N-3-oxo-dodecanoyl-L-Homoserine lactone

N-3-oxo-dodecanoyl-L-Homoserine lactone

Catalog Number:
FC01366453APE
Mfr. No.:
APE-C4107
Price:
$299
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          Background

          N-3-oxo-dodecanoyl-L-Homoserine lactone is one of the acylhomoserine lactones (AHLs) frequently identified in extracts of respiratory secretions from cystic fibrosis patients infected with pseudomonas aeruginosa and species of the Burkholderia cepacia complex [2]. Quorum sensing system is a system used by bacteria for controlling gene expression in response to increasing cell density and therefore control behavior on a community-wide scale. Cell-cell communication can occur within and between bacterial species and a variety of different molecules can be used as signals, such as N-acyl homoserine lactones (AHL) in Gram-negative bacteria [1]. N-3-oxododecanoyl homo-serine lactone (3-O-C12-HSL), the Pseudomonas autoinducer, is a small lipid-soluble molecule that is essential in the regulation of many P. aeruginosa virulence factors. In 16HBE cells or L828 fibroblasts, 3-O-C12-HSL significantly increased the levels of IL-8 mRNA and protein. Also, supernatants from 3-O-C12-HSL-stimulated cells induced neutrophil chemotaxis. The severe lung damage that accompanied P. aeruginosa infections was caused by an exuberant neutrophil response stimulated by 3-O-C12-HSL-induced IL-8 [3].

          [1]. Henke JM, Bassler BL. Bacterial social engagements. Trends Cell Biol. 2004 Nov;14(11):648-56.
          [2]. Chambers CE, Visser MB, Schwab U, et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett. 2005 Mar 15;244(2):297-304.
          [3]. Smith RS, Fedyk ER, Springer TA, et al. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-kappa B and activator protein-2. J Immunol. 2001 Jul 1;167(1):366-74.

      • Properties
        • Categories
          NF-κB and AP-2 activator
          Alternative Name
          3-oxo-C12-HSL; 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
          CAS Number
          168982-69-2
          Molecular Formula
          C16H27NO4
          Molecular Weight
          297.4
          Appearance
          A crystalline solid
          Purity
          98.00%
          Solubility
          ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide
          Storage
          Store at -20°C
          SMILES
          CCCCCCCCCC(=O)CC(=O)N[[email protected]]1CCOC1=O

          * For Research Use Only

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