N-hexanoyl-L-Homoserine lactone
(Synonyms: 己酰-L-高丝氨酸内酯,C6-HSL) 目录号 : GC41398
A bacterial quorum sensing signal molecule
Cas No.:147852-83-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- 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. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-hexanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism. The diverse applications of this molecule include regulation of virulence in general and in cystic fibrosis, infection prevention, slime and biofilm reduction in commercial agriculture and aquaculture industries, food spoilage prevention, and septicemia in fish.
| Cas No. | 147852-83-3 | SDF | |
| 别名 | 己酰-L-高丝氨酸内酯,C6-HSL | ||
| Canonical SMILES | CCCCCC(=O)N[C@H]1CCOC1=O | ||
| 分子式 | C10H17NO3 | 分子量 | 199.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml | 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 | 5.0201 mL | 25.1004 mL | 50.2008 mL |
| 5 mM | 1.004 mL | 5.0201 mL | 10.0402 mL |
| 10 mM | 0.502 mL | 2.51 mL | 5.0201 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。
Exogenous N-hexanoyl-L-Homoserine lactone assists in upflow anaerobic sludge blanket recovery from acetate accumulation via aceticlastic methanogens enrichment
Bioresour Technol 2022 Feb;346:126600.PMID:34973403DOI:10.1016/j.biortech.2021.126600.
Volatile fatty acids (VFAs) accumulation caused by shock loading severely hampers the performance and stability of anaerobic digestion. An upflow anaerobic sludge blanket (UASB) was operated to examine its performance, sludge properties, and microbial community behavior during shock loading and recovery with exogenous N-hexanoyl-L-Homoserine lactone (C6-HSL). After shock loading, chemical oxygen demand (COD) removal was significantly reduced from 79.09% to 65.63%. The abundance of Methanosarcinales also significantly decreased, which resulted in acetate accumulation (1,163.55 mg/L). Sludge granules disintegrated along with the decrease in extracellular polymeric substances (EPS). After supplying 1 μg/L C6-HSL, COD removal resumed to 75.10%. Furthermore, C6-HSL enhanced the abundance and metabolic activity of aceticlastic methanogens, decreased acetate concentration to 146.87 mg/L, improved EPS secretion, and caused the re-assembly of disintegrated sludges to form large granules. These results advanced our understanding of microbial community behavior and provided an attractive strategy for restoration of UASB recovered from shock loading.
Effect of the N-hexanoyl-L-Homoserine lactone on the Carbon Fixation Capacity of the Algae-Bacteria System
Int J Environ Res Public Health 2023 Mar 13;20(6):5047.PMID:36981956DOI:10.3390/ijerph20065047.
Algae-bacteria systems are used widely in wastewater treatment. N-hexanoyl-L-Homoserine lactone (AHL) plays an important role in algal-bacteria communication. However, little study has been conducted on the ability of AHLs to regulate algal metabolism and the carbon fixation ability, especially in algae-bacteria system. In this study, we used the Microcystis aeruginosa + Staphylococcus ureilyticus strain as a algae-bacteria system. The results showed that 10 ng/L C6-HSL effectively increased the chlorophyll-a (Chl-a) concentration and carbon fixation enzyme activities in the algae-bacteria group and algae group, in which Chl-a, carbonic anhydrase activity, and Rubisco enzyme increased by 40% and 21%, 56.4% and 137.65%, and 66.6% and 10.2%, respectively, in the algae-bacteria group and algae group, respectively. The carbon dioxide concentration mechanism (CCM) model showed that C6-HSL increased the carbon fixation rate of the algae-bacteria group by increasing the CO2 transport rate in the water and the intracellular CO2 concentration. Furthermore, the addition of C6-HSL promoted the synthesis and secretion of the organic matter of algae, which provided biogenic substances for bacteria in the system. This influenced the metabolic pathways and products of bacteria and finally fed back to the algae. This study provided a strategy to enhance the carbon fixation rate of algae-bacteria consortium based on quorum sensing.
N-hexanoyl-L-homoserine lactone-degrading Pseudomonas aeruginosa PsDAHP1 protects zebrafish against Vibrio parahaemolyticus infection
Fish Shellfish Immunol 2015 Jan;42(1):204-12.PMID:25449384DOI:10.1016/j.fsi.2014.10.033.
