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Antimicrobial compositions and uses

A composition, coating composition technology, applied in the direction of drug combination, application, compound of elements of group 4/14 of the periodic table, etc., can solve the problem of unspecified utility and the like

Inactive Publication Date: 2011-10-12
奥斯陆第一大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hornfeldt and Gronowitz in Arkiv foer Kemi, 1963, 21(22) , 239-257 describe the synthesis of other thiophenones without specifying their utility

Method used

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  • Antimicrobial compositions and uses
  • Antimicrobial compositions and uses
  • Antimicrobial compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] This example relates to the synthesis of thiophenones. Compound codes (eg Thio101) correspond to those described in Table 1.

[0057] Thio101 and Thio102

[0058] (E)-5-bromomethylenethiophen-2(5H)-one and (Z)-5-bromomethylenethiophen-2(5H)-one. Acetyl bromide (0.5 mL) was added dropwise to 5-formyl-2-methoxythiophene at 0 °C 1 (142mg) CDCl 3 (1.0 mL) solution. The mixture was stirred at 0°C for 1.5 hours, then evaporated. The crude product was purified by flash chromatography using hexane / ethyl acetate (5:1) as eluent. Yield of (E)-5-bromomethylenethiophen-2(5H)-one: 9 mg. Yield of (Z)-5-bromomethylenethiophen-2(5H)-one: 86 mg. The compounds were characterized by mass spectrometry and NMR.

[0059] Thio103

[0060] (Z)-5-Chloromethylenethiophen-2(5H)-one. Acetyl chloride (2 mL) was added to 5-formyl-2-methoxythiophene 1 (142mg). The mixture was stirred overnight at room temperature and then evaporated. The crude product was purified by flash chromatography...

Embodiment 2a

[0100] This example illustrates the effect of thiophenones on biofilm formation of various bacteria. Biofilm formation was measured according to the static biofilm model and the vibrating biofilm model, and it was found that various thiophenones tested either inhibited or prevented biofilm formation.

[0101] According to the static biofilm model, the specified thiophene 200 μmol / L was dissolved in 500 μl absolute ethanol and applied to the wells of a standard 24-well microtiter plate. Ethanol was evaporated from the wells in a laminar flow sterile bench at room temperature, leaving a coating of thiophenone in the wells. Bacterial samples are then added to the wells and incubated for a given period of time. After incubation, the percentage of bacteria remaining was assessed by safranin staining of the biofilm. Bound safranin was released by acetic acid and optical density was measured in a Synergy HT Multi-Detection Microplate Reader and compared to controls. The results ar...

Embodiment 2b

[0110] This example illustrates the effect of additional thiophenes on biofilm formation and planktonic growth of various bacteria.

[0111] Planktonic growth was determined in "low binding plates" where bacteria formed the least amount of biofilm. Quantities were determined by optical density measurements at 600 nm.

[0112] S. epidermidis biofilm formation was measured in static cultures in microtiter plate wells, or according to the Calgary method (The Calgary biofilm devices: New technology for rapid determination of antibiotic susceptibilities of bacterial biofilms. Ceri et al., J Clin Microbiol 1999:37:1771-1776) measured biofilm formation of Vibrio harveyi (V. harveyi) in static cultures on "peggs". In both cases, safranin staining was used and optical density was measured at 530 nm to quantify biofilm mass.

[0113] Thio401

[0114]

[0115] (Z)-4-((5-(bromomethylene)-2-oxo-2,5-dihydrothiophen-3-yl)methoxy)-4-oxobutanoic acid

[0116] The compound was synthesi...

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Abstract

An agent comprising the compound according to general formula (I) wherein R1, R2, R3 and R4 are each independently H or a substituent, and wherein at least one of R1, R3 and R4 is halogen, cyano, cyanate, thiocyanate or C1-C6 haloalkyl.

Description

[0001] The present invention relates to compounds and polymers comprising such compounds for use as antimicrobial agents, more particularly for blocking or interfering with quorum sensing microbial communication and / or preventing or inhibiting biofilm formation. Background technique [0002] Microorganisms, especially bacteria, are known to form biofilms under the combined conditions of bacteria, moisture, nutrients and suitable surfaces. Biofilm formation and biofouling cause problems and economic losses in domestic, industrial and health sectors. Various industrial processes and installations, such as underwater equipment and ships, various mechanical industries, petroleum processing and manufacturing, food and beverage industry, pharmaceutical industry, water systems, cooling towers, heat exchangers, chain lubrication systems, etc. may be affected. Biofilms can also cause problems with medical devices and implants and cause a variety of human and animal infections. It is o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/10A61K31/385C07D333/32A61P31/02C07F7/18C08F290/14
CPCA01N43/10A01N55/00A61K31/385C07D333/32C07F7/1804C08F228/06A61P31/00A61P31/02C08F220/1804C08F220/382A01N25/34A01N2300/00C08F212/08C08F128/00
Inventor 安妮·阿姆达尔·舍尔托尔·本尼切杰西卡·隆-斯腾卢德扬·斯卡拉姆斯塔达
Owner 奥斯陆第一大学