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Antimicrobial peptide with drug-resistance bacteria resistance activity and synthesis and application thereof
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An antibacterial peptide and drug-resistant bacteria technology, applied in the field of biochemistry, can solve the problems of natural antibacterial peptides are not very active and have a narrow antibacterial spectrum.
Active Publication Date: 2013-08-21
LANZHOU UNIVERSITY
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However, not all natural antimicrobial peptides have disadvantages, some natural antimicrobial peptides are not very active, and the antibacterial spectrum is relatively narrow, etc.
In addition, the mechanism of action of antimicrobial peptides is different from traditional antibiotics, and generally does not produce drug resistance, but there are always certain pathogenic microorganisms in nature, which are naturally resistant to drugs due to their very stable cellmembrane structure or functional characteristics sex
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Embodiment 1
[0072] Embodiment 1: the synthesis of antimicrobial peptide J-AM
[0073] (1) Activation and pretreatment of resin
[0074] Accurately weigh 0.7g of MBHA resin (0.43mmol / g), add it to the peptide solid-phase synthesizer, add DCM along the tube wall until the resin is completely immersed, stir for 30 minutes to fully swell the resin, and then remove the stirrer, DCM was aspirated (30 min).
[0075] (2) Synthesis of AC-pra-Anoplin-MBHA
[0076] a. Leu coupling: Wash the pretreated resin three times with DMF, each time for 3 min (2 min×3 times), use a vacuum pump to dry the solvent in the reactor, add 20% volume fraction of hexahydropyridine / DMF solution, stirred (2 min×4), and drained. After the reaction was completed, wash with DMF 3-4 times, 2 min each time. Test whether the Fmoc protecting group has been removed by ninhydrinchromogenic method: if it is colorless, the Fmoc protecting group has not been removed, repeat the above steps; if it is blue, the Fmoc protecting gr...
Embodiment 2
[0117] Embodiment 2: the synthesis of antimicrobial peptide analogue J-AA
[0118] (1) Activation and pretreatment of resin
[0119] With embodiment 1.
[0120] (2) Synthesis of AC-pra-Anoplin-MBHA
[0121] With embodiment 1.
[0122] (3) AC-Nle(N 3 Synthesis of )-Anoplin-MBHA
[0123] a. Coupling of Leu: wash the pretreated resin with DMF 3 times, each time for 2 minutes, after draining, add a mixed solution of DMF containing 20% hexahydropyridine, stir to make it fully react 4 times, each time After the reaction is completed, wash 3 times with DMF, each time for 2 minutes, the indene should be colored, and the resin that has been removed from Fmoc protection is obtained; dissolve 319 mg of Fmoc-protected Leu in DMF, stir to make it fully dissolved, and add HOBT 121.9mg and HBTU 344.2mg, stir to dissolve, then add 300ul DIEA, then mix with the resin deprotected by Fmoc, argon protection, stirring reaction at room temperature for 1h, indene detection colorless, drained,...
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Abstract
The invention designs antimicrobialpeptide with drug-resistance bacteria resistance activity and a novel structure. The antimicrobialpeptide is obtained by modifying amino acid at N tail ends of natural antimicrobialpeptide Anoplin and MPI respectively, then performing acetylization on the amino acid, and performing intermolecular connection on every two side chains of the peptide by replacing a -1H-1,2,3-triazole structure by one 1,4- under the 1,3-dipolar cycloaddition reaction of the click chemistry. The antimicrobial experiments and pyridiniumiodidedyeing method experiments for staphylococcus aureus and escherichia coli of the conventional gram-positive bacterium and clinically separated drug-resistant staphylococcus aureus and drug-resistant escherichia coli show that the J-AM peptide and the J-AA peptide which are synthesized by the method are higher in antimicrobial activity, higher in drug-resistance bacteria resistance activity and higher in cytomembrane film penetration capacity and has an obvious drug-resistance advantage of avoiding a drug-resistance phenomenon caused by the general antibiotics; and therefore, the antimicrobial peptide has an extremely high application prospect in preparation of clinical treatment medicines.
Description
technical field [0001] The invention belongs to the technical field of biochemistry, and relates to a novel structure antibacterial peptide with anti-drug-resistant bacteria activity; the invention also relates to a synthesis method of the antibacterial peptide and an application in preparing antibacterial drugs. Background technique [0002] With the extensive use of antibiotics in people's lives, drug-resistant strains continue to emerge, making many highly effective antibiotics ineffective, so seeking new antibiotics is becoming more and more important to human development. Antimicrobial Peptides (AMPs) refer to a class of small molecule polypeptides that are often positively charged, have broad-spectrum antibacterial properties, and have 12 to 50 amino acids. With the rapid development of molecular biology, the study of antimicrobial peptides has increasingly become a hot topic in the field of biomedicine (Hancock RE. Peptide antibiotics[J]. Lancet, 1997,349(9049):418-42...
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