N-dodecanoyl-L-Homoserine lactone

目录号: GC44355纯度: >99.00%同义词: 十二烷酰-L-高丝氨酸内酯,C12-HSL
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。

N-dodecanoyl-L-Homoserine lactone
Cas No.: 137173-46-7
规格价格库存数量操作
5mg¥350.00现货
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10mg¥560.00现货
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50mg¥1,960.00现货
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10mM (in 1mL DMSO)¥385.00现货
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产品描述 Description

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]

实验参考方法 Experimental Reference Method

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:
[1] 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.

产品文档 Product Documents

Purity:>99.00%

化学性质Chemical Properties

CAS 号
137173-46-7
同义词
十二烷酰-L-高丝氨酸内酯,C12-HSL
化学名
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
SMILES
CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
分子式
C16H29NO3
分子量
283.4 g/mol
溶解性
30mg/ml in DMSO, or in DMF
保存条件
Store at -20°C
General tips
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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。
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Shipping Condition
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