Four strains of N-hexanoyl-L-Homoserine lactone (AHL)-degrading Pseudomonas spp., named PsDAHP1, PsDAHP2, PsDAHP3, and PsDAHP4 were isolated and identified from the intestine of Fenneropenaeus indicus. PsDAHP1 showed the highest AHL-degrading activity among the four isolates. PsDAHP1 inhibited biofilm-forming exopolysaccharide and altered cell surface hydrophobicity of virulent green fluorescent protein (GFP)-tagged Vibrio parahaemolyticus DAHV2 (GFP-VpDAHV2). Oral administration of PsDAHP1 significantly reduced zebrafish mortality caused by GFP-VpDAHV2 challenge, and inhibited colonisation of GFP-VpDAHV2 in the gills and intestine of zebrafish as evidence by confocal laser scanning microscope and selective plating. Furthermore, zebrafish receiving PsDAHP1-containing feed had increased phagocytic cells of its leucocytes, increased serum activities of superoxide dismutase and lysozyme. The results suggest that Pseudomonas aeruginosa PsDAHP1 could protect zebrafish from V. parahaemolyticus infection by inhibiting biofilm formation and enhancing defence mechanisms of the fish.
Enhanced CO2 reduction and acetate synthesis in autotrophic biocathode by N-hexanoyl-L-Homoserine lactone (C6HSL)-based quorum-sensing regulation
Sci Total Environ 2022 Aug 25;836:155724.PMID:35523344DOI:10.1016/j.scitotenv.2022.155724.
The aim of this study was to investigate the ecological role of quorum-sensing signaling molecule on the autotrophic biocathode for CO2 reduction and acetate synthesis. As a typical quorum-sensing signaling molecule, N-hexanoyl-L-Homoserine lactone (C6HSL) was used to regulate the construction of cathode biofilm. Results showed that the maximum acetate production from CO2 reduction improved by 94.8%, and the maximum Faraday efficiency of the microbial electrosynthesis system enhanced by 71.7%, with the regulation of C6HSL. Electrochemical analyses indicated that higher electrochemical activity and lower charge resistance of biocathode were obtained with C6HSL than without C6HSL. Confocal laser scanning microscopy and electron inhibitor experiment suggested that exogenous C6HSL increased living biomass in the biofilm and facilitated the electron transfer pathway related to NADH dehydrogenase-CoQ and proton motive force. With the C6HSL regulation, the relative abundance of hydrogen producers (e.g., Desulfovibrio and Desulfomicrobium) increased, contributing to the improved performance of autotrophic biocathode.
Simultaneous quantitative profiling of N-acyl-L-homoserine lactone and 2-alkyl-4(1H)-quinolone families of quorum-sensing signaling molecules using LC-MS/MS
Anal Bioanal Chem 2011 Jan;399(2):839-50.PMID:21046079DOI:10.1007/s00216-010-4341-0.
An LC-MS/MS method, using positive mode electrospray ionization, for the simultaneous, quantitative and targeted profiling of the N-acyl-L-homoserine lactone (AHL) and 2-alkyl 4-(1H)-quinolone (AQ) families of bacterial quorum-sensing signaling molecules (QSSMs) is presented. This LC-MS/MS technique was applied to determine the relative molar ratios of AHLs and AQs produced by Pseudomonas aeruginosa and the consequences of mutating individual or multiple QSSM synthase genes (lasI, rhlI, pqsA) on AHL and AQ profiles and concentrations. The AHL profile of P. aeruginosa was dominated by N-butanoyl-L-homoserine lactone (C4-HSL) with lesser concentrations of N-hexanoyl-L-Homoserine lactone (C6-HSL) and 3-oxo-substituted longer chain AHLs including N-(3-oxodecanoyl)-L-homoserine lactone (3-oxo-C10-HSL) and N-(3-oxododecanoyl)-L-homoserine lactone (3-oxo-C12-HSL). The AQ profile of P. aeruginosa comprised the C7 and C9 long alkyl chain AQs including 2-heptyl-4-hydroxyquinoline (HHQ), 2-nonyl-4-hydroxyquinoline, the "pseudomonas quinolone signal" (2-heptyl-3-hydroxy-4-quinolone) and the N-oxides, 2-heptyl-4-hydroxyquinoline N-oxide and 2-nonyl-4-hydroxyquinoline N-oxide. Application of the method showed significant effects of growth medium type on the ratio and the nature of the QSSMs synthesized and the dramatic effect of single, double and triple mutations in the P. aeruginosa QS synthase genes. The LC-MS/MS methodology is applicable in organisms where either or both AHL and AQ QSSMs are produced and can provide comprehensive profiles and concentrations from a single sample.