Ruthenium polypyridine complex with triphenylphosphine structure, and preparation method and application thereof

A technology of triphenylphosphine and ruthenium polypyridine, which is applied in the field of ruthenium polypyridine complexes and their preparation, can solve the problems such as the reduction of antibiotic sensitivity, and achieves increased sensitivity, enhanced transmembrane effect and retention effect, and improved biological activity. good effect

Active Publication Date: 2021-09-03
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It is precisely because of this drug resistance mechanism of bacteria that the bacteria are less sensitive to anti

Method used

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  • Ruthenium polypyridine complex with triphenylphosphine structure, and preparation method and application thereof
  • Ruthenium polypyridine complex with triphenylphosphine structure, and preparation method and application thereof
  • Ruthenium polypyridine complex with triphenylphosphine structure, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Preparation of intermediate formula Ⅰ-c:

[0030] 4-(4-bromobutoxy)benzaldehyde (0.6g, 2.3mmol), PPh 3 (3.6g, 13.8mmol), KI (38mg, 0.23mmol) (1.7g, 12mmol) in CH 3 The mixture in CN (15 mL) was heated to 90 °C under argon, and the resulting mixture was refluxed until TLC showed no starting material (ca. 36 h). After cooling to room temperature, the mixture was extracted with water / ethyl acetate (20 mL / 20 mL), the organic phases were combined, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (dichloromethane:methanol = 20:1 as eluent) to obtain the desired intermediate. Yield: 32.5%.

[0031] (2) Preparation of ligand TPP:

[0032] A mixture of 1,10-phenanthroline-5,6-dione (1.0g, 4.6mmol), intermediate formula Ⅰ-c (2.4g, 4.6mmol), ammonium acetate (7.1g, 91mmol) in ethanol ( 20 mL) solvent and heated to reflux for 10 hours. The cooled solution was diluted with water and neu...

Embodiment 2

[0045] In vitro antibacterial activity test

[0046] (1) Determination of MIC by micro-double dilution method: culture Staphylococcus aureus Newman strain in TSB medium until OD 600 reach 1. Dilute the number of bacterial cells to approximately 5×10 with fresh TSB medium 6 CFU / mL (OD 600 = 0.05). Subsequently, 50 μL of different concentrations of ruthenium complexes were added to 200 μL of the bacterial suspension. At this time, the final drug concentration in each well is from left to right: 250, 125, 62.5, 31.3, 15.6, 7.8, 3.9, 2.0, 1.0, 0.5 μg / mL; After further incubation for 20 hours at °C, the results were observed. Observe the turbid situation of the orifice plate, wherein the minimum drug concentration corresponding to the clear administration hole is the MIC (minimum inhibitory concentration).

[0047] figure 1 Among them, the bacteriostatic effect of complexes Ru-1~Ru-4 on Staphylococcus aureus was judged by observing the turbidity of the orifice plate, and the...

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Abstract

The invention belongs to the technical field of antibacterial medicines, and particularly relates to a ruthenium polypyridine complex with a triphenylphosphine structure, and a preparation method and application thereof. According to the ruthenium polypyridine complex with the triphenylphosphine structure, due to the fact that the ruthenium polypyridine complex contains metal ions and is charged, compared with traditional small organic molecules, the transmembrane effect and the retention effect are enhanced, and modification of different ligands can be carried out through the multi-coordination configuration of the metal complex, so the effect of better biological activity is achieved. Tests prove that the ruthenium polypyridine complex with the triphenylphosphine structure can effectively inhibit the growth of staphylococcus aureus and the formation of a biological membrane of the staphylococcus aureus when the content of the ruthenium polypyridine complex is 1.0-2.0 [mu]g/mL, and the ruthenium complex does not have the tendency of triggering the drug resistance of bacteria, and improves the sensitivity of the staphylococcus aureus to aminoglycoside antibiotics obviously.

Description

technical field [0001] The invention belongs to the technical field of antibacterial medicine, in particular to a ruthenium polypyridine complex with a triphenylphosphine structure and its preparation method and application. Background technique [0002] Staphylococcus aureus (S.aureus) is the most common pathogenic bacterium in clinical infectious diseases, which can cause infections in skin and soft tissues, blood system and lower respiratory tract, etc. Membranous enteritis, pneumonia and sepsis, etc. In recent years, the treatment of such infections has become more difficult due to the emergence of drug-resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA), which has severe resistance to many antibiotics. [0003] Biofilms, also known as biofilms, are composed of extracellular polymeric substances (EPS), a thin mucus layer secreted by microorganisms, forming a hydrogel or matrix that protects the microorganisms from external influences. Under nor...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P31/04
CPCC07F15/0053A61P31/04Y02A50/30
Inventor 王静廖向文王金涛
Owner JIANGXI SCI & TECH NORMAL UNIV
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