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

Cayman Chemical Item Number 10007895

3-oxo-C12-HSL (CAS 168982-69-2)

N-3-oxo-dodecanoyl-L-Homoserine lactone (CAS 168982-69-2)

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Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1 A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules.1 N-3-oxo-dodecanoyl-L-homoserine lactone (3-oxo-C12-HSL) is one of the AHLs frequently identified in extracts of respiratory secretions from cystic fibrosis patients infected with P. aeruginosa and/or strains of the B. cepacia complex.2 3-oxo-C12-HSL activates the transcription factors NF-κB and AP-2 to induce interleukin-8 production in human lung fibroblasts and epithelial cells, possibly contributing to the neutrophil infiltration and inflammation found in P. aeruginosa infections.3

1 Henke, J.M., and Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004).

2 Chambers, C.E., Visser, M.B., Schwab, U., et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett 244 297-304 (2005).

3 Smith, R.S., Fedyk, E.R., Springer, T.A., 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-κB and activator protein-2. J Immunol 167 366-374 (2001).

Synonyms
  • 3-oxo-C12-HSL
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​dodecanamide
CAS Number 168982-69-2
Molecular Formula C16H27NO4
Formula Weight 297.4
Formulation A crystalline solid
Purity ≥98%
λmax 202, 250 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCCCC(=O)​CC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)​12-15(19)​17-14-10-11-21-16(14)​20/h14H,2-12H2,1H3,(H,17,19)​/t14-/m0/s1
InCHI Key
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PHSRRHGYXQCRPU-AWEZNQCLSA-N

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N-3-oxo-dodecanoyl-L-Homoserine lactone is available in the following screening library:

Size Price Quantity Subtotal
1 mg $23.00 $0.00
5 mg $104.00 $0.00
10 mg $184.00 $0.00
50 mg $805.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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