Anandamide
(Synonyms: 花生四烯酸乙醇胺) 目录号 : GC35339
Anandamide是一种来源于含花生四烯酸膜脂的内源性大麻素,通过结合并激活CB1和CB2大麻素受体以及香草素瞬时受体电位通道1(TRPV1)受体发挥作用。
Cas No.:94421-68-8
Sample solution is provided at 25 µL, 10mM.
Anandamide, an endocannabinoid derived from arachidonic acid-containing membrane lipids, exerts its actions by binding and activating CB1 and CB2 receptors (cannabinoid receptors 1 and 2) and the vanilloid transient receptor potential vanilloid 1 (TRPV1) receptor[1-2]. Anandamide is involved in the regulation of pain, mood, and cognition[3].
In vitro, primary microglial cultures were pretreated with 1μM Anandamide for 30min, stimulated with 100ng/mL Lipopolysaccharide (LPS) for 24h, and assayed for nitric oxide; LPS alone markedly increased nitric oxide (NO) release, whereas Anandamide reduced it by ~30%[4]. Pretreating human vascular smooth muscle cells (hVSMC) with 100nM Anandamide for 1h (protein assays) or 2.5h (immunofluorescence and PLA) suppressed the cytokine-induced expression of 21 inflammatory genes, including the key chemokine CCL2, by elevating H3K27me3 and reducing H3K27ac at the CCL2 promoter, thereby compacting chromatin[5].
In vivo, after intraperitoneal administration of Anandamide (10mg/kg) to mice, hyperglycemia after oral glucose loading was improved, whereas glucose clearance and insulin sensitivity were impaired, without altering transporter-mediated glucose absorption[6]. Following two bilateral intracerebroventricular injections (2μL; 1μL/min; 100ng) of Anandamide to male Wistar rats, Anandamide prevented streptozotocin (STZ)-induced deficits in recognition and non-associative emotional memory without affecting tone fear conditioning, blocked STZ-elicited enlargement of the cerebral ventricles, and, like STZ, decreased Bcl2-associated athanogene (BAG2) levels[7].
References:
[1] Goodfellow CE, Glass M. Anandamide receptor signal transduction. Vitam Horm. 2009;81:79-110.
[2] Biringer RG. The rise and fall of anandamide: processes that control synthesis, degradation, and storage. Mol Cell Biochem. 2021;476(7):2753-2775.
[3] Leweke FM, Piomelli D, Pahlisch F, et al. Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia. Transl Psychiatry. 2012;2(3):e94. Published 2012 Mar 20.
[4] Malek N, Popiolek-Barczyk K, Mika J, et al. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast. 2015;2015:130639.
[5] Pflüger-Müller B, Oo JA, Heering J, et al. The endocannabinoid anandamide has an anti-inflammatory effect on CCL2 expression in vascular smooth muscle cells. Basic Res Cardiol. 2020;115(3):34.
[6] Troy-Fioramonti S, Demizieux L, Gresti J, et al. Acute activation of cannabinoid receptors by anandamide reduces gastrointestinal motility and improves postprandial glycemia in mice. Diabetes. 2015;64(3):808-818.
[7] Moreira-Silva D, Carrettiero DC, Oliveira ASA, et al. Anandamide Effects in a Streptozotocin-Induced Alzheimer's Disease-Like Sporadic Dementia in Rats. Front Neurosci. 2018;12:653.
Anandamide是一种来源于含花生四烯酸膜脂的内源性大麻素,通过结合并激活CB1和CB2大麻素受体以及香草素瞬时受体电位通道1(TRPV1)受体发挥作用[1-2]。Anandamide参与疼痛、情绪和认知的调节[3]。
在体外,原代小胶质细胞经1μM的Anandamide预处理30分钟后,再以100ng/mL脂多糖(LPS)刺激24小时,结果显示LPS显著增加一氧化氮(NO)释放,而Anandamide可将其降低约30%[4]。用100nM的Anandamide预处理人血管平滑肌细胞(hVSMC)1小时(用于蛋白检测)或2.5小时(用于免疫荧光和PLA),可通过在CCL2启动子区域升高H3K27me3并降低H3K27ac,使染色质紧缩,抑制细胞因子诱导的21种炎症基因(包括关键趋化因子CCL2)的表达[5]。
在体内,小鼠腹腔注射Anandamide(10mg/kg)后,口服葡萄糖负荷引起的高血糖得到改善,但葡萄糖清除率和胰岛素敏感性受损,且未改变转运介导的葡萄糖吸收[6]。对雄性Wistar大鼠进行两次双侧脑室注射Anandamide(2μL; 1μL/min; 100ng),可预防链脲佐菌素(STZ)诱导的认知和非联想性情绪记忆障碍,且不影响音调恐惧条件反射;同时可阻断STZ引起的脑室扩大,并与STZ一样降低Bcl2相关抗凋亡蛋白(BAG2)水平[7]。
Cell experiment [1]: | |
Cell lines | Primary microglial cell |
Preparation Method | Adherent cells were incubated for 48h in culture medium before being used for the analyses. Primary microglial cell cultures were treated with 1μM Anandamide for 30min and then for 24h with Lipopolysaccharide (LPS) (100ng/mL) for mRNA analysis. |
Reaction Conditions | 1μM; 30min |
Applications | An increase in the secretion of nitric oxide (NO) was observed 24h after the administration of LPS (100ng/mL). Anandamide (1μM) administered 30min prior to LPS stimulation reduced NO production by approximately 30%. |
Animal experiment [2]: | |
Animal models | Male Wistar rats |
Preparation Method | Each animal received two intracerebroventricular (icv) bilateral injections of 2μL (1μL/min): the first one was citrate (vehicle) or Anandamide (100ng), followed by another injection of vehicle or streptozotocin (STZ) (2mg/kg) 5min later. After each infusion, the injection needle remained for at least 2min in place, to prevent reflux of the administered solution. After surgery, animals received intramuscular injections of an antibiotic and an anti-inflammatory, and an analgesic. Also, 2mL of saline solution was administered subcutaneously for rehydration, and the animals were maintained in thermal blankets with controlled temperature until recovery. Animals were kept in individual home cages for 5 days after surgery, and body weight, food, water intake, and animal well-being were accompanied daily. |
Dosage form | 2μL; 1μL/min; 100ng; intracerebroventricular (icv) bilateral injections |
Applications | Anandamide prevented recognition and non-associative emotional memory impairments induced by STZ, but did not influence tone fear conditioning. STZ increased the brain ventricular area, and this enlargement was prevented by Anandamide. Bcl2-associated athanogene (BAG2) levels were decreased by STZ and Anandamide. |
References: |
Cas No. | 94421-68-8 | SDF | |
别名 | 花生四烯酸乙醇胺 | ||
化学名 | N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide | ||
Canonical SMILES | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCO)=O | ||
分子式 | C22H37NO2 | 分子量 | 347.53 |
溶解度 | 30mg/mL in DMSO, or 10mg/mL in DMF | 储存条件 | Store at -20°C,stored under nitrogen |
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1 mg | 5 mg | 10 mg |
1 mM | 2.8774 mL | 14.3872 mL | 28.7745 mL |
5 mM | 0.5755 mL | 2.8774 mL | 5.7549 mL |
10 mM | 0.2877 mL | 1.4387 mL | 2.8774 mL |
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