N-dodecanoyl-L-Homoserine lactone
(Synonyms: 十二烷酰-L-高丝氨酸内酯,C12-HSL) 目录号 : GC44355
N-dodecanoyl-L-Homoserine lactone是一种参与群体感应（QS）的小型可扩散信号分子，能够控制基因表达并影响细菌的细胞代谢。
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.
N-dodecanoyl-L-Homoserine lactone是一种参与群体感应（QS）的小型可扩散信号分子，能够控制基因表达并影响细菌的细胞代谢 [1-2]。QS的中断被认为是降低细菌致病性和耐药性的一种刺激性方法 [3]。N-dodecanoyl-L-Homoserine lactone适配体可用于阻断铜绿假单胞菌（Pseudomonas aeruginosa）的QS并抑制其生物膜的形成 [4]。
在体外，N-dodecanoyl-L-Homoserine lactone（500nM; 2-5h）显著减少了极性生长期间半乳霉菌的孢子萌发数量和菌丝长度，并抑制了Ras1-cAMP-PKA信号转导和MAPK途径 [5]。N-dodecanoyl-L-Homoserine lactone（4, 8, 16, 32, 64, 128, 256, 512和1024µg/ml; 18h）对金黄色葡萄球菌具有抗菌作用，MIC90和MBC90分别为64和128μg/ml。N-dodecanoyl-L-Homoserine lactone（64和128μg/ml; 24, 48h）剂量与时间依赖性降低了CHO和HeLa细胞的细胞活力，Hela细胞和CHO细胞的IC50分别为256和512μg/ml [6]。
| 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 | |
| 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 | |||
 |
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 |
| 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。
Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet