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N-octanoyl-L-Homoserine lactone

Catalog No.GC12708

N-octanoyl-L-Homoserine lactone Chemical Structure

A bacterial quorum sensing signal molecule

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5mg
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50mg
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Sample solution is provided at 25 µL, 10mM.

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Background

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. 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. N-

octanoyl-L-Homoserine lactone (C8-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism.1,2,3 The applications of this molecule include infection prevention and regulation of virulence in general and in cystic fibrosis.4,5

References
1. Kuo, A., Blough, N.V., and Dunlap, P.V. Multiple N-acyl-L-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri Journal of Bacteriology 176(24), 7558-7565 (1994).
2. Lithgow, J.K., Wilkinson, A., Hardman, A., et al. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci Molecular Microbiology 37(1), 81-97 (2000).
3. McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones Microbiology 143, 3703-3711 (1997).
4. Riedel, K., Hentzer, M., Geisenberger, O., et al. N-acylhomoserine-lactone-mediated communication between Pseudomonas aeruginosa and Burkholderia cepacia in mixed biofilms Microbiology 147, 3249-3262 (2001).
5. Winson, M.K., Camara, M., Latifi, A., et al. Multiple N-acyl-L-homoserine lactone signal molecules regulate production of virulence determinants and secondary metabolites in Pseudomonas aeruginosa Proceedings of the National Academy of Sciences of the United States of America 92, 9427-9431 (1995).

Chemical Properties

Cas No. 147852-84-4 SDF
Synonyms C8-HSL,OHL
Chemical Name N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide
Canonical SMILES CCCCCCCC(=O)C[C@H]1CCOC1=O
Formula C12H21NO3 M.Wt 227.3
Solubility DMF: 25 mg/ml,DMF:PBS(pH7.2) 1:2: 0.3 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 mg/ml Storage Store at -20°C
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.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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