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Ruthenium polypyridine complex with triethylamine structure as well as preparation method and application of ruthenium polypyridine complex

A technology of ruthenium polypyridine complexes, applied in the field of ruthenium polypyridine complexes and their preparation, can solve the problems of difficult infection treatment, achieve the effects of inhibiting hemolysis, reducing red blood cell hemolysis, enhancing transmembrane effect and retention effect

Active Publication Date: 2022-07-15
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, this infection has become more difficult to treat due to the emergence of resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA), which is severely resistant to many antibiotics

Method used

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  • Ruthenium polypyridine complex with triethylamine structure as well as preparation method and application of ruthenium polypyridine complex
  • Ruthenium polypyridine complex with triethylamine structure as well as preparation method and application of ruthenium polypyridine complex
  • Ruthenium polypyridine complex with triethylamine structure as well as preparation method and application of ruthenium polypyridine complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Preparation of intermediate formula I-c:

[0026] Combine 4-(4-bromobutoxy)benzaldehyde (0.7 g, 2.75 mmol), triethylamine (3.8 g, 27.5 mmol), KI (45 mg, 0.275 mmol) in CH 3 The mixture in CN (15 mL) was heated to 60 °C under argon and the resulting mixture was refluxed until TLC showed no starting material (about 72 h). After cooling to room temperature, the mixture was extracted with water / dichloroethane (20 mL / 20 mL), the organic phases were combined, and the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (dichloromethane:methanol=3:1 as eluent) to yield the desired intermediate. As a dark brown solid, yield: 56%.

[0027] (2) Preparation of ligand NNN:

[0028] A mixture of 1,10-o-phenanthroline-5,6-dione (0.4 g, 2.01 mmol), intermediate formula I-c (0.7 g, 2.01 mmol), ammonium acetate (3.1 g, 40.2 mmol) in ethanol (15 mL) was heated to reflux in solvent for 10 hours. The coo...

Embodiment 2

[0037] Hemolysis test

[0038] (1) Compounds were dissolved in DMSO and incubated with Staphylococcus aureus Newman strain cultured in TSB medium until OD 600 reach 1. The bacterial liquid was sucked into the EP tube, and the centrifuge was rotated at 2500 r / min for 1 minute. Fresh red blood cells were separated from the rabbit blood by centrifugation, washed three times with PBS, and then the centrifuged rabbit blood, PBS and the supernatant of the bacterial solution were added to the EP tube. Incubate in a water bath for 30 min at 37°C, and then observe the results.

[0039] figure 2 Among them, the hemolysis inhibitory effect of the complexes Ru-1 to Ru-3 on Staphylococcus aureus was judged by observing the color of the supernatant, and the lighter the color of the supernatant blood, the stronger the inhibition of hemolysis. The test results show that the compound Ru-3 can significantly inhibit the production of Staphylococcus aureus toxin at the concentration of 0.5MI...

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Abstract

The invention discloses a ruthenium polypyridine complex with a triethylamine structure as well as a preparation method and application of the ruthenium polypyridine complex. The complex contains metal ions and is charged, so that compared with traditional small organic molecules, the complex has the advantages that the bacterial cell membrane penetrating capacity and retention effect of the complex are enhanced, and the metal complex can be modified by different ligands due to the multi-coordination configuration of the metal complex, so that the biological activity of the metal complex is higher. Tests prove that the ruthenium polypyridine complex with the triethylamine structure can effectively reduce the hemolysis effect of toxins released by staphylococcus aureus on red blood cells, and the ruthenium complex has no tendency to trigger drug resistance of bacteria and can significantly improve the sensitivity of staphylococcus aureus to aminoglycoside antibiotics.

Description

technical field [0001] The invention belongs to the technical field of antibacterial medicine, and in particular relates to a ruthenium polypyridine complex having a triethylamine structure and a preparation method and application thereof. Background technique [0002] Staphylococcus aureus (S. aureus) is one of the most common pathogens of clinical infectious diseases, which can cause infections in multiple parts of the skin and soft tissues, blood system and lower respiratory tract, resulting in a series of diseases, such as pericarditis, pseudo Membranous colitis, pneumonia and sepsis. In recent years, due to the emergence of drug-resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA), which are severely resistant to many antibiotics, the treatment of such infections has become increasingly difficult. [0003] Hemolysis refers to the phenomenon that the cell membrane of red blood cells is damaged and ruptured by physical factors, chemical factors, b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P31/04A61P7/00
CPCC07F15/0053A61P31/04A61P7/00Y02A50/30
Inventor 廖向文黄紫莹王金涛宋允王佩
Owner JIANGXI SCI & TECH NORMAL UNIV
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