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Pseudomonas aeruginosa resistant Magainin peptide modifier and preparation method thereof

A Pseudomonas aeruginosa and modification technology, applied in the field of biochemistry, can solve the problem of not having the ability to target and eliminate bacteria in cells, and achieve excellent antibacterial effect and improved antibacterial performance

Inactive Publication Date: 2015-06-17
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent application number: 200810157206.X, 200110085397.4 The melittin-maggain peptide hybrids synthesized by genetic engineering methods also do not have the ability to target and eliminate intracellular bacteria

Method used

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  • Pseudomonas aeruginosa resistant Magainin peptide modifier and preparation method thereof
  • Pseudomonas aeruginosa resistant Magainin peptide modifier and preparation method thereof
  • Pseudomonas aeruginosa resistant Magainin peptide modifier and preparation method thereof

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Effect test

Embodiment 1

[0072] The preparation method of the Magainin peptide modification M-MGN-I having antibacterial properties against Pseudomonas aeruginosa provided by the present invention: comprises the following steps:

[0073] In step 1, 2-CTC resin (1.4mmol / g, 178.6mg), tert-butyl (tBu) protected Fmoc serine (Fmoc-Ser(tBU)-OH) (287.6mg, 0.75mmol) and DIPEA (170μL, 2mmol ), HBTU (284.4mg, 0.75mmol) was placed in a reaction flask, DMF (15mL) was added to dissolve, and stirred for 6-12 hours. After the reaction is completed, let it stand still, drain the DMF, wash the resin with DMF, and obtain a yellow resin.

[0074] Step 2 Put the resin coupled with tert-butyl (tBu)-protected serine in step 1 into a microwave peptide synthesizer to run the peptide synthesis program: add hexahydropiperidine-DMF (1 / 4; 10mL) microwave (35W) Irradiate for 75s to remove the Fmoc protecting group, add DMF (15mL) to wash the resin, add tert-butoxycarbonyl (Boc) protected Fmoc lysine (Fmoc-Lys(Boc)-OH) (0.2mmol / m...

Embodiment 2

[0078] The preparation method of the Magainin peptide modification M-MGN-II having antibacterial properties against Pseudomonas aeruginosa provided by the present invention: comprises the following steps:

[0079] In step 1, 2-CTC resin (1.4mmol / g, 178.6mg), tert-butyl (tBu) protected Fmoc serine (Fmoc-Ser(tBU)-OH) (287.6mg, 0.75mmol) and DIPEA (170μL, 2mmol ), HBTU (284.4mg, 0.75mmol) was placed in a reaction flask, DMF (15mL) was added to dissolve, and stirred for 6-12 hours. After the reaction is completed, let it stand still, drain the DMF, wash the resin with DMF, and obtain a yellow resin.

[0080] Step 2 Put the resin coupled with serine with a protective group on the side chain in step 1 into a microwave peptide synthesizer to run the standard procedure of peptide synthesis: add hexahydropiperidine-DMF (1 / 4; 10mL) microwave (35W) Irradiate for 75s to remove the Fmoc protecting group, add DMF (15mL) to wash the resin, add trityl (Trt) protected Fmoc asparagine (Fmoc-As...

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Abstract

The invention provides a pseudomonas aeruginosa resistant Magainin peptide modifier and a preparation method thereof. The Magainin peptide can be natural peptide Magainin I or Magainin II; and according to a sequence from C-terminal to N-terminal, the glycine in the 23rd position of the Magainin peptide is connected to 6-(4-morpholine-1,8-naphthalimide)-lysine of the sequence K(nph)KK2(beta-Ala-NH2)4, namely M-MGN-I or M-MGN-II. The provided two novel Magainin peptide modifiers (M-MGN-I and M-MGN-II) both have an excellent broad-spectrum antibacterial effect, especially have an good antibacterial effect on infected cells or pseudomonas aeruginosa in living organisms, and are capable of removing pseudomonas aeruginosa in A549 cells and HBE cells specifically.

Description

technical field [0001] The invention belongs to the field of biochemistry, and specifically relates to a Magainin peptide modification having excellent antibacterial properties against Pseudomonas aeruginosa and a preparation method thereof. Background technique [0002] Antimicrobial peptides (Antimicrobial Peptides) are small molecule polypeptides with biological activity induced in organisms, with a molecular weight of about 2000-7000 and composed of 20-60 amino acid residues. Most of these active peptides have the characteristics of strong alkalinity, thermal stability and broad-spectrum antibacterial properties. Antimicrobial peptides kill bacteria by disrupting the integrity of the membrane, causing the loss of the intracellular barrier. Antimicrobial peptides are considered to have broad application prospects in the pharmaceutical industry because of their high antibacterial activity, wide antibacterial spectrum, many types, wide range of options, and the lack of res...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/46C07K1/06
CPCY02P20/55C07K14/463
Inventor 吴君臣董理朱玉姚德帆田禾
Owner EAST CHINA UNIV OF SCI & TECH
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