N-dodecanoyl-L-Homoserine lactone
(Synonyms: 十二烷酰-L-高丝氨酸内酯,C12-HSL) 目录号 : GC44355
C12 quorum-sensing lactone
Cas No.:137173-46-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-Homoserine lactone which is produced at different times in biofilm development[6] 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. 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]. Gomi, K., Kikuchi, T., Tokue, Y., et al. Mouse and human cell activation by N-dodecanoyl-DL-homoserine lactone, a Chromobacterium violaceum autoinducer. Infection and Immunity 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. Acta Pathologica, Microbiologica, et Immunologica Scandinavica 116, 361-371 (2008).
[6]. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME Journal 1-9 (2008).
| Cas No. | 137173-46-7 | SDF | |
| 别名 | 十二烷酰-L-高丝氨酸内酯,C12-HSL | ||
| 化学名 | N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide | ||
| Canonical SMILES | CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O | ||
| 分子式 | C16H29NO3 | 分子量 | 283.4 |
| 溶解度 | 30mg/ml in DMSO, or in DMF | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.5286 mL | 17.6429 mL | 35.2858 mL |
| 5 mM | 0.7057 mL | 3.5286 mL | 7.0572 mL |
| 10 mM | 0.3529 mL | 1.7643 mL | 3.5286 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The bacterial quorum-sensing molecule, N-3-oxo-dodecanoyl-L-homoserine lactone, inhibits mediator release and chemotaxis of murine mast cells
Inflamm Res 2017 Mar;66(3):259-268.PMID:27896412DOI:10.1007/s00011-016-1013-3.
Objective: Bacterial colonization relies on communication between bacteria via so-called "quorum-sensing molecules", which include the acyl-homoserine lactone group. Certain acyl-homoserine lactones can modulate mammalian cell function and are thought to contribute to bacterial pathogenicity. Given the role of mast cells in host defense, we investigated the ability of acyl-homoserine lactones to modulate mast cell function. Methods: We utilized murine primary mast cell cultures to assess the effect of acyl-homoserine lactones on degranulation and cytokine release in response to different stimuli. We also assessed cell migration in response to chemoattractants. The effect of acyl-homoserine lactones in vivo was tested using a passive cutaneous anaphylaxis model. Results: Two of the tested quorum-sensing molecules, N-3-oxo-dodecanoyl-L-homoserine lactone and N-dodecanoyl-L-Homoserine lactone, inhibited IgE dependent and independent degranulation and mediator release from primary mast cells. Further testing of N-3-oxo-dodecanoyl-L-homoserine lactone, the most potent inhibitor and a product of Pseudomonas aeruginosa, revealed that it also attenuated chemotaxis and LPS induced cytokine production. In vivo, N-3-oxo-dodecanoyl-L-homoserine lactone inhibited the passive cutaneous anaphylaxis response in mice. Conclusion: The ability of N-3-oxo-dodecanoyl-L-homoserine lactone to stabilize mast cells may contribute to the pathogenicity of P. aeruginosa but could potentially be exploited therapeutically in allergic disease.
N-Acyl-Homoserine Lactone (AHL)-Mediated Microalgal-Bacterial Communication Driving Chlorella- Activated Sludge Bacterial Biofloc Formation
Environ Sci Technol 2022 Sep 6;56(17):12645-12655.PMID:35881886DOI:10.1021/acs.est.2c00905.
N-acyl-homoserine lactones (AHLs) as autoinducers of Gram-negative bacteria for quorum sensing regulation have shown positive effects on the production of aromatic proteins in extracellular polymeric substances (EPSs) during bioflocculation. To investigate the role of AHLs in aromatic protein production, a Chlorella-bacteria system with great bioflocculation was established via fed-batch cultivation. Tryptophan and aromatic proteins as the main compounds in the EPS of bioflocs showed an increasing trend during fed-batch cultivation. The Chlorella cells only secreted tryptophan rather than aromatic proteins during axenic cultivation. N-dodecanoyl-L-Homoserine lactone (C12-HSL) was correlated with the flocculation activity and extracellular protein content of bioflocs during fed-batch cultivation. The addition of exogenous C12-HSL enhanced the flocculation activity of the Chlorella-bacteria system and aromatic protein production in the EPS. Chlorella cells sensed exogenous C12-HSL and significantly upregulated the aromatic protein synthesis pathway during axenic cultivation. In addition, vanillin as a quorum-sensing inhibitor suppressed the positive effect of C12-HSL on flocculation activity and aromatic protein production and synthesis. This result indicated that vanillin intercepts the response of Chlorella cells to C12-HSL. Overall, C12-HSL is supposed to be an important signal molecule to achieve communication between Chlorella and Gram-negative bacteria and subsequently induce Chlorella cells to produce aromatic proteins for biofloc formation.
