N-dodecanoyl-L-Homoserine lactone Exclusive

Cayman Chemical Item Number 10011203

dDHL; C12-HSL (CAS 137173-46-7)

N-dodecanoyl-L-Homoserine lactone (CAS 137173-46-7)

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Description

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 LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-dodecanoyl-L-Homoserine lactone (C12-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.1,2,3 In addition to regulating bacterial functions, C12-HSL activates NF-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β), and IL-8, while other lactones do not.4 In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells.5 It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-Homoserine lactone (Catalog No. 10007895), which is produced at different times in biofilm development6 and has different cellular effects.5

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. J Bacteriol 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. Mol Microbiol 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 Gomi, K., Kikuchi, T., Tokue, Y., et al. Mouse and human cell activation by N-dodecanoyl-DL-homoserine lactone, a Chromobacterium violaceum autoinducer. Infect Immun 74(12) 7029-7031 (2006).

5 Kristiansen, S., Bjarnsholt, T., Adeltoft, D., et al. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS 116 361-371 (2008).

6 Huang, Y., Ki, J., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME J 1-9 (2008).

Synonyms
  • dDHL
  • C12-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​dodecanamide
CAS Number 137173-46-7
Molecular Formula C16H29NO3
Formula Weight 283.4
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCCCCCC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)​17-14-12-13-20-16(14)​19/h14H,2-13H2,1H3,(H,17,18)​/t14-/m0/s1
InCHI Key
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WILLZMOKUUPJSL-AWEZNQCLSA-N

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Size Price Quantity Subtotal
5 mg $30.00 $0.00
10 mg $57.00 $0.00
25 mg $135.00 $0.00
50 mg $240.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-17. Prices are subject to change without notice.

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