N-dodecanoyl-L-Homoserine lactone (Synonyms: C12-HSL) |
| رقم الكتالوجGC44355 |
N-dodecanoyl-L-Homoserine lactone (C12-HSL) هو جزيء يشير إلى النصاب (QS)
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 137173-46-7
Sample solution is provided at 25 µL, 10mM.
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N-dodecanoyl-L-Homoserine lactone is a small, diffusible signaling molecule involved in quorum sensing (QS), which can regulate gene expression and affect the cellular metabolism of bacteria [1-2]. The disruption of QS is considered a stimulating method for reducing bacterial pathogenicity and drug resistance [3]. The N-dodecanoyl-L-Homoserine lactone aptamer can be used to block the QS of Pseudomonas aeruginosa and inhibit the formation of its biofilm [4].
In vitro, N-dodecanoyl-L-Homoserine lactone (500nM; 2-5h) significantly reduced the number of spore germination and the length of hyphae of Galactomyces during polar growth, and inhibited the Ras1-cAMP-PKA signal transduction and MAPK pathway [5]. N-dodecanoyl-L-Homoserine lactone (4, 8, 16, 32, 64, 128, 256, 512 and 1024µg/ml; 18h) has antibacterial effects on Staphylococcus aureus, with MIC90 and MBC90 being 64 and 128µg/ml respectively. The doses of N-dodecanoyl-L-Homoserine lactone (64 and 128µg/ml; 24, 48h) showed dose- and time-dependent reduction in the cell viability of CHO and HeLa cells, with IC50 values of 256 and 512µg/ml for Hela cells and CHO cells respectively [6].
References:
[1] McClean KH, Winson MK, Fish L, et al. Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology (Reading). 1997;143 ( Pt 12):3703-3711.
[2] Lithgow JK, Wilkinson A, Hardman A, et al. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci. Mol Microbiol. 2000;37(1):81-97.
[3] Borges A, Sousa P, Gaspar A, Vilar S, Borges F, Simões M. Furvina inhibits the 3-oxo-C12-HSL-based quorum sensing system of Pseudomonas aeruginosa and QS-dependent phenotypes. Biofouling. 2017;33(2):156-168.
[4] Winson MK, 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. Proc Natl Acad Sci U S A. 1995;92(20):9427-9431.
[5] Lu X, Wang Y, Chen C, Feng Z, Huo Y, Zhou D. C12-HSL is an across-boundary signal molecule that could alleviate fungi Galactomyces's filamentation: A new mechanism on activated sludge bulking. Environ Res. 2022;204(Pt A):111823.
[6] Shahbandeh M, Moosazadeh Moghaddam M, Golmohammadi R, Mirnejad R. The antimicrobial effect of quorum sensing autoinducers of Pseudomonas aeruginosa, C12-HSL and C4-HSL, against MDR Staphylococcus aureus isolates. Comp Immunol Microbiol Infect Dis. 2022;81:101747.
| Cell experiment [1]: | |
Cell lines | Staphylococcus aureus isolates |
Preparation Method | Staphylococcus aureus isolates initial inoculum of 1.5×108c.f.u/ml was prepared and bacterial cultures were incubated with serial concentrations of N-dodecanoyl-L-Homoserine lactone (4, 8, 16, 32, 64, 128, 256, 512, and 1024µg/ml) in a shaking bath for 18h at 37°C. After 18h of incubation, bacterial turbidity was measured to an optical density at 600 nm (OD600) by spectrophotometer of each sample. The lowest concentrations that inhibited the growth of 50% and 99.9% of bacteria were considered as MIC and MBC, respectively. Each experiment was repeated at least three times. |
Reaction Conditions | 4, 8, 16, 32, 64, 128, 256, 512, and 1024µg/ml; 18h |
Applications | N-dodecanoyl-L-Homoserine lactone has antibacterial effects on S. aureus. The MIC90 and MBC90 values are 64 and 128μg/ml, respectively. |
References: | |
| Cas No. | 137173-46-7 | SDF | |
| المرادفات | C12-HSL | ||
| Chemical Name | N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide | ||
| Canonical SMILES | CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O | ||
| Formula | C16H29NO3 | M.Wt | 283.4 |
| الذوبان | 30mg/ml in DMSO, or in DMF | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 3.5286 mL | 17.6429 mL | 35.2858 mL |
| 5 mM | 705.7 μL | 3.5286 mL | 7.0572 mL |
| 10 mM | 352.9 μL | 1.7643 mL | 3.5286 mL |
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- Purity: >99.00%
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