Linoleoyl Ethanolamide
(Synonyms: 亚油醇乙醇胺,LEA) 目录号 : GC44072An endocannabinoid
Cas No.:68171-52-8
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
Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain and murine peritoneal macrophages which contains linoleate in place of the arachidonate moiety of arachidonyl ethanolamide (AEA). [1] [2] It has weak affinity for the cannabinoid 1 (CB1) and CB2 receptors, exhibiting Ki values of 10 µM and 25 µM, respectively.[3] However, it is only approximately 4-fold less potent than AEA at causing catalepsy in mice (ED50 of 26.5 mg/kg). [4] In addition, linoleoyl ethanolamide increases ERK phosphorylation and AP-1-dependent transcription approximately 1.5 fold at 15 µM in a CB-receptor-independent manner.[5] However, cellular toxicity is readily apparent at concentrations of 10-20 µM. Linoleoyl ethanolamide inhibits human fatty acid amide hydrolase-dependent hydrolysis of AEA with a Ki value of 9.0 µM, but also is hydrolyzed effectively by the enzyme. [6][7]
Reference:
[1]. Patrono, C., Rotella, C.M., Toccafondi, R.S., et al. Prostacyclin stimulates the adenylate cyclase system of human thyroid tissue. Prostaglandins 22(1), 105-115 (1981).
[2]. Schmid, P.C., Kuwae, T., Krebsbach, R.J., et al. Anandanide and other N-acylethanolamines in mouse peritoneal macrophages. Chemistry and Physics of Lipids 87, 103-110 (1997).
[3]. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. Journal of Medicinal Chemistry 41, 5353-5361 (1998).
[4]. Watanabe, K., Matsunaga, T., Nakamura, S., et al. Pharmacological effects in mice of anandamide and its related fatty acid ethanolamides, and enhancement of cataleptogenic effect of anandamide by phenylmethylsulfonyl fluoride. Biological and Pharmaceutical Bullentin 22(4), 366-370 (1999).
[5]. Berdyshev, E.V., Schmid, P.C., Krebsbach, R.J., et al. Cannabinoid-receptor-independent cell signalling by N-acylethanolamines. Biochemistry Journal 360, 67-75 (2001).
[6]. Maccarrone, M., van der Stelt, M., Rossi, A., et al. Anandamide hydrolysis by human cells in culture and brain. The Journal of Biological Chemisty 273, 32332-32339 (1998).
[7]. Bisogno, T., Maurelli, S., Melck, D., et al. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. The Journal of Biological Chemisty 272, 3315-3323 (1997).
| Cas No. | 68171-52-8 | SDF | |
| 别名 | 亚油醇乙醇胺,LEA | ||
| 化学名 | N-(2-hydroxyethyl)-9Z,12Z-octadecadienamide | ||
| Canonical SMILES | CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO | ||
| 分子式 | C20H37NO2 | 分子量 | 323.5 |
| 溶解度 | 25 mg/ml in DMSO, 25 mg/ml in DMF, 50 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 | 3.0912 mL | 15.456 mL | 30.9119 mL |
| 5 mM | 0.6182 mL | 3.0912 mL | 6.1824 mL |
| 10 mM | 0.3091 mL | 1.5456 mL | 3.0912 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。
Synthesis of Linoleoyl Ethanolamide
J Oleo Sci 2013;62(6):427-33.PMID:23728334DOI:10.5650/jos.62.427.
Linoleoyl Ethanolamide has been showed to serve as a new and additional class of endogenous signaling molecule and exhibited a variety of biological activities in cells and tissues. Herein, we reported an effective method for the synthesis of Linoleoyl Ethanolamide. Enzymatic and chemical syntheses of Linoleoyl Ethanolamide were first compared and then reaction conditions were optimized. When the reaction was conducted at 30°C for 1 h by reacting 0.5 mmol methyl linoleate with 5 mmol ethanolamine in the presence of 15 μL, 5.4 mol/L sodium methoxide in methanol as catalyst, 97.2% Linoleoyl Ethanolamide was produced in the crude reaction mixture without further purification after the removal of excess ethanolamine. Additionally, the reaction can be conducted on a large scale, which resulted in the formation of 95.9% Linoleoyl Ethanolamide. Compared to previous studies, the amidation reaction between methyl linoleate and ethanolamine with sodium methoxide as catalyst for the synthesis of Linoleoyl Ethanolamide is more effective and faster. In addition, the reaction is scalable and reaction conditions are mild. This is the first time to use methyl linoleate to synthesize Linoleoyl Ethanolamide. Commercial Linoleoyl Ethanolamide is very expensive. However, the scalability and ease for such synthesis make it possible to study the biological and nutritional functions of the cannabinoid-like Linoleoyl Ethanolamide in animal or human subjects.
