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Fatty-acid-modified ultra-short sequence antibacterial peptide analogue and application thereof

A fatty acid and antimicrobial peptide technology, applied in the field of biochemistry, can solve the problems of high manufacturing cost and complex design, and achieve the effect of low manufacturing cost, simple design and enhanced antibacterial activity

Pending Publication Date: 2020-03-31
倪京满
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention patent with application number 201410616342.6 (a small molecule synthetic antimicrobial peptide and its preparation method and application) discloses a sequence of RWWRF-NH 2 (Arg-Arg-Trp-Trp-Arg-NH 2 ) small molecule antimicrobial peptide, which has broad-spectrum antibacterial activity against Gram-negative and positive bacteria, but this antimicrobial peptide is based on the existing antimicrobial peptide Lactoferricin B 4-9 Based on the sequence, combined with the virtual new combination library design technology, using DNAstar, Bioedit, sequence logo and other analysis software and websites, the series of pentapeptide molecules obtained after amino acid substitution and interception still have high manufacturing costs due to complex design. question

Method used

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  • Fatty-acid-modified ultra-short sequence antibacterial peptide analogue and application thereof
  • Fatty-acid-modified ultra-short sequence antibacterial peptide analogue and application thereof
  • Fatty-acid-modified ultra-short sequence antibacterial peptide analogue and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: C 8 Synthesis of -R1 and its antibacterial activity in vitro

[0043] (1)C 8 -Synthesis of R1

[0044] ①Activation and pretreatment of resin

[0045] Accurately weigh 0.58g 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.

[0046] ② Synthesis of Fmoc-R1-resin

[0047] 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 (103mg), HBTU (285mg), and DIEA (0.25mL) were dissolved in about 10mL DMF and mixed evenly, added to the synthesizer and mixed with the above-mentioned MBHA res...

Embodiment 2

[0057] Example 2: C 12 Synthesis of -R1 and its antibacterial activity in vitro

[0058] (1)C 12 -Synthesis of R1

[0059] ①Activation and pretreatment of resin

[0060] With embodiment 1.

[0061] ② Synthesis of Fmoc-R1-resin

[0062] With embodiment 1.

[0063] ③C 12 -Synthesis of R1-resin

[0064] The Fmoc-R1-resin obtained above was also removed with the DMF solution containing 20% ​​piperidine to remove the terminal Fmoc protecting group, and dodecanoic acid (300mg), HOBT (103mg), HBTU (285mg), DIEA (0.25mL ) was dissolved in about 10mL DMF and mixed evenly, and mixed with the above-mentioned R1-resin resin from which the Fmoc protecting group was removed, and the condensation reaction was carried out for 1.5h; the ninhydrin color method was used to test that the resin was colorless, indicating that the condensation reaction was complete, and C was obtained. 12 -R1-resin.

[0065] ④ Peptide cleavage

[0066] With embodiment 1.

[0067] ⑤ Peptide purification

...

Embodiment 3

[0072] Example 3: C 16 Synthesis of -R1 and its antibacterial activity in vitro

[0073] (1)C 16 -Synthesis of R1

[0074] ①Activation and pretreatment of resin

[0075] With embodiment 1.

[0076] ② Synthesis of Fmoc-R1-resin

[0077] With embodiment 1.

[0078] ③C 16 -Synthesis of R1-resin

[0079] The Fmoc-R1-resin obtained above was also removed with the DMF solution containing 20% ​​piperidine to remove the terminal Fmoc protecting group, hexadecanoic acid (384mg), HOBT (103mg), HBTU (285mg), DIEA (0.25mL ) was dissolved in about 10mL DMF and mixed evenly, and mixed with the above-mentioned R1-resin resin from which the Fmoc protecting group was removed, and the condensation reaction was carried out for 1.5h; the ninhydrin color method was used to test that the resin was colorless, indicating that the condensation reaction was complete, and C was obtained. 16 -R1-resin.

[0080] ④ Peptide cleavage

[0081] With embodiment 1.

[0082] ⑤ Peptide purification

[...

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Abstract

The invention designs and synthesizes a fatty-acid-modified ultra-short-sequence antibacterial peptide analogue. The antibacterial peptide analogue is fatty-acid-modified polypeptide containing threeamino acids; arginine and tryptophan are arranged and combined in different modes to obtain an ultra-short sequence polypeptide containing three amino acids; amidation is performed on the C tail end of the ultra-short-sequence polypeptide and an N tail end of the ultra-short sequence polypeptide is modified with a C8-C18 fatty acid chain. The sequence is shorter, the design is simple, and the manufacturing cost is low. The in-vitro antibacterial experiments show that the ultra-short-sequence antibacterial peptide analogue has strong antibacterial activity on common strains, the antibacterial activity on gram-positive bacteria is superior to that on gram-negative bacteria. The ultra-short-sequence antibacterial peptide analogue has the broad application prospects in preparation of clinicalantibacterial drugs.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and relates to a class of fatty acid modified ultrashort sequence antibacterial peptide analogs, and also relates to the application of the antibacterial peptide analogs in the preparation of clinical antibacterial drugs. Background technique [0002] The emergence of antibiotic-resistant bacteria, or "superbugs," has become a major health concern worldwide. According to a 2013 report by the World Centers for Disease Control and Prevention, approximately 23,488 people die from drug-resistant bacterial infections each year (Centers for Disease Control and Prevention, Antibiotic / Antimicrobial Resistance (AR / AMR) (2018)). Therefore, the research and development of new antibacterial drugs is imminent. Studies have found that the causes of bacterial drug resistance mainly include: changes in the permeability of bacterial cell membranes, degradation of antibacterial drugs by bacterial proteases, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/097C07K5/09A61K38/06A61P31/04
CPCC07K5/0817C07K5/0821A61P31/04A61K38/00
Inventor 倪京满王锐钟超王一杰
Owner 倪京满
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