adhesion group and preparation method and application thereof
  • Antibacterial peptide containing dopamine adhesion group and preparation method and application thereof
  • Antibacterial peptide containing dopamine adhesion group and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0069]

[0070] A kind of preparation method of above-mentioned antimicrobial peptide containing dopamine adhesion group, it comprises the steps:

[0071] (1-1) Reacting a hydrophilic amino acid containing an amino protecting group and triphosgene in an organic solvent to obtain a hydrophilic amino acid-N-carboxy-α-amino acid anhydride monomer: Among them, R 1 Represents the hydrophilic group of a hydrophilic amino acid, and Z' represents an amino protecting group;

[0072] (1-2) Reaction of hydrophobic amino acid and triphosgene in an organic solvent to obtain hydrophobic amino acid-N-carboxy-α-amino acid anhydride monomer: Among them, R 2 represents the hydrophobic group of a hydrophobic amino acid;

[0073] (1-3) react the dopamine adhesion unit containing the phenolic hydroxyl protecting group and phosphorus pentachloride in an organic solvent to obtain the dopamine adhesion unit-N-carboxy-α-amino acid anhydride monomer: Wherein, R represents an alkane segment, an...

Embodiment 1

[0116] (Lys 15 -ran-Phe 10 -ran-L-DOPA 6 ) Preparation of random copolymerized antimicrobial peptides

[0117] The preparation method of the antibacterial peptide containing dopamine adhesion unit dihydroxyphenylalanine (L-DOPA) and lysine (Lys) and phenylalanine (Phe) segment random copolymerization described in this example, it Including the following steps:

[0118] (1-1) Add 10.00g (35.71mmol) of benzyloxycarbonyl-lysine (Z'-Lys) and 4.61g (15.53mmol) of triphosgene into 100mL of THF, and react at constant temperature for 3h at a temperature of 50°C. Obtain lysine-N-carboxy-α-amino acid anhydride (Z'-Lys-NCA) monomer (Z' is represent benzyloxycarbonyl protecting group), the structural formula is:

[0119]

[0120] (1-2) Add 10.00g (37.71mmol) of phenylalanine (Phe) and 4.86g (16.38mmol) of triphosgene into 100mL of THF, and react at constant temperature for 3 hours at a temperature of 50°C for 3 hours to obtain benzene Alanine-N-carboxy-α-amino acid anhydride (Ph...

Embodiment 2

[0134] (Lys 15 -ran-Phe 10 -b-L-DOPA 6 ) Preparation of block copolymerized antimicrobial peptides

[0135] Described in this embodiment (Lys 15 -ran-Phe 10 -b-L-DOPA 6 ) the preparation method of block copolymerized antibacterial peptide, it comprises the steps:

[0136] (1-1) Add 10.00g (35.71mmol) benzyloxycarbonyl-lysine (Z'-Lys) and 4.61g (15.53mmol) triphosgene into 100mL THF, and react at constant temperature for 3h at a reaction temperature of 50°C to obtain Z'-Lys-NCA monomer (Z' is represent benzyloxycarbonyl protecting group), the structural formula is:

[0137] (1-2) Add 10.00g (37.71mmol) of phenylalanine (Phe) and 4.86g (16.38mmol) of triphosgene into 100mL of THF, and react at constant temperature for 3 hours at a temperature of 50°C for 3 hours to obtain Phe -NCA monomer, the structural formula is:

[0138]

[0139] (1-3) Under the protection of argon, add 6.00g (30.43mmol) L-DOPA and 34ml (34mmol) NaOH to 100ml distilled water, then add dissolve...

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Abstract

The invention belongs to the field of antibacterial biological materials, and provides an antibacterial peptide with dopamine adhesion groups, a method for preparing the antibacterial peptide and application thereof. The antibacterial peptide with the dopamine adhesion groups is prepared from hydrophilic amino acid, hydrophobic amino acid, dopamine adhesion units, triphosgene, organic solvents, initiators, deprotection agents and precipitators. The antibacterial peptide, the method and the application have the advantages that the antibacterial peptide with the dopamine adhesion groups has broad spectra, is excellent in antibacterial property and surface adhesion property and can be coated on the surfaces of materials to be stably adhered on the surfaces of the materials even in humid environments; the method is simple, conditions are controllable, the antibacterial peptide is an economic and efficient antibacterial coating material, and the antibacterial peptide and the method have broad application prospects and high values.

Description

technical field [0001] The invention belongs to the field of antibacterial biomaterials, in particular to a preparation method and application of an antibacterial peptide containing a dopamine adhesion group. Background technique [0002] Pathogenic microorganisms such as bacteria and fungi often cause lesions in body tissues, seriously threatening human physical and mental health. The development of medical antibacterial materials and products has received more and more attention. Antimicrobial peptides have broad-spectrum antibacterial activity and are not easy to produce drug resistance. While it has a wide range of potential applications in the surface modification of biomedical devices, the high cost of its traditional preparation methods limits its development. Recently, some scholars have found that the polypeptide polymer prepared by ring-opening of amino acid anhydride (NCA) also has antibacterial properties. By adjusting its composition and length, a broad-spectrum...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/08C08G69/48C09D5/14C09D177/02
Inventor 周春才周欣宇
Owner TONGJI UNIV