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Merck
CN

804231

Sigma-Aldrich

2-溴-N-[(3S)-四氢-2-氧代-3-呋喃基]-苯乙酰胺

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别名:
AbaR, QscR inhibitor
经验公式(希尔记法):
C12H12BrNO3
分子量:
298.13
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.22

形式

solid

储存温度

−20°C

SMILES字符串

O=C(OCC1)[C@@]1([H])NC(CC2=C(Br)C=CC=C2)=O

InChI

1S/C12H12BrNO3/c13-9-4-2-1-3-8(9)7-11(15)14-10-5-6-17-12(10)16/h1-4,10H,5-7H2,(H,14,15)/t10-/m0/s1

InChI key

MMJSTOMMZPSKSQ-JTQLQIEISA-N

应用

The following AHL is a phenylacetanoyl L-homoserine lactone (PHL), a class of compounds found to strongly modulate many LuxR-type receptors. It is an active inhibitor of the putative LuxR-type receptor in Acinetobacter baumannii – AbaR and the quorum-sensing repressor in P. aeruginosa – QscR.

象形图

Exclamation mark

警示用语:

Warning

危险声明

预防措施声明

危险分类

Acute Tox. 4 Oral

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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Margrith E Mattmann et al.
Chembiochem : a European journal of chemical biology, 12(6), 942-949 (2011-03-03)
Bacteria can coordinate group behavior using chemical signals in a process called quorum sensing (QS). The QS system in the opportunistic pathogen Pseudomonas aeruginosa is largely governed by the LasR receptor and its cognate chemical signal, N-(3-oxo)-dodecanoyl L-homoserine lactone (OdDHL).
Grant D Geske et al.
Chemical Society reviews, 37(7), 1432-1447 (2008-06-24)
Bacteria are capable of "communicating" their local population densities via a process termed quorum sensing (QS). Gram-negative bacteria use N-acylated l-homoserine lactones (AHLs), in conjunction with their cognate LuxR-type receptors, as their primary signalling circuit for QS. In this critical
Danielle M Stacy et al.
ACS chemical biology, 7(10), 1719-1728 (2012-08-03)
Many bacterial pathogens use quorum sensing (QS) to control virulence. As a result, the development of methods to intercept QS has attracted significant interest as a potential anti-infective therapy. Acinetobacter baumannii has emerged as a pan-drug-resistant pathogen and displays a
Margrith E Mattmann et al.
Bioorganic & medicinal chemistry letters, 18(10), 3072-3075 (2007-12-18)
The transcription factor QscR is a regulator of quorum sensing in Pseudomonas aeruginosa and plays a role in controlling virulence in this prevalent opportunistic pathogen. This study outlines the discovery of a set of synthetic N-acylated homoserine lactones that are

相关内容

Our laboratory pursues research at the chemistry-microbiology interface. We are deeply interested in the mechanisms by which bacteria sense each other, their environment, and the eukaryotic hosts on which and in which they may reside. One prominent pathway that we study is called quorum sensing, which allows bacteria to assess their local population density and initiate group behaviors at high cell (or “quorate”) density. This pathway allows, for example, many pathogens to amass in large populations prior to attacking their hosts. Bacteria use chemical signals for quorum sensing, and it is the concentration of these signals in a given environment that alerts the bacteria to their current cell number. We are interested in the structures of these signals and how we can reengineer them to either ablate or amplify quorum-sensing networks. Through synthesis and systematic screening, we have identified critical structural features of these signals and non-native functionality that we can install into the signals to tune their function. Thereby, we have developed non-native molecules that strongly inhibit or activate quorum-sensing pathways and modify infection processes. These compounds represent useful tools to explore the role of quorum sensing in many biological processes. We are applying them to both study fundamental aspects of quorum sensing pathways, and examine different types of infections in animals and plants.

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