N-heptanoyl-L-Homoserine lactone
(Synonyms: C7-HSL) 目录号 : GC44395A bacterial quorum sensing signal molecule
Cas No.:177158-20-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- 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 involved in a promising field of study. 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-heptanoyl-L-Homoserine lactone (C7-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism. [1] [2] The diverse applications of this molecule include regulation of virulence, infection prevention, and septicemia in fish. [3]
Reference:
[1]. 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).
[2]. Barnard, A.M.L., and Salmond, G.P.C. Quorum sensing: The complexities of chemical communication between bacteria. Complexus 5(2), 87-101 (2004).
[3]. Morohoshi, T., Inaba, T., Kato, N., et al. Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen edwardsiella tarda. Journal of Bioscience and Bioengineering 98(4), 274-281 (2004).
| Cas No. | 177158-20-2 | SDF | |
| 别名 | C7-HSL | ||
| 化学名 | N-[(3S)-tetrahydro-2-oxo-3-furanyl]-heptanamide | ||
| Canonical SMILES | CCCCCCC(=O)N[C@H]1CCOC1=O | ||
| 分子式 | C11H19NO3 | 分子量 | 213.3 |
| 溶解度 | 30 mg/ml in DMSO, 30 mg/ml in DMF, 20 mg/ml in Ethanol | 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 | 4.6882 mL | 23.4412 mL | 46.8823 mL |
| 5 mM | 0.9376 mL | 4.6882 mL | 9.3765 mL |
| 10 mM | 0.4688 mL | 2.3441 mL | 4.6882 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 presence and role of bacterial quorum sensing in activated sludge
Microb Biotechnol 2012 Sep;5(5):621-33.PMID:22583685DOI:10.1111/j.1751-7915.2012.00348.x.
Activated sludge used for wastewater treatment globally is composed of a high-density microbial community of great biotechnological significance. In this study the presence and purpose of quorum sensing via N-acylated-l-homoserine lactones (AHLs) in activated sludge was explored. The presence of N-heptanoyl-L-Homoserine lactone in organic extracts of sludge was demonstrated along with activation of a LuxR-based AHL monitor strain deployed in sludge, indicating AHL-mediated gene expression is active in sludge flocculates but not in the bulk aqueous phase. Bacterial isolates from activated sludge were screened for AHL production and expression of phenotypes commonly but not exclusively regulated by AHL-mediated gene transcription. N-acylated-l-homoserine lactone and exoenzyme production were frequently observed among the isolates. N-acylated-l-homoserine lactone addition to sludge upregulated chitinase activity and an AHL- and chitinase-producing isolate closely related to Aeromonas hydrophila was shown to respond to AHL addition with upregulation of chitinase activity. N-acylated-l-homoserine lactones produced by this strain were identified and genes ahyI/R and chiA, encoding AHL production and response and chitinase activity respectively, were sequenced. These experiments provide insight into the relationship between AHL-mediated gene expression and exoenzyme activity in activated sludge and may ultimately create opportunities to improve sludge performance.
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.
Structural and Biochemical Characterization of AidC, a Quorum-Quenching Lactonase with Atypical Selectivity
Biochemistry 2015 Jul 21;54(28):4342-53.PMID:26115006DOI:10.1021/acs.biochem.5b00499.
Quorum-quenching catalysts are of interest for potential application as biochemical tools for interrogating interbacterial communication pathways, as antibiofouling agents, and as anti-infective agents in plants and animals. Herein, the structure and function of AidC, an N-acyl-l-homoserine lactone (AHL) lactonase from Chryseobacterium, is characterized. Steady-state kinetics show that zinc-supplemented AidC is the most efficient wild-type quorum-quenching enzymes characterized to date, with a kcat/KM value of approximately 2 × 10(6) M(-1) s(-1) for N-heptanoyl-L-Homoserine lactone. The enzyme has stricter substrate selectivity and significantly lower KM values (ca. 50 μM for preferred substrates) compared to those of typical AHL lactonases (ca. >1 mM). X-ray crystal structures of AidC alone and with the product N-hexanoyl-l-homoserine were determined at resolutions of 1.09 and 1.67 Å, respectively. Each structure displays as a dimer, and dimeric oligiomerization was also observed in solution by size-exclusion chromatography coupled with multiangle light scattering. The structures reveal two atypical features as compared to previously characterized AHL lactonases: a "kinked" α-helix that forms part of a closed binding pocket that provides affinity and enforces selectivity for AHL substrates and an active-site His substitution that is usually found in a homologous family of phosphodiesterases. Implications for the catalytic mechanism of AHL lactonases are discussed.
