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Preparation and application of modified peptide

A reaction and derivative technology, applied in the field of new modified peptides and their preparation, can solve the problems of limited effect of Gram-negative bacteria and limited antibacterial effect, and achieve the effect of promoting wound healing, single component, and wide spectrum of antibacterial action

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

AI Technical Summary

Problems solved by technology

However, the antibacterial effect of RWRWRW is limited, and it only has an inhibitory effect on Gram-positive bacteria, and its effect on Gram-negative bacteria is limited

Method used

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  • Preparation and application of modified peptide
  • Preparation and application of modified peptide
  • Preparation and application of modified peptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of single carboxyl phthalocyanine zinc-antimicrobial peptide covalent compound

[0037] 1. Dissolve β-monocarboxyl-substituted zinc phthalocyanine in N,N-dimethylformamide (DMF) solvent at a concentration of 5 – 15mmol / L, and add twice the molar equivalent of O-benzotriazole- Tetramethyluronium hexafluorophosphate (HBTU) and N,N-diisopropylethylamine (DIEA) with a total volume ratio of 0.5% were activated at room temperature for 0.5 h, and then 1.2 times the molar equivalent of loaded antibacterial Peptide Wang resin (Shanghai Gill Biochemical Co., Ltd., 653334), after shaking at room temperature for 24 h, washed with DMF to remove unreacted β-monocarboxyl substituted zinc phthalocyanine, and dried to obtain zinc phthalocyanine loaded on Wang resin- Antimicrobial peptide covalent compound solid.

[0038] 2. The resin cutting fluid (TFA: triisopropylsilane: water = 95 : 2.5 : 2.5) prepared according to the volume ratio of 10-15 mL / g solid, ...

Embodiment 2

[0040] Example 2: Antibacterial properties of modified peptides

[0041]The experimental strains were Gram-positive Staphylococcus aureus (S. aurues, ATCC 6358), Gram-negative Escherichia coli (E.coli, ATCC 8739) and methicillin-resistant Staphylococcus aureus (MRSA, ATCC 33591 ),Specific steps are as follows:

[0042] (1) Dissolve the zinc phthalocyanine-antimicrobial peptide covalent compound in DMSO as a stock solution (1mmol / L), and dilute the stock solution 2-fold with a PBS solution containing 1% Tween20 to different concentrations (0.1 – 100 µmol / L) L), and then added to a 96-well transparent plate, each concentration was added to three wells as a parallel group, and 20 μL was added to each well, and a group added with the same volume of PBS was set as a control group.

[0043] (2) The experimental group was divided into two groups, namely the light group and the no-light group, and the no-light group was protected from light throughout the experiment.

[0044] (3) Dr...

Embodiment 3

[0050] Example 3: Wound Healing Promotion Experiment of Modified Peptides

[0051] Gram-positive Staphylococcus aureus (S. aurues, ATCC 6358) was selected as the experimental strain, and 4-week-old Kunming mice were fed and treated according to the recommendations of the Animal Care and Use Committee (IACUC) until their body weight reached 25 ± 2 g. The general schematic diagram of the experiment is as Figure 4 As shown, the specific steps are as follows:

[0052] (1) Divide the mice into three groups: the two groups were treated with Staphylococcus aureus (S. aureus) and ZnPcG under dark and light conditions respectively. 3 K 5 (RW) 3 Treatment successively, among them, the light group uses ZnPcG 3 K 5 (RW) 3 After treatment with bacteria, light with a wavelength of 680 nm (12.0 J / cm 2 ) One-time irradiation. Another group was only treated with Staphylococcus aureus (S. aureus) without light, 6 mice per group. During the whole experiment, mice in all experimental gr...

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Abstract

The invention relates to a preparation method of a modified peptide. The preparation method comprises the following steps: covalently coupling a polypeptide with a photosensitizer through three glycines (GGG), wherein the conjugate has a relatively strong antibacterial effect (the antibacterial rate) of 50%, and can effectively kill most microorganisms including drug-resistant bacteria under illumination, and the sterilization rate reaches 99.999%. The conjugate has the effects of preventing infection and promoting healing on cut wounds of mice. The compound is simple in preparation method, relatively high in yield and convenient to store, can be used for preparing products such as antibacterial reagents and antibacterial drugs, and has a good application prospect in the fields of clinicaltreatment of local infection and wound dressing.

Description

technical field [0001] The invention belongs to the field of novel compounds, and in particular relates to a novel modified peptide and its preparation method and application. Background technique [0002] With the prevalence of multidrug-resistant bacteria, the development of new antibiotics is far behind the development of bacterial resistance, so people urgently need a treatment that can replace antibiotics. Antimicrobial peptides are peptide substances with antibacterial effect secreted by organisms. They can effectively inhibit bacteria but are not easy to cause bacterial resistance mutations, so they have attracted people's attention. RWRWRW is a synthetic cationic hexapeptide, which can target and accumulate in the cell membrane of Gram-positive pathogenic bacteria, delocalize membrane proteins involved in cell wall synthesis and cellular respiration, and eventually lead to the death of pathogens. The selectivity of this antimicrobial peptide to pathogenic bacteria i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/08C07K1/20C07K1/107C07K1/08C07K1/04A61K38/10A61P31/04A61P17/02
CPCC07K7/08A61P31/04A61P17/02A61K38/00Y02A50/30
Inventor 黄明东张迪袁彩江龙光
Owner FUZHOU UNIV
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