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Symmetric short-sequence antimicrobial peptide analogues and application thereof

An antibacterial peptide and analog technology, applied in the field of biochemistry, can solve the problems of long sequence, high manufacturing cost, complex design, etc., and achieve the effects of low drug resistance, low manufacturing cost, and simple design

Active Publication Date: 2020-07-03
倪京满 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above studies on antimicrobial peptide analogs have achieved remarkable results, there are still problems of high manufacturing costs due to long sequences and complex designs.

Method used

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  • Symmetric short-sequence antimicrobial peptide analogues and application thereof
  • Symmetric short-sequence antimicrobial peptide analogues and application thereof
  • Symmetric short-sequence antimicrobial peptide analogues and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of WRW and its in vitro antibacterial activity and hemolytic toxicity research

[0048] (1) Synthesis of WRW

[0049] ①Activation and pretreatment of resin

[0050] Accurately weigh 0.69g of MBHA resin (substitution value 0.44mmol / g) and place it in a synthesizer. After swelling with DCM solution for 30min, the ninhydrin colorimetry test shows that the resin is colorless and transparent, indicating that the resin is normal.

[0051] ② Synthesis of WRW-resin

[0052] The normal MBHA resin of the above-mentioned inspection was sloughed off the Fmoc protecting group through the DMF solution containing 20% ​​piperidine by volume fraction, and the ninhydrin chromogenic method was tested, and the resin was blue-purple, indicating that the Fmoc protecting group had been removed; the Fmoc-Trp ( Boc)-OH (390mg), HOBT (123mg), HBTU (342mg), and DIEA (0.3ml) were dissolved in 8ml DMF and mixed evenly, and mixed with the above-mentioned MBHA resin whose Fmoc ...

Embodiment 2

[0063] Example 2: Synthesis of GWRW and its in vitro antibacterial activity and hemolytic toxicity research

[0064] (1) Synthesis of GWRW

[0065] ①Activation and pretreatment of resin

[0066] With embodiment 1.

[0067] ② Synthesis of GWRW-resin

[0068] For the above-mentioned normal MBHA resin, the Fmoc protecting group was removed by the DMF solution containing 20% ​​piperidine by volume fraction, and the ninhydrin chromogenic method was used to detect that the resin was blue-purple, indicating that the Fmoc protecting group had been removed; the Fmoc-Gly- OH (267mg), HOBT (123mg), HBTU (342mg), and DIEA (0.3ml) were dissolved in 8ml DMF and mixed evenly, and mixed with the above-mentioned MBHA resin whose Fmoc protecting group was removed, and condensed for 1 hour; ninhydrin developed color If the resin is colorless and transparent, it indicates that the condensation reaction is successful and Fmoc-Gly-resin is obtained; the method is the same as above, and the follo...

Embodiment 3

[0079] Example 3: Synthesis of IWRW and its in vitro antibacterial activity and hemolytic toxicity research

[0080] (1) Synthesis of IWRW

[0081] ①Activation and pretreatment of resin

[0082] With embodiment 1.

[0083] ②Synthesis of IWRW-resin

[0084] The normal MBHA resin of the above-mentioned inspection was removed the Fmoc protecting group through the DMF solution containing 20% ​​piperidine by volume fraction, and the ninhydrin chromogenic method was tested, and the resin was blue-purple, indicating that the Fmoc protecting group had been removed; the Fmoc-Ile- OH (399mg), HOBT (123mg), HBTU (342mg), DIEA (0.3ml) were dissolved in 8ml DMF and mixed evenly, and mixed with the above-mentioned MBHA resin from which the Fmoc protecting group was removed, and the condensation reaction was carried out for 1 hour; ninhydrin developed color Method test, the resin is colorless and transparent, it shows that the condensation reaction is successful, and Fmoc-Ile-resin is obtai...

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Abstract

The invention designs and synthesizes a class of symmetric short-sequence antibacterial peptide analogues. The symmetric short-sequence antibacterial peptide analogues are obtained by taking tryptophan ''WWW'' as a mirror symmetry center by introducing arginine and hydrophobic amino acid of positive charges to two sides respectively, and then, carrying out C terminal amidation, and structural formulas of the symmetric short-sequence antibacterial peptide analogues are XYWWWYX-NH 2, XWYWWWYWX-NH 2 and XYYWWWYYX-NH2 respectively, wherein X is equal to G, I, L, F, W, V, A, and Y is equal to R. The antibacterial peptide analogues are simple in structural design, and low in manufacturing cost. In vitro bacteriostasis experiments, hemolysis experiments and induced resistance experiments show that the symmetric short-sequence antimicrobial peptide analogues have high antibacterial activity on strains of common gram-positive bacteria and gram negative bacteria, and have low hemolytic toxicity,cannot easily induce bacteria to produce drug resistance, and have good application prospects in the preparation of clinical antibacterial drugs.

Description

technical field [0001] The invention belongs to the technical field of biochemistry and relates to a class of symmetrical short-sequence antimicrobial peptide analogues. The invention also relates to the application of the antimicrobial peptide analogues in the preparation of clinical antibacterial drugs. Background technique [0002] The abuse and overuse of antibiotics, as well as the failure to discover new small molecule antibiotics in time, have led to the outbreak of the antibiotic crisis, and the emergence of "super bacteria" that are resistant to almost all available antibiotics (Lancet InfectDis.2013Dec; 13(12 ):1057-98). Currently, about 700,000 people worldwide die each year from antibiotic resistance. This phenomenon is expected to intensify in the next few years, and antibiotic resistance will become the leading cause of death worldwide, with an estimated 10 million deaths per year due to antibiotic resistance by 2050. [0003] Antimicrobial peptides (AMPs, An...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06A61K38/08A61P31/04
CPCC07K7/06A61P31/04A61K38/00Y02A50/30
Inventor 倪京满王锐钟超王一杰
Owner 倪京满
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