The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci
Mol Microbiol 2000 Jul;37(1):81-97.PMID:10931307DOI:10.1046/j.1365-2958.2000.01960.x.
N-(3-hydroxy-7-cis-tetradecenoyl)-L-homoserine lactone (3OH, C14:1-HSL) is a quorum-sensing signalling molecule produced by Rhizobium leguminosarum. It is unusual in that it inhibits the growth of several strains of R. leguminosarum and was previously known as 'small bacteriocin'. The cinRI locus responsible for the production of 3OH,C14:1-HSL has been characterized; it is predicted to be on the chromosome, based on DNA hybridization. The cinR and cinI genes are in different transcriptional units, separated by a predicted transcription terminator. CinR regulates cinI expression to a very high level in a cell-density dependent manner, and cinI expression is positively autoregulated by 3OH,C14:1-HSL, the only identified N-acyl homoserine lactone (AHL) produced by CinI. No other AHLs were identified that strongly induced cinI expression. Mutation of cinI or cinR abolishes the production of 3OH,C14:1-HSL and also reduces the production of several other AHLs. This is thought to result from the expression of three other AHL production loci being affected by the absence of 3OH,C14:1-HSL. AHLs produced by these other loci include N-hexanoyl- and N-octanoyl-L-homoserine lactones and, unexpectedly, N-heptanoyl-L-Homoserine lactone (C7-HSL). The expression of the rhiI gene on the symbiotic plasmid is greatly reduced in a cinI mutant, and the major regulatory effect appears to be mediated at least in part as a result of an effect on expression of RhiR, the regulator of rhiI. Thus, cinR and cinI appear to be at the top of a regulatory cascade or network that influences several AHL-regulated quorum-sensing loci. The expression of cinI-lacZ fusions is significantly reduced (but not abolished) when the symbiosis plasmid pRL1JI is present, resulting in a reduction in the level of 3OH,C14:1-HSL produced. Mutation of cinI had little effect on growth or nodulation. However, plasmid transfer was affected, and the results obtained indicate that 3OH,C14:1-HSL produced by either the donor or the recipient in mating experiments can stimulate transfer of pRL1JI.
[Influences of abaR gene on biofilm formation of Acinetobacter baumannii]
Zhonghua Shao Shang Za Zhi 2017 Apr 20;33(4):200-205.PMID:28427132DOI:10.3760/cma.j.issn.1009-2587.2017.04.003.
