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Acetophenone-substituted straight-chain sesqui derivative and application thereof in inhibiting basterium drug resistance

A technology of acetophenone and derivatives, applied in the field of pharmacy, can solve the urgent need for new antibacterial agents and other problems

Inactive Publication Date: 2013-11-13
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some new advances have been made in the research of antibiotics in the past decade, the need for new antibacterial agents to suppress bacterial resistance is still quite urgent

Method used

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  • Acetophenone-substituted straight-chain sesqui derivative and application thereof in inhibiting basterium drug resistance
  • Acetophenone-substituted straight-chain sesqui derivative and application thereof in inhibiting basterium drug resistance
  • Acetophenone-substituted straight-chain sesqui derivative and application thereof in inhibiting basterium drug resistance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of phenylpolyene sesquiterpene derivatives compounds 1 and 2 by ferulocarp

[0040] 2.0 kg of root parts of dried plant Ferula ferulaeoides (Steud.) Korov. were crushed and mixed with 20 times the amount of 95% ethanol at 45 o C soaking and extracting for 3 times, the extracts were combined and evaporated to dryness under reduced pressure to obtain extract, which was then extracted with dichloromethane 3 times, and evaporated to dryness under reduced pressure to obtain 400 g of extract. The sample was subjected to silica gel column chromatography, using 200-300 mesh silica gel (Qingdao Ocean Chemical Factory, China), petroleum ether-ethyl acetate (100:0 ~ 0:100) gradient elution, and silica gel thin-layer chromatography detection. Combine petroleum ether-ethyl acetate 70:30 eluted fractions, and repeatedly use 300-400 mesh silica gel column chromatography, the eluent is petroleum ether-acetone (85:15), to obtain compound 1 (22.0 mg); combine petro...

Embodiment 2

[0041] Embodiment 2 antibacterial experiment

[0042] Before the minimum inhibitory concentration (MIC) test, all test strains were inoculated on agar medium (Oxoid) at 37 o C cultured for 24 h. Control drugs Tetracycline, nor?oxacin, erythromycin and oxacillin were purchased from Sigma Chemical Co. The matrix was cation-adjusted broth (Mueller-Hinton broth, MHB; Oxoid), adjusted for Ca 2+ and Mg 2+ The concentration is 20 mg / L. Prepare the inoculum concentration of each Staphylococcus aureus strain (S. aureus) as 5×10 5 cfu / mL. Tetracycline and oxacillin were directly dissolved in the broth. Norfloxacin, erythromycin and the compound dshamirone were first dissolved in DMSO and then diluted into the broth to prepare 512 μg / mL as the initial concentration. The antibacterial activity of the control drug and compound dshamirone was determined by 96-well plate method. Add 125 μL of bacterial inoculum to all wells of the microplate, and o C for 18 h. The results were obse...

Embodiment 3

[0044] Example 3 Compound external pump and toxicity test

[0045] In the external pump inhibition experiment, the bacterial strain was cultured in broth for 24 hours, then centrifuged and precipitated, and the supernatant was removed, added to the buffer solution containing glucose, and diluted to the required concentration with an absorbance meter; Spectrophotometer, time scanning method was used to measure the fluorescence intensity, drug was added after 10 min in the administration group, and the scan was continued for 10 min; no drug was added in the control group, and the inhibitory effect of compounds 1 and 2 on the ethidium bromide efflux pump was observed.

[0046] Cell count Kit-8 (Dojindo, Japan) was used in the cytotoxicity test. Trypsinized HEK293 cells were cultured on a 96-well plate. After 24 hours, the cells were inoculated into the medium containing the drug at a specific concentration and cultured for 24 hours. CCK-8 reagent was added, and the OD450 was meas...

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Abstract

The invention belongs to the field of pharmacy, and relates to a benzene polyene sesquiterpene derivative and an application thereof in preparing an anti-resistant-bacteria medicine and preparation, and especially in preparing medicines and preparations used for inhibiting drug-resistant staphylococcus aureus. The benzene polyene sesquiterpene derivative provided by the invention comprises compounds 1 and 2, and is obtained by separation from a traditional Chinese medicine material asafoetida. As a result of test, the derivative has pharmacological activity against drug-resistant staphylococcus aureus. The compound 2 has a minimal inhibitory concentration (MIC) of 2mug / L against tetracycline-resistant staphylococcus aureus strain XU212 and methicillin-resistant staphylococcus aureus strain EMRSA-15, such that the activity is substantially better than control drugs tetracycline and oxacillin. For bacterium drug resistance, the compounds 1 and 2 show significant external pump inhibition effect against resistant staphylococcus aureus RN4220 with MsrA macrolide external pump protein and methicillin-resistant staphylococcus aureus EMRSA-16 with mecA gene. The derivative can be further used for preparing medicine preparations used for resisting external-pump drug-resistant staphylococcus aureus.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to an acetophenone-substituted straight-chain sesquiderivative and its application in the preparation of anti-drug-resistant bacteria drugs and preparations, especially the application of inhibiting drug-resistant Staphylococcus aureus. Background technique [0002] Antibiotic resistance of Staphylococcus aureus seriously threatens human health. Methicillin-resistant Staphylococcus aureus (MRSA) infection spreads all over the world, becoming the leading pathogen causing human infectious diseases worldwide, and can cause life-threatening diseases such as endocarditis, pneumonia, and toxic shock syndrome. In recent years, due to the widespread use and even abuse of antibiotics, the situation of bacterial drug resistance has become more and more urgent. Although some new advances have been made in the research of antibiotics in the past decade, the need for new antibacterial agents to suppress b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/32C07D301/32C07D307/33A61K31/365A61K31/336A61P31/04
Inventor 刘涛穆青谢惠琴西蒙．吉本斯
Owner FUDAN UNIV
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