Application of 24-membered macrocyclic Schiff base in preparation of drug for treating methicillin-resistant staphylococcus aureus infection

A staphylococcus infection, methicillin-resistant technology, applied in the field of medicine, can solve problems such as low affinity, and achieve the effects of simple steps, high purity, and reduced bacteriostatic concentration

Pending Publication Date: 2020-10-09
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PBP2a is a member of the penicillin-binding protein family, but its active site has a very low affinity for β-lactam antibiotics

Method used

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  • Application of 24-membered macrocyclic Schiff base in preparation of drug for treating methicillin-resistant staphylococcus aureus infection
  • Application of 24-membered macrocyclic Schiff base in preparation of drug for treating methicillin-resistant staphylococcus aureus infection
  • Application of 24-membered macrocyclic Schiff base in preparation of drug for treating methicillin-resistant staphylococcus aureus infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Synthesis of twenty-four-membered macrocyclic Schiff bases.

[0021] 1. Experimental equipment

[0022] The nuclear magnetic resonance spectrometer used Bruker's 500MHz nuclear magnetic resonance spectrometer, and the mass spectrometer used Thermo Fisher's LCQFleet liquid mass spectrometry instrument.

[0023] 2. Experimental drugs and reagents

[0024] 2,5-Dihydroxyterephthalaldehyde and p-phenylenediamine were purchased from Sarn Chemical Technology (Shanghai) Co., Ltd. The rest of the conventional reagents were of analytical grade.

[0025] 3. Experimental method

[0026] The synthesis of the 24-membered macrocyclic Schiff base adopts the method of solvent dilution. Specifically: take 0.83g of 2,5-dihydroxyterephthalaldehyde (5mmol) and dissolve it in 500mL of methanol solution, add 100mL of methanol solution with 0.54g of p-phenylenediamine (5mmol) dropwise under stirring conditions, After stirring at room temperature for 6 hours, an orange-yellow pr...

Embodiment 2

[0027] Example 2: Verification that the 24-membered macrocyclic Schiff base induces the core sequence of the MecA gene to form a G-quadruplex structure.

[0028] 1. Experimental equipment

[0029] The circular dichroism spectrometer was purchased from Applied Optical Physics, UK

[0030] 2. Experimental drugs and reagents

[0031] The MecA gene sequence was obtained from GeneBank, and its core sequence was selected as 5'-GATGGTAAAGGTTGGCAGG-3'. The DNA was purchased from Sangon Bioengineering (Shanghai) Co., Ltd., and trimethylaminomethane (Tris) was purchased from Huamei Bioengineering Company. The high-concentration stock solution of twenty-four-membered macrocyclic Schiff base is 20mM, dissolved in DMSO.

[0032] 3. Experimental method

[0033] System 1: Contains 10 μM MecA DNA and 10 mM Tris-HCl at a final concentration of 200 μL in total, and fills up the deficiency with distilled water.

[0034] System 2: Contains MecA DNA at a final concentration of 10 μM, Tris-HCl ...

Embodiment 3

[0038] Example 3: Verification that the 24-membered macrocyclic Schiff base reduces the minimum inhibitory concentration (MIC value) of methicillin-resistant Staphylococcus aureus.

[0039] 1. Experimental equipment

[0040] The McFarney turbidimeter was purchased from Beijing Tianan United Technology Co., Ltd., and the water-proof constant temperature incubator was purchased from Shanghai Shuli Instrument Co., Ltd.

[0041] 2. Strains

[0042] Collect Staphylococcus aureus strains isolated from the microbiology laboratory of a hospital from July to December 2018, and exclude repeated strains from the same patient. ) identified methicillin-resistant Staphylococcus aureus strains, and collected 17 strains in total. The quality control strain was Staphylococcus aureus ATCC29213, which was purchased from Guangdong Huankai Microbial Technology Co., Ltd.

[0043] 3. Experimental drugs and reagents

[0044] M-H broth powder was purchased from Oxoid Company in the UK, blood plate...

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Abstract

The invention discloses an application of 24-membered macrocyclic Schiff base in preparation of a drug for treating methicillin-resistant staphylococcus aureus infection. The 24-membered macrocyclic Schiff base is found to form a G-quadruplex structure with the core sequence of the MecA gene in the methicillin-resistant staphylococcus aureus through methods such as circular dichroism spectrum andWestern-Blot, so that the expression of the corresponding penicillin-binding protein PBP2a is inhibited. Pharmacological sensitivity experiments prove that the 24-membered macrocyclic Schiff base canreduce the minimum inhibitory concentration of methicillin-resistant staphylococcus aureus on oxacillin. When the use amount of the 24-membered macrocyclic Schiff base is 5 [mu] M, the minimum inhibitory concentration of methicillin-resistant staphylococcus aureus can be reduced to 0.5 [mu] g/mL to the minimum, and the effect of treating methicillin-resistant staphylococcus aureus infection by using beta-lactam drugs is achieved.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the application of a twenty-four-membered macrocyclic Schiff base in the preparation of a drug for treating methicillin-resistant Staphylococcus aureus infection. Background technique [0002] Scientists first isolated MRSA in 1961, and the strain spread rapidly in the 1990s and today causes infections across the globe. Methicillin-resistant Staphylococcus aureus is resistant to all other β-lactam antibiotics with similar structures to methicillin except for methicillin. Different mechanisms, such as enzymes and reduced membrane permeability, have different degrees of drug resistance to aminoglycosides, macrolides, tetracyclines, fluoroquinolones, sulfonamides, and rifampin. The clinical treatment of infections caused by Staphylococcus aureus poses great challenges. At present, it is generally believed that the drug resistance mechanism of methicillin-resistant Staphylococcus ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/395A61P31/04
CPCA61K31/395A61P31/04
Inventor 苑立博
Owner HENAN UNIVERSITY OF TECHNOLOGY
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