Objective: To detect drug-resistant phenotype and abaR gene of Acinetobacter baumannii (AB) and investigate influences of abaR gene on biofilm formation of AB. Methods: From February to July 2014, 159 strains AB were collected from Department of Clinical Microbiology of Ruijin Hospital of School of Medicine of Shanghai JiaoTong University and numbered starting from 1 according time when they were collected. (1) The above-mentioned 159 strains of AB were identified by detecting gene sequence of 16S ribosomal DNA. According to results of drug sensitivity test, extensively drug-resistant strains and sensitive strains of AB were selected and counted, and their sources were recorded. (2) Extensively drug-resistant strains and sensitive strains of AB were collected to measure biofilm formation (denoted as absorbance value) by methyl thiazolyl tetrazolium method when strains at culture hour 12, 24, 48 and 72. (3) The abaR gene sequence of ATCC 17978 of AB was analyzed through Gene banks of National Center for Biotechnology Information and compared with AqsR gene sequence of LuxR type receptor of Acinetobacter oleivorans DR1. No. 87 and No. 96 AB strains were amplified and sequenced by polymerase chain reaction according to target gene sequence of abaR of ATCC 17978 of AB. The sequencing result was compared with abaR gene sequence of ATCC 17978. (4) No. 87 and No. 96 AB strains were collected and divided into 0.1% dimethyl sulfoxide (DMSO) group, 10 μmol/L N-heptanoyl-L-Homoserine lactone (C7-HSL) group, 10 μmol/L N-(3-Hydroxydodecanoyl)-DL-homoserine lactone (OH-dDHL) group, 1% DMSO group, 100 μmol/L C7-HSL group, and 100 μmol/L OH-dDHL, with 3 wells of each group. AB strains in the above groups were respectively dealt with DMSO of corresponding final volume fraction, C7-HSL and OH-dDHL of corresponding final amount-of-substance concentration. Biofilm formation (denoted as absorbance value) of AB was measured by methyl thiazolyl tetrazolium method at culture hour 12, 24, 48 and 72. Data were processed with analysis of variance of factorial design, one-way analysis of variance, LSD test and Bonferroni correction. Results: (1) There were 18 extensively drug-resistant strains and 5 sensitive strains of AB. Samples of extensively drug-resistant strains were mainly collected from Emergency ICU and Department of Burns and Plastic Surgery of our hospital and were mainly from sputum, blood, and wound exudate. Samples of sensitive strains were collected dispersedly and were mainly from sputum. (2) Absorbance values of extensively drug-resistant strains and sensitive strains of AB at all culture time points were similar (with P values above 0.05). Absorbance value of extensively drug-resistant strains of AB at culture hour 24 was obviously higher than that of these strains at culture hour 12, 48, or 72 (with P values below 0.01). Absorbance value of sensitive strains of AB at culture hour 24 was obviously higher than that of these strains at culture hour 12 (P<0.01). (3) AbaR gene sequence of LuxR type receptor existed in AB. Similarity ratio between abaR gene sequence and LuxR type receptor AqsR gene sequence in Acinetobacter oleivorans DR1 was 87%. Similarity ratios between abaR gene sequence of No. 87 and No. 96 strains and ATCC 17978 of AB were 98% and 99%, respectively. (4) Absorbance values of 0.1% DMSO group of No. 87 strain at all culture time points were similar to those of 1% DMSO group (with P values above 0.05). Absorbance value of 0.1% DMSO group of No. 96 strain at culture hour 12 was obviously lower than that of 1% DMSO group (P<0.01), while that at culture hour 24 was obviously lower than that of 1% DMSO group (P<0.01). Absorbance values of 10 μmol/L C7-HSL group of No. 87 and No. 96 strains at culture hour 24 were obviously lower than those of 0.1% DMSO group (with P values below 0.01). Absorbance values of 100 μmol/L C7-HSL group of No. 87 strain at all culture time points were similar to those of 1% DMSO group, respectively (with P values above 0.05). Absorbance value of 100 μmol/L C7-HSL group of No. 96 strain at culture hour 12 was lower than that of 1% DMSO group (P<0.01). Absorbance values of 10 μmol/L OH-dDHL group of No. 87 and No. 96 strains were similar to those of 0.1% DMSO group (with P values above 0.05). Absorbance values of 100 μmol/L OH-dDHL group of No. 87 strain at all culture time points were similar to those of 1% DMSO group (with P values above 0.05). Absorbance value of 100 μmol/L OH-dDHL group of No. 96 strain at culture hour 12 was obviously higher than that of 1% DMSO group (P<0.01). Absorbance values of 0.1% DMSO group and 1% DMSO group of No. 87 and No. 96 strains at culture hour 24 were obviously higher than those at culture hour 12 and 48 (with P values below 0.01). Conclusions: Extensively drug-resistant strains of AB exist commonly. AbaR gene exists in AB has relation with biofilm formation of AB.