Production of N-acyl homoserine lactones by Chromobacterium haemolyticum KM2 isolated from the river water in Malaysia
Arch Microbiol 2018 Sep;200(7):1135-1142.PMID:29796703DOI:10.1007/s00203-018-1526-y.
Quorum sensing (QS) is a term used to describe cell-to-cell communication that enables bacteria to orchestrate group behaviours according to density of bacterial cells. In Gram-negative bacteria, this signalling system is widely known to regulate a variety of different phenotypes such as antibiotic production and biofilm formation. In this study, we report the production of N-acyl homoserine lactones produced by Chromobacterium haemolyticum strain KM2, a bacterium isolated from a river water of a reserved tropical national park. Preliminary screening of QS activity using biosensor reporter assays indicated that C. haemolyticum strain KM2 produces both short- and long-chain AHLs. Analysis with high-resolution liquid chromatography-mass spectrometry (LC-MS/MS) analysis revealed the production of three AHLs by strain KM2: N-octanoyl-L-homoserine lactone (C8-HSL), N-dodecanoyl-L-Homoserine lactone (C12-HSL), and N-3-oxo-dodecanoyl-L-homoserine lactone (OC12-HSL). This bacterial isolate also exhibited strong β-haemolytic activity. To the best of our knowledge, this is the first documentation of QS activity and multiple AHLs production by C. haemolyticum strain KM2.
Characterization of quorum sensing and quorum quenching soil bacteria isolated from Malaysian tropical montane forest
Sensors (Basel) 2012;12(4):4846-59.PMID:22666062DOI:10.3390/s120404846.
We report the production and degradation of quorum sensing N-acyl-homoserine lactones by bacteria isolated from Malaysian montane forest soil. Phylogenetic analysis indicated that these isolates clustered closely to the genera of Arthrobacter, Bacillus and Pseudomonas. Quorum quenching activity was detected in six isolates of these three genera by using a series of bioassays and rapid resolution liquid chromatography analysis. Biosensor screening and high resolution liquid chromatography-mass spectrometry analysis revealed the production of N-dodecanoyl-L-Homoserine lactone (C12-HSL) by Pseudomonas frederiksbergensis (isolate BT9). In addition to degradation of a wide range of N-acyl-homoserine lactones, Arthrobacter and Pseudomonas spp. also degraded p-coumaroyl-homoserine lactone. To the best of our knowledge, this is the first documentation of Arthrobacter and Pseudomonas spp. capable of degrading p-coumaroyl-homoserine lactone and the production of C12-HSL by P. frederiksbergensis.
Transboundary intercellular communications between Penicillium and bacterial communities during sludge bulking: Inspirations on quenching fungal dominance
Water Res 2022 Aug 1;221:118829.PMID:35839592DOI:10.1016/j.watres.2022.118829.
Fungal bulking is caused by the evolution toward a fungi-dominant unbalanced sludge system, which is indeed the phenomenon of fungi competing against bacterial cells. We hypothesized that the cross-kingdom intercellular communication between fungi and bacteria was internal driving force that stimulated fungal bulking. In this study, we identified three signal molecules related to Penicillium fungi bulking under low-pH stress in an activated sludge reactor, which inspired us to propose a sludge bulking prevention strategy using the quorum quenching theory. When pH dropped from 7.0 to 4.5, the abundance of Penicillium increased from 12.5% to 44.8%. However, some functional bacterial genera, such as Nitrosomonas and Sphingopyxis, were washed out from the sludge. The production of quorum-sensing (QS) molecules N-Heptanoyl-L-homoserine lactone (C7-HSL), N-dodecanoyl-L-Homoserine lactone (C12-HSL), and N-Tetradecanoyl-L-homoserine lactone (C14-HSL) was regulated with sludge bulking; especially the response of the latter two was significantly negative to Penicillium blooming (P < 0.05). To test their roles, trace commercial C12-HSL and C14-HSL were added to Penicillium culture, successfully causing 8.3% and 30.2% inhibition of mycelial formation, respectively. They also contributed to the improvement of activated sludge settleability by 6.1% and 39.7%, respectively (represented by sludge volume index). The transcriptome technique further revealed the regulation of the expression of genes in |logFC| >1, involving signal transduction, mycelium synthesis, and metabolic pathways. Our study provided an innovative strategy for controlling fungal bulking from the perspective of microbial transboundary informatics.