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Merck
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文件

804223

Sigma-Aldrich

3-oxo-C12-aniline

别名:

3-oxo-N-phenyl-Dodecanamide, LasR inhibitor, non-hydrolysable head group

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About This Item

经验公式（希尔记法）:
C18H27NO2
CAS号:
1186509-19-2
分子量:
289.41
分類程式碼代碼:
12352200
PubChem物質ID:
329768853
NACRES:
NA.22

形狀

solid

儲存溫度

−20°C

SMILES 字串

CCCCCCCCCC(CC(NC1=CC=CC=C1)=O)=O

InChI

1S/C18H27NO2/c1-2-3-4-5-6-7-11-14-17(20)15-18(21)19-16-12-9-8-10-13-16/h8-10,12-13H,2-7,11,14-15H2,1H3,(H,19,21)

InChI 密鑰

GYOZLHQAMICVMN-UHFFFAOYSA-N

應用

This analog mimics the native 3-oxo-C12 AHL signal utilized by Pseudomonas aeruginosa for quorum sensing, yet contains a non-hydrolysable aniline head group. 3-oxo-C12-aniline is a strong inhibitor of the LasR receptor in P. aeruginosa.

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

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N-（3-氧代十二烷酰基）-L-高丝氨酸内酯 quorum sensing signaling molecule

Sigma-Aldrich

O9139

N-（3-氧代十二烷酰基）-L-高丝氨酸内酯

Mutational Analysis of the Quorum-Sensing Receptor LasR Reveals Interactions that Govern Activation and Inhibition by Nonlactone Ligands.
Gerdt JP, et al.
Chemistry & Biology, 21, 1361-1369 (2014)
Design, synthesis and biological evaluation of abiotic, non-lactone modulators of LuxR-type quorum sensing
McInnis CE, and Blackwell HE
Bioorganic & Medicinal Chemistry, 19, 4812-4819 (2011)
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

相关内容

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.

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