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A method for improving the antibacterial properties and stability of cationic short peptides

A peptide antibacterial and cationic technology, applied in the field of antibacterial drugs, can solve the problems of poor stability and low antibacterial properties of cationic short peptides, and achieve the effects of improving stability, increasing action strength, and good antibacterial properties.

Inactive Publication Date: 2017-09-29
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention regulates the conformation and aggregation state of cationic short peptides by introducing guest molecules, and uses the cooperative assembly of the two to solve the problems of low antibacterial properties and poor stability of cationic short peptides

Method used

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  • A method for improving the antibacterial properties and stability of cationic short peptides
  • A method for improving the antibacterial properties and stability of cationic short peptides
  • A method for improving the antibacterial properties and stability of cationic short peptides

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 1. Preparation of cationic short peptide:

[0030] The synthesis of short cationic peptides can be achieved by a standard microwave-assisted solid-phase method: using amide resin as the substrate, using 9-fluorenylmethoxycarbonyl-protected L-amino acids as raw materials, and dried N,N-dimethylformamide (purity greater than 99.5%) is the reaction solvent, benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate is the coupling reagent, and N,N-diisopropylethylamine is The activator is used for amino acid condensation coupling reaction, and piperidine is used as the deprotection reagent to remove the 9-fluorenylmethoxycarbonyl group. The corresponding 9-fluorenyl moxycarbonyl-protected L-amino acid is sequentially coupled on the surface of the amide resin through repeated steps such as condensation coupling of L-amino acid and removal of the 9-fluorenyl moxycarbonyl protecting group.

Embodiment 1－1

[0032] Synthesis of tert-butyloxycarbonyl-4-azophenyl-L-phenylalanine: 2g tert-butyloxycarbonyl-4-amino-L-phenylalanine was dissolved in 200mL of glacial acetic acid, and then Quickly add 1.156g of nitrosobenzene and stir at room temperature for 8h. After the reaction was completed, 300 mL of saturated aqueous sodium bicarbonate solution was added to the reaction solution, and the above solution was extracted 3 times with ethyl acetate, and the ethyl acetate phase was collected and dried with anhydrous magnesium sulfate, and the obtained filtrate was filtered and concentrated, and the crude product was analyzed with a silica gel column. Purify. The developer dichloro:methanol=1:1 (volume ratio), and 1.64 g of a yellow solid product was obtained with a yield of 65%.

[0033] Synthesis of 9-fluorenylmethoxycarbonyl-4-azophenyl-L-phenylalanine: take 1g of tert-butyloxycarbonyl-4-azophenyl-L-phenylalanine obtained above and 50mL di Chloromethane was added into a 250mL round-bott...

Embodiment 1－2

[0036] Synthesis of KazoKazoK (molecular weight 903.5g / mol): As shown in Example 1-1, other conditions remain unchanged, and 9-fluorene is sequentially coupled on the amide resin according to the deprotection and coupling reaction steps described in Example 1-1 Methoxycarbonyl-tert-butyloxycarbonyl-L-lysine, 9-fluorenylmethoxycarbonyl-4-azophenyl-L-phenylalanine, 9-fluorenylmethyloxycarbonyl-tert-butyloxycarbonyl- L-lysine, 9-fluorenylmethoxycarbonyl-4-azophenyl-L-phenylalanine, 9-fluorenylmethoxycarbonyl-tert-butyloxycarbonyl-L-lysine. After the reaction is complete, add 3 mL of a mixed solution containing trifluoroacetic acid, anisole, water, and triisopropylsilane (volume ratio 88:5:5:2) to the reaction tube, and In a constant temperature shaker at 25°C, shake continuously for 3 h. After the reaction was completed, the filtered solution was added to 10 mL of glacial ether, and centrifuged for 3 minutes in a centrifuge with a rotation speed of 9,000 rpm to obtain a crude Ka...

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Abstract

The invention relates to a method for improving the antibacterial properties and stability of cationic short peptides, belonging to the technical field of antibacterial drugs. The method mainly includes the use of negatively charged polyanions to induce the assembly of cationic short peptides to form water-soluble cationic polymers, thereby enhancing the bonding ability between cationic short peptides and bacterial cell membranes, and effectively avoiding the traditional cationic short peptides on the surface of bacterial cell membranes. Migration, aggregation and other deficiencies ultimately greatly improve the antibacterial properties and stability of cationic short peptides. The advantage of this method lies in the purpose of improving the antibacterial properties and stability of cationic short peptides through simple and convenient steps. In addition, this method breaks through the limitations of traditional antimicrobial peptides such as long sequences, complex synthesis, high price, difficulty in batch synthesis, and poor stability, and greatly expands the range of antimicrobial peptides. It is expected to be used in the development, screening and application of peptide antibacterial drugs. play an important role.

Description

technical field [0001] The invention belongs to the technical field of antibacterial drugs, and in particular relates to an effective method for improving the antibacterial properties and stability of cationic short peptides. Background technique [0002] The disease hazards caused by bacterial infection seriously threaten human health and life safety. Although people have synthesized many antibacterial drugs (also known as antibiotics) to inhibit the activity of bacteria, a large number of clinical applications of antibiotics have significantly increased the drug resistance of bacteria (Stark, M.; Liu, L.-P.andDeber, C.M.Antimicrob .AgentsChemother., 2002,46,3585-3590.), some even produced multi-drug resistance, causing major public safety accidents. For example, the Methicillin-resistant Staphylococcus aureus (MRSA) infection that occurred in Europe and the United States in the 1950s quickly spread to the world, causing about 50 million people to be infected and more than...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06A61P31/04
Inventor 李敬芳李文吴立新
Owner JILIN UNIV
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