Adjunctive Probiotics Alleviates Asthmatic Symptoms via Modulating the Gut Microbiome and Serum Metabolome
Microbiol Spectr 2021 Oct 31;9(2):e0085921.PMID:34612663DOI:10.1128/Spectrum.00859-21.
Asthma is a multifactorial disorder, and microbial dysbiosis enhances lung inflammation and asthma-related symptoms. Probiotics have shown anti-inflammatory effects and could regulate the gut-lung axis. Thus, a 3-month randomized, double-blind, and placebo-controlled human trial was performed to investigate the adjunctive efficacy of probiotics in managing asthma. Fifty-five asthmatic patients were randomly assigned to a probiotic group (n = 29; received Bifidobacterium lactis Probio-M8 powder and Symbicort Turbuhaler) and a placebo group (n = 26; received placebo and Symbicort Turbuhaler), and all 55 subjects provided details of their clinical history and demographic data. However, only 31 patients donated a complete set of fecal and blood samples at all three time points for further analysis. Compared with those of the placebo group, co-administering Probio-M8 with Symbicort Turbuhaler significantly decreased the fractional exhaled nitric oxide level at day 30 (P = 0.049) and improved the asthma control test score at the end of the intervention (P = 0.023). More importantly, the level of alveolar nitric oxide concentration decreased significantly among the probiotic receivers at day 30 (P = 0.038), and the symptom relief effect was even more obvious at day 90 (P = 0.001). Probiotic co-administration increased the resilience of the gut microbiome, which was reflected by only minor fluctuations in the gut microbiome diversity (P > 0.05, probiotic receivers; P < 0.05, placebo receivers). Additionally, the probiotic receivers showed significantly changes in some species-level genome bins (SGBs), namely, increases in potentially beneficial species Bifidobacterium animalis, Bifidobacterium longum, and Prevotella sp. CAG and decreases in Parabacteroides distasonis and Clostridiales bacterium (P < 0.05). Compared with that of the placebo group, the gut metabolic potential of probiotic receivers exhibited increased levels of predicted microbial bioactive metabolites (Linoleoyl Ethanolamide, adrenergic acid, erythronic acid) and serum metabolites (5-dodecenoic acid, tryptophan, sphingomyelin) during/after intervention. Collectively, our results suggested that co-administering Probio-M8 synergized with conventional therapy to alleviate diseases associated with the gut-lung axis, like asthma, possibly via activating multiple anti-inflammatory pathways. IMPORTANCE The human gut microbiota has a potential effect on the pathogenesis of asthma and is closely related to the disease phenotype. Our trial has demonstrated that co-administering Probio-M8 synergized with conventional therapy to alleviate asthma symptoms. The findings of the present study provide new insights into the pathogenesis and treatment of asthma, mechanisms of novel therapeutic strategies, and application of probiotics-based therapy.
Linoleoyl Ethanolamide reduces lipopolysaccharide-induced inflammation in macrophages and ameliorates 2,4-dinitrofluorobenzene-induced contact dermatitis in mice
Eur J Pharmacol 2013 Jan 15;699(1-3):6-13.PMID:23201070DOI:10.1016/j.ejphar.2012.11.030.
