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Penicillin modified epsilon-polylysine antibacterial peptide and preparation method thereof

A technology of polylysine and penicillin, which is applied in the direction of antibacterial drugs, antifungal agents, and medical preparations of non-active ingredients. It can solve the problems of limited antibacterial effect, complex synthesis, and rarely exert antibacterial properties. Enhanced performance, low manufacturing cost, and simple synthesis method

Pending Publication Date: 2022-03-11
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its limited antibacterial effect, it is difficult to use alone as a clinical antibacterial drug
However, the synthesis of existing ε-polylysine-derived drugs is relatively complicated, and most of them are used as drug carriers, adjuvants for gene therapy or linking fragments of drugs, and rarely exert their own antibacterial properties.

Method used

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  • Penicillin modified epsilon-polylysine antibacterial peptide and preparation method thereof
  • Penicillin modified epsilon-polylysine antibacterial peptide and preparation method thereof
  • Penicillin modified epsilon-polylysine antibacterial peptide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation method of the epsilon-polylysine-Dipenicillin of the present embodiment comprises the following steps:

[0046] (1) Dissolve 3.72g (0.01mol) of penicillin potassium, 3.09g of N,N'-dicyclohexylcarbodiimide and 3.46g of N-hydroxysuccinimide in 15ml of pH=5 hydrochloric acid dilute solution and tetrahydrofuran mixed solvent (pH = 5 dilute hydrochloric acid solution: tetrahydrofuran = 2:1; v / v), react at 4°C for 3 hours to obtain penicillin activated ester monomer, as follows;

[0047]

[0048] (2) Add 5 mL of tetrahydrofuran to the activated penicillin ester to dissolve, add 30 mL of pre-dissolved deionized aqueous solution containing 16.115 g of ε-polylysine, and mix for 12 hours to obtain the ε-polylysine-dipenicillin.

[0049] pass 1 H-NMR verifies the product structure, and the corresponding characteristic peaks of ε-polylysine-Dipenicillin can be obtained as figure 2 Shown: wherein the peak area ratio (66:5) of b-f and k-m is consistent with the ...

Embodiment 2

[0050] Embodiment 2: The determination of ε-polylysine-dipicillin minimum inhibitory concentration IC50 value

[0051] experimental method:

[0052] ε-polylysine-Dipenicillin source: Example 1

[0053] Determination by the micro-broth dilution method, firstly add the appropriate LB broth (sterilized by high pressure steam) into the 96-well plate, then the test sample (2mg / mL) obtained by lyophilization and the reference drug (penicillin, ε- Polylysine) solution (equal mass concentration) was added to the first well of each row of the 96-well plate, diluted by the double dilution method, and finally an equal volume of bacterial solution was inoculated into each well plate to obtain the concentration of each test group. The final drug concentrations were 500μg / mL, 250μg / mL, 125μg / mL, 62.5μg / mL, 31.25μg / mL, 16μg / mL, 8μg / mL. At the same time, two parallel blank control groups (that is, no sample added) were set up for the test, and incubated at a constant temperature of 37°C for 1...

Embodiment 3

[0056] Embodiment 3: Determination of hemolytic toxicity of ε-polylysine-Dipicillin

[0057] experimental method:

[0058] ε-polylysine-Dipenicillin source: Example 1

[0059] Adopt microdilution method to measure, at first configure the solution (2000 μ g / mL) of epsilon-polylysine-double penicillin and contrast drug (penicillin) with PBS buffer solution (pH=7.4), adopt double dilution method to half-dilution, then Add the same amount of blood cell PBS suspension to the sample solution to obtain the final drug concentrations of each test group as 1000 μg / mL, 500 μg / mL, 250 μg / mL, 125 μg / mL, 62.5 μg / mL, and use the same amount of PBS buffer And 0.1% Triton X-100 was added to the blood cell suspension to set up blank and positive control groups respectively. Incubate with repeated shaking for one hour. Centrifuge after culture, test the OD of each liquid supernatant 405 Value, and calculate the percentage of hemolysis in turn, the calculation formula is as follows:

[0060]...

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Abstract

According to the penicillin-modified epsilon-polylysine antibacterial peptide and the preparation method thereof, amino groups on epsilon-polylysine are combined with carboxyl groups of penicillin antibiotics, so that the penicillin-modified epsilon-polylysine antibacterial peptides connected with different numbers of small molecular penicillin antibiotics are prepared respectively; the epsilon-polylysine still has more side chain functional groups after being partially coupled, so that the synergistic medication effect can be realized by combining different medicines, such as clavulanic acid and nalidixic acid, and the epsilon-polylysine has a wider application range; the epsilon-polylysine is coupled with the hydrophobic penicillin drugs through good hydrophilicity and biocompatibility, the solubility of the hydrophobic drugs is improved, the antibacterial characteristics of the two substances are combined, the good antibacterial effect of penicillin antibiotics on common strains is kept, and the antibacterial activity of the penicillin antibiotics is improved. The broad-spectrum antibacterial effect of epsilon-polylysine is synergistically exerted, and the effective antibacterial range of the medicine is expanded; the synthesis route is simple, raw materials are easy to obtain, and the manufacturing cost is low.

Description

technical field [0001] The invention belongs to the technical field of biomedical polymers, and in particular relates to a penicillin-modified ε-polylysine antibacterial peptide and a preparation method thereof. Background technique [0002] Penicillin antibiotics are a class of antibiotics containing a β-lactam ring and a five-membered thiazole ring in their chemical structure. They were first discovered by British biochemist Fleming in 1928. By changing the chemical structure of the side chain group, penicillin antibiotics have a variety of different antibacterial spectrums and antibacterial effects, and are widely used in clinical treatment. However, due to the limitation of early cognition, the misuse and abuse of such antibiotics led to the continuous induction and accumulation of corresponding drug-resistant bacteria, which eventually led to a gradual decline in their efficacy. [0003] The ε-polylysine was first discovered by two Japanese chemists, Shoji Shima and He...

Claims

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Application Information

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IPC IPC(8): A61K31/785A61K31/198A61K31/43A61K47/55A61K31/424A61K31/4375A61P31/04A61P31/10
CPCA61K31/785A61K31/198A61K31/43A61K47/552A61K31/424A61K31/4375A61P31/04A61P31/10A61K2300/00
Inventor 周春才陈思锦
Owner TONGJI UNIV
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