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804347

Sigma-Aldrich

3-nitro-N-[(3S)-tetrahydro-2-oxo-furanyl]-Benzeneacetamide

Synonym(s):

LasR inhibitor, LuxR activator

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About This Item

Empirical Formula (Hill Notation):
C12H12N2O5
CAS Number:
942296-29-9
Molecular Weight:
264.23
UNSPSC Code:
12352200
NACRES:
NA.22

form

solid

storage temp.

−20°C

Application

PHL has varied activity depending on species, for example serving as either a strong LuxR-type receptor activator (e.g.: of LuxR in V. fischeri and of ExpR1 and ExpR2 in Pectobacterium carotovora) or a strong inhibitor (e.g.: of LasR in P. aeruginosa)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Andrew G Palmer et al.
Chembiochem : a European journal of chemical biology, 12(1), 138-147 (2010-12-15)
Many bacteria use quorum sensing (QS) to regulate cell-density dependent phenotypes that play critical roles in the maintenance of their associations with eukaryotic hosts. In Gram-negative bacteria, QS is primarily controlled by N-acylated L-homoserine lactone (AHL) signals and their cognate
Grant D Geske et al.
Journal of the American Chemical Society, 129(44), 13613-13625 (2007-10-12)
Bacteria use a language of low molecular weight ligands to assess their population densities in a process called quorum sensing. This chemical signaling process plays a pivotal role both in the pathogenesis of infectious disease and in beneficial symbioses. There

Articles

Quorum Sensing Modulators

Quorum sensing is a chemical communication mechanism used by many common bacteria to initiate group behaviors. It plays an important role in the establishment of infection by pathogens and in mediating certain symbioses.

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Blackwell Group – Professor Product Portal

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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