N-hexanoyl-L-Homoserine lactone3X 积分

目录号: GC41398纯度: >95.00%同义词: 己酰-L-高丝氨酸内酯,C6-HSL
N-hexanoyl-L-Homoserine lactone是一种短链N-酰基高丝氨酸内酯(AHL),在微生物细胞间通讯系统中扮演着重要角色。

N-hexanoyl-L-Homoserine lactone
Cas No.: 147852-83-3
规格价格库存数量操作
5mg¥325.00现货
1
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50mg¥1,794.00现货
1

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产品描述 Description

N-hexanoyl-L-Homoserine lactone is a short-chain N-acyl homoserine lactone (AHL) which plays important roles in cell–cell communication system among microorganisms. N-hexanoyl-L-Homoserine lactone consists of a homoserine lactone ring linked via an amide bond to a six-carbon saturated acyl chain (hexanoyl). At neutral pH and room temperature, N-hexanoyl-L-Homoserine lactone is a water-soluble and lipophilic signal that diffuses freely across bacterial membranes, allowing rapid population-wide signal distribution[1][2].

In vitro, different amounts of N-hexanoyl-L-Homoserine lactone (0.001µg/ml, 1µg/ml, and 100µg/ml) were added to the culture medium of Escherichia coli and then incubated at 35 ± 2ºC for 16 to 20h in an ambient air incubator. With increasing of N-hexanoyl-L-Homoserine lactone concentration, an increase in dry cell weight (2.45mg/ml to 4.63mg/ml) and insulin like growth factor 1(IGF-I) expression level (0.4mg/ml to 0.77mg/ml) was observed. N-hexanoyl-L-Homoserine lactone can be considered as protein production inducer in bacterial expression systems through the quorum sensing pathways[3]. The experimental strain LB-001 was cultured in LB medium under conditions of 30℃, 10℃, and 10℃ with 2μM N-hexanoyl-L-Homoserine lactone added every 24h for up to 96h. N-hexanoyl-L-Homoserine lactone enhances the cold resistance of strain LB-001 by upregulating energy metabolism, antioxidation, and fatty acid synthesis genes, increasing ATP, superoxide dismutase (SOD), and reducing reactive oxygen species (ROS) levels under low-temperature stress[3]. Winter-wheat seeds were primed in a 100ng/mL solution of N-hexanoyl-L-Homoserine lactone for 3h before the germination and seedling development were tested. Priming had a significant positive effect on germination with levels 1.2-fold greater than the untreated controls and increased coleoptile and radicle lengths 1.4-fold within two days. N-hexanoyl-L-Homoserine lactone may be a viable phyto-stimulator when applied as a seed primer[4].

References:
[1] Stock F, Bilcke G, Decker S D, et al. Distinctive Growth and Transcriptional Changes of the Diatom Seminavis robusta in Response to Quorum Sensing Related Compounds. Front Microbiol. 2020 Jun 9:11:1240.
[2] Zhang, Y., Liu, F., Li, J.,et al. Specific quorum sensing signal molecules inducing the social behaviors of microbial populations in anaerobic digestion. Bioresource Technology. 2019 Feb; 273, 185–195.
[3] Babaeipour V, Vahidi H, Alikhani S, et al. Effect of Acyl Homoserine Lactone on Recombinant Production of Human Insulin-like Growth Factor-1 in Batch Culture of Escherichia coli. Protein Pept Lett. 2018;25(11):980-985.
[4] Wang Y B, Gu J M, Zhang F L,et al. Multi-omics analysis reveals the mechanisms by which C6-HSL enhances the resistance of typical functional bacteria in activated sludge to low-temperature stress. Sci Total Environ. 2024 Dec 1:954:176454.
[5] Moshynets O V, Babenko L M, Rogalsky S P, et al. Priming winter wheat seeds with the bacterial quorum sensing signal N-hexanoyl-L-Homoserine lactone (C6-HSL) shows potential to improve plant growth and seed yield. PLoS One. 2019 Feb 25;14(2):e0209460.

N-hexanoyl-L-Homoserine lactone是一种短链N-酰基高丝氨酸内酯(AHL),在微生物细胞间通讯系统中扮演着重要角色。N-hexanoyl-L-Homoserine lactone由一个高丝氨酸内酯环通过酰胺键连接一条六碳饱和酰基链(己酰基)构成。在中性pH和室温下,N-hexanoyl-L-Homoserine lactone是水溶且亲脂的信号分子,可自由扩散穿过细菌膜,实现快速的群体信号传播[1][2]

体外实验中,将不同浓度的N-hexanoyl-L-Homoserine lactone(0.001µg/ml、1µg/ml和100µg/ml)加入大肠杆菌培养基,于35±2ºC环境空气培养箱中孵育16–20h。随着N-hexanoyl-L-Homoserine lactone浓度升高,细胞净重由2.45mg/ml增至4.63mg/ml,类胰岛素生长因子1(IGF-I)表达水平由0.4mg/ml升至0.77mg/ml。因此,N-hexanoyl-L-Homoserine lactone可通过群体感应途径作为细菌表达系统中的蛋白产量诱导剂[3]。菌株LB-001在30℃、10℃和10℃条件下于LB培养基中培养,每24h添加2μM的N-hexanoyl-L-Homoserine lactone,持续96h。N-hexanoyl-L-Homoserine lactone通过上调能量代谢、抗氧化和脂肪酸合成基因,提高ATP和超氧化物歧化酶(SOD)水平,降低低温胁迫下的活性氧(ROS)水平,从而增强LB-001的耐寒性[3]。冬小麦种子在100ng/mL的N-hexanoyl-L-Homoserine lactone溶液中浸种3h后进行发芽和幼苗测试。与未处理对照相比,浸种使发芽率提高1.2倍,两天内胚芽鞘和胚根长度增加1.4倍。N-hexanoyl-L-Homoserine lactone作为种子引发剂具有成为可行植物刺激剂的潜力[4]

实验参考方法 Experimental Reference Method

Cell experiment [1]:

Cell lines

LB-001 bacteria

Preparation Method

The experimental strain LB-001 was cultured in LB medium under conditions of 30℃, 10℃, and 10℃ with 2μM N-hexanoyl-L-Homoserine lactone added every 24h. During biochemical analysis, samples were taken at 2, 4, 6, 8, 10, 12, 24, 36, 48, 60, 72, 84 and 96h.

Reaction Conditions

2μM; 96h

Applications

N-hexanoyl-L-Homoserine lactone increases ATP concentration and SOD, POD and GSH-Px activity in strain LB-001 while reducing ROS levels and repairing cold-induced cell membrane damage.

References:
[1] Wang Y B, Gu J M, Zhang F L,et al. Multi-omics analysis reveals the mechanisms by which C6-HSL enhances the resistance of typical functional bacteria in activated sludge to low-temperature stress. Sci Total Environ. 2024 Dec 1:954:176454.

产品文档 Product Documents

Purity:>95.00%Appearance:A solid

化学性质Chemical Properties

CAS 号
147852-83-3
同义词
己酰-L-高丝氨酸内酯,C6-HSL
SMILES
CCCCCC(=O)N[C@H]1CCOC1=O
分子式
C10H17NO3
分子量
199.2 g/mol
溶解性
DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml
保存条件
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°C,然后在超声波浴中震荡一段时间。
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。

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