In our previous study, it was found that Linoleoyl Ethanolamide (LE) is present in sake lees, which are produced as a byproduct during the making of Japanese sake. LE is a fatty acid ethanolamide, which have been demonstrated to exert a variety of biological functions, and in this study, the anti-inflammatory effects of LE were examined using in vitro cell culture and in vivo animal experiments. In mouse RAW264.7 macrophages, LE suppressed the lipopolysaccharide (LPS)-induced expression of pro-inflammatory cytokines, such as tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-6. In addition, LE inhibited LPS-induced increases in the levels of cyclooxygenase enzyme-2 and prostaglandin E(2), which are indicators of inflammation. The inhibitory effect of LE on the release of TNF-α was stronger than that of dipotassium glycyrrhizinate, which is widely used in external human skin care treatments. LE also suppressed the LPS-induced activation of Toll-like receptor 4 signaling and nuclear translocation of nuclear factor-κB (NF-κB) p65. In a contact dermatitis animal model, applying LE to affected ear skin ameliorated 2,4-dinitrofluorobenzene-induced contact dermatitis and pro-inflammatory cytokine expression at inflamed sites. These results indicate that LE exerts anti-inflammatory effects by inhibiting NF-κB signaling, and LE is proposed to be a useful therapeutic agent against contact dermatitis.
919 Syrup Alleviates Postpartum Depression by Modulating the Structure and Metabolism of Gut Microbes and Affecting the Function of the Hippocampal GABA/Glutamate System
Front Cell Infect Microbiol 2021 Aug 20;11:694443.PMID:34490139DOI:10.3389/fcimb.2021.694443.
Postpartum depression (PPD) is a mental disorder that affects pregnant women around the world, with serious consequences for mothers, families, and children. Its pathogenesis remains unclear, and medications for treating PPD that can be used during lactation remain to be identified. 919 syrup (919 TJ) is a Chinese herbal medicine that has been shown to be beneficial in the treatment of postpartum depression in both clinical and experimental studies. The mechanism of action of 919 TJ is unclear. 919 syrup is ingested orally, making the potential interaction between the drug and the gut microbiome impossible to ignore. We therefore hypothesized that 919 syrup could improve the symptoms of postpartum depression by affecting the structure and function of the intestinal flora, thereby altering hippocampal metabolism. We compared changes in hippocampal metabolism, fecal metabolism, and intestinal microflora of control BALB/c mice, mice with induced untreated PPD, and mice with induced PPD treated with 919 TJ, and found that 4-aminobutyric acid (GABA) in the hippocampus corresponded with PPD behaviors. Based on changes in GABA levels, multiple key gut bacterial species (Mucispirillum schaedleri, Bifidobacterium pseudolongum, Desulfovibrio piger, Alloprevotella tannerae, Bacteroides sp.2.1.33B and Prevotella sp. CAG:755) were associated with PPD. Metabolic markers that may represent the function of the intestinal microbiota in mice with PPD were identified (Met-Arg, urocanic acid, thioetheramide-PC, L-pipecolic acid, and Linoleoyl Ethanolamide). The relationship between these factors is not a simple one-to-one correspondence, but more likely a network of staggered functions. We therefore believe that the composition and function of the entire intestinal flora should be emphasized in research studying the gut and PPD, rather than changes in the abundance of individual bacterial species. The introduction of this concept of "GutBalance" may help clarify the relationship between gut bacteria and systemic disease.
Design and function of targeted endocannabinoid nanoparticles
Sci Rep 2022 Oct 14;12(1):17260.PMID:36241847DOI:10.1038/s41598-022-21715-1.
Nanoparticles and nano-delivery systems are constantly being refined and developed for biomedical applications such as imaging, gene therapy, and targeted delivery of drugs. Nanoparticles deliver beneficial effects by both release of their cargo and by liberation of their constitutive structural components. The N-acylethanolamines Linoleoyl Ethanolamide (LEA) and oleoyl ethanolamide (OEA) both exhibit endocannabinoid-like activity. Here, we report on their ability to form nanoparticles that when conjugated with tissue-specific molecules, are capable of localizing to specific areas of the body and reducing inflammation. The facilitation of pharmacological effects by endocannabinoids at targeted sites provides a novel biocompatible drug delivery system and a therapeutic approach to the treatment, patient management and quality of life, in conditions such as arthritis, epilepsy, and cancer.