A chiral peptide antibacterial polymer with dendrimers as side chains and preparation method thereof

A technology of dendrimer and polymer, applied in the field of chiral peptide antibacterial polymer and its preparation, can solve the problems of high hemolytic toxicity of red blood cells and high production cost

Active Publication Date: 2021-03-16
SICHUAN UNIV
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  • Abstract
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Problems solved by technology

[0003] Aiming at the above-mentioned problems existing in the prior art, the present invention provides a novel chiral peptide antibacterial polymer with dendrimers as side chains and a preparation method thereof, so as to solve the problem that the existing peptide antibacterial polymers use solid-phase polypeptide The production cost caused by the synthetic method is high, and the problem of high hemolytic toxicity to red blood cells

Method used

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  • A chiral peptide antibacterial polymer with dendrimers as side chains and preparation method thereof
  • A chiral peptide antibacterial polymer with dendrimers as side chains and preparation method thereof
  • A chiral peptide antibacterial polymer with dendrimers as side chains and preparation method thereof

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Embodiment 1

[0052] A preparation method of a chiral peptide antibacterial polymer with dendrimers as side chains, comprising the following steps:

[0053] Preparation of first and second generation lysine dendrimers

[0054] 1. Preparation of left-handed molecules

[0055] Boc-L-Lys(Boc)-OH((S)-2,6-di-tert-butoxycarbonylaminocaproic acid, 5mmol), H-L-Lys-OMe·2HCl(L-lysine methyl ester dihydrochloride salt, 12.5mmol), HOBt (1-hydroxybenzotriazole, 12.5mmol), EDC HCl (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, 12.5 mmol) was added to 30 mL of anhydrous dichloromethane, and the mixed solution was kept in an ice bath at 0° C. for 1 hour. DIPEA (diisopropylethylamine, 8 mL) was added dropwise to the reaction system while cooling in ice. Then the reaction system was raised to room temperature and reacted for 48 hours. After the reaction was completed, 70 mL of chloroform was added to the reaction system, and washed alternately with saturated sodium bicarbonate solution, dil...

experiment example

[0111] Experimental example Molecular dynamics simulation of the interaction between the peptide antibacterial polymer of the present invention and the bacterial membrane

[0112] GROMACS version 2019.3 software package was used for molecular dynamics, GROMOS 53A7 force field was used, SPC model was used for water molecules, double-layer phospholipid membrane with POPG:POPE=1:3 was used for bacterial membrane model, and AutomatedTopology Builder (ATB) server was used for polymer molecules mold. In the initial stage, the polymer molecules were placed at 4.5nm above the phospholipid bilayer. In the system equilibrium stage, the energy optimization was performed using the steepest descent method and the conjugate gradient method, followed by constant temperature ensemble (NVT) and constant pressure ensemble (NPT). ) equilibrium, the temperature coupling uses the v-rescale method, and the temperature gradually increases to 310K. Finally, a 100ns simulation of the antibacterial po...

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Abstract

The invention provides a chiral peptide antibacterial polymer taking dendrimer as side chains and a preparation method thereof. The preparation method comprises the following steps: (1) preparing second-generation lysine dendrimer; (2) preparing an alpha-amino acid intra-cyclic anhydride monomer; (3) carrying out ring-opening polymerization of monomers; and (4) carrying out PEG formation and de-protection of a polymer precursor. A traditional solid-phase polypeptide synthesis method is not used; the production cost is low, and the prepared peptide polymer molecule has a unique structure, an alpha-spiral main chain structure and a composite radiation spiral structure taking dendrimer as a side chain, and has the advantages of high-efficiency broad-spectrum sterilization effect, low cytotoxicity and low hemolytic property.

Description

technical field [0001] The invention belongs to the technical field of peptide antibacterial polymers, in particular to a chiral peptide antibacterial polymer with dendrimers as side chains and a preparation method thereof. Background technique [0002] Infectious diseases caused by microorganisms pose a great threat to global public health. However, with the widespread use of antibiotics, the emergence of bacterial drug resistance in clinical practice is becoming more and more serious. Peptide antibacterial polymers have attracted people's attention as a countermeasure that is not easy to produce drug resistance and has a broad-spectrum bactericidal effect. Most of the existing peptide antibacterial polymers imitate or modify natural antibacterial peptides in terms of structure and composition. This makes it mostly synthesized by solid-phase peptide synthesis, which is a linear single-chain amino acid in structure and composition. Defects such as high hemolytic toxicity....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/00
CPCC08G81/00
Inventor 吴尧张宇佳易强英康珂
Owner SICHUAN UNIV
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