| N-3-oxo-dodecanoyl-L-Homoserine lactoneNF-κB and AP-2 activator |
Sample solution is provided at 25 µL, 10mM.
Nature.2017 Jan 19;541(7637):417-420.
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- Purity = 98.00%
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Chemical structure
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| Cas No. | 168982-69-2 | SDF | Download SDF |
| Synonyms | 3-oxo-C12-HSL | ||
| Chemical Name | 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide | ||
| Canonical SMILES | CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O | ||
| Formula | C16H27NO4 | M.Wt | 297.4 |
| Solubility | ≤20mg/ml in DMSO;20mg/ml in dimethyl formamide | Storage | Store at -20°C |
| Physical Appearance | A crystalline solid | Shipping Condition | Evaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon request |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
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].
References:[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.
