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Bacterial quorum sensing inhibitors as well as preparation method and application thereof

A technology of isomers and medicinal salts, applied in the field of bacterial quorum sensing inhibitors and its preparation, can solve the problems of reducing the antibacterial efficiency of antibiotics and increasing drug-resistant strains, achieving good economy, simple preparation method, and good application prospects Effect

Active Publication Date: 2019-03-22
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The abuse of antibiotics leads to the increase of drug-resistant strains and also reduces the antibacterial efficiency of existing antibiotics

Method used

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  • Bacterial quorum sensing inhibitors as well as preparation method and application thereof
  • Bacterial quorum sensing inhibitors as well as preparation method and application thereof
  • Bacterial quorum sensing inhibitors as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Synthetic purification and structure identification of embodiment 1 pyrrolidone derivative General method:

[0100] Take 5.0g of levulinic acid in a three-necked flask, add 10ml of petroleum ether, 2ml of 40% HBr, stir in an ice bath, and protect with nitrogen; take another 10ml of bromine in 20ml of petroleum ether, drop by drop with a normal pressure separatory funnel In the three-necked bottle (about 2 drops / second) drip completely in 35 minutes, and rinse with 20ml of petroleum ether. Heated to 50°C for about 30 minutes, condensed to reflux. After reacting for one hour, a large amount of white solids precipitated. After cooling, they were washed with 10 ml of water, 10 ml of sodium thiosulfate solution (0.5 mol / L), and 10 ml of saturated brine, dried, and rotary evaporated to obtain a crude product. Take about 11.5 g of the obtained crude product, add 75 ml of 98% concentrated sulfuric acid, heat to 120° C., condense and reflux. After reacting for 20 minutes, cool...

Embodiment 2

[0109] Example 2 The effect of pyrrolidone derivatives on inhibiting the growth of Pseudomonas aeruginosa PAO1 and the output of pyocyanin:

[0110]Experimental method: Pseudomonas aeruginosa (CGMCC 1.12483, PAO1) was inoculated into LB medium, cultured overnight at 37° C. to obtain Pseudomonas aeruginosa PAO1 bacterial liquid. 3 mL of bacterial liquid was dispensed into test tubes, and 3 μM of each pyrrolidone derivative was added. After culturing for 1, 3, 5, 7, 9, 15, and 25 hours, the absorbance at 620 nm was measured respectively. It can be seen that these compounds have no inhibitory effect on the growth and reproduction of Pseudomonas aeruginosa (3 of which are positive control drugs).

[0111] After that, the original bacterial solution was diluted to OD 620 =0.05, continue culturing for three hours to the logarithmic growth phase. Dilute again to OD 620 = 0.05. The culture solution was dispensed into test tubes by 5 mL. Add 5 μM of each pyrrolidone derivative co...

Embodiment 3

[0113] Example 3 Inhibition of pyrrolidone derivatives to Pseudomonas aeruginosa PAO1 proteolytic enzyme:

[0114] Inoculate Pseudomonas aeruginosa into LB medium and culture overnight at 37°C to obtain Pseudomonas aeruginosa PAO1 bacterial liquid. The bacterial solution was dispensed into 5 mL test tubes, and after adding 5 μM of each pyrrolidone derivative, cultured in a 37° C. incubator for 8 hours. Afterwards, filter 100 μL of the culture solution, dispense it into EP tubes, add 5 mg of azocasein substrate, 1 mL of Tris buffer (10 mM), CaCl 2 (1 mM). The OD440 and OD620 values ​​of the solution were measured after the culture solution was quenched and centrifuged. The expression level of proteolytic enzymes is represented by OD440 / OD620, and the inhibition rate is calculated by comparing the results of the experimental group with the blank control. image 3 It can be seen that these compounds have different degrees of inhibition (58.2%-78.5%) on PAO1 proteolytic enzyme....

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Abstract

The invention provides bacterial quorum sensing inhibitors as well as a preparation method and an application thereof, and belongs to the technical field of medical chemistry. The bacterial quorum sensing inhibitors mainly comprise alpha-pyridoin derivatives with novel structures; research proves that the derivatives can remarkably reduce expression of related pathogenic factors and bacterial virulence in a range of not inhibiting growth of pathogenic bacteria, so that the derivatives can be used as the bacterial quorum sensing inhibitors for preventing and controlling bacterial infection of aquorum sensing system. Meanwhile, the preparation method of the compounds is simple, reaction conditions are mild, raw materials are cheap and easily available, the various compounds with brand-new structure can be prepared and obtained rapidly on a large scale, and the method has good economy and large-scale industrial production value.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a bacterial quorum sensing inhibitor and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] The abuse of antibiotics leads to the increase of drug-resistant strains and also reduces the antibacterial efficiency of existing antibiotics. Therefore, the establishment of new antibacterial therapy is very urgent. It is generally believed that the most promising therapy is quorum sensing (QuorumSensing, QS) suppression therapy. The mechanism of action of traditional antibiotic therapy is completely different: QS therapy ...

Claims

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Application Information

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IPC IPC(8): C07D207/44C07D405/06A61P31/04A61K31/4015A61K31/4025
CPCA61P31/04C07D207/44C07D405/06Y02A50/30
Inventor 马淑涛刘志阳
Owner SHANDONG UNIV
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