[Leu5]-Enkephalin
(Synonyms: 亮氨酸脑啡肽,Leu-enkephalin; Leucine enkephalin; Leucyl-enkephalin) 目录号 : GC11236
[Leu5]-Enkephalin是一种通过与阿片受体结合以调节疼痛感知和情绪的内源性δ阿片受体激动剂。
![[Leu5]-Enkephalin Chemical Structure](/media/struct/GC1/GC11236.png "[Leu5]-Enkephalin Chemical Structure")
Cas No.:58822-25-6
Sample solution is provided at 25 µL, 10mM.
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[Leu5]-Enkephalin is an endogenous δ-opioid receptor agonist that modulates pain perception and emotion by binding to opioid receptors[1,2]. [Leu5]-Enkephalin is commonly used in the development of novel analgesic drugs and in the treatment and research of neurodegenerative diseases[3,4].
In vitro, [Leu5]-Enkephalin (5-50μM) treatment of human immortalized keratinocyte HaCaT cells for 21h significantly promoted cell migration and scratch wound closure. [Leu5]-Enkephalin (20μM) treatment of HaCaT cells for 24h significantly up-regulated the gene expression levels of matrix metalloproteinases MMP-2 and MMP-9[5]. [Leu5]-Enkephalin (50μg/mL) treatment of the scallop Chlamys farreri haemolymph for 1h significantly increased catalase (CAT) activity and glutathione (GSH) levels in both haemocyte lysate supernatant (intracellular) and plasma supernatant (extracellular)[6].
In vivo, [Leu5]-Enkephalin (1mg/kg) administered via subcutaneous injection in a mouse model of colorectal distension-induced visceral pain significantly reduced the visceromotor response elicited by 60mmHg pressure stimulation[7]. [Leu5]-Enkephalin (1fM; 5μL) co-administered intrathecally with the peptidase inhibitors phosphoramidon (2nM) and bestatin (0.25nM) in ddY-strain mice induced characteristic nociceptive behaviors (scratching, biting, licking), which peaked at 10-15min and gradually subsided within 30min[8].
References:
[1] HOHENWARTER L, PUIL E, ROUHOLLAHI E, et al. A Novel Leu-Enkephalin Prodrug Produces Pain-Relieving and Antidepressant Effects[J]. Molecular Pharmaceutics, 2024, 21(2): 688-703.
[2] CULLEN J M, CASCELLA M. Physiology, enkephalin[J]. 2020.
[3] MIURA M, YOSHIKAWA M, WATANABE M, et al. Increase in antinociceptive effect of [leu5] enkephalin after intrathecal administration of mixture of three peptidase inhibitors[J]. Tokai Journal of Experimental and Clinical Medicine, 2013, 38(2): 62-70.
[4] VISWANADHAM K K D R, BÖTTGER R, HOHENWARTER L, et al. An effective and safe enkephalin analog for antinociception[J]. Pharmaceutics, 2021, 13(7): 927.
[5] YANG D J, LEE K S, KO C M, et al. Leucine-enkephalin promotes wound repair through the regulation of hemidesmosome dynamics and matrix metalloprotease[J]. Peptides, 2016, 76: 57-64.
[6] LIU D. Effects of Leucine-enkephalin on catalase activity and glutathione level in haemolymph of the scallop Chlamys farreri[J]. International Journal of Peptide Research and Therapeutics, 2008, 14(1): 16-20.
[7] FABISIAK A, SOBOCIŃSKA M, KAMYSZ E, et al. Antinociceptive potency of enkephalins and enkephalinase inhibitors in the mouse model of colorectal distension—proof-of-concept[J]. Chemical Biology & Drug Design, 2018, 92(1): 1387-1392.
[8] KOMATSU T, KATSUYAMA S, MIZOGUCHI H, et al. Spinal ERK2 activation through δ₂-opioid receptors contributes to nociceptive behavior induced by intrathecal injection of leucine-enkephalin[J]. Peptides, 2014, 54: 131-139.
[Leu5]-Enkephalin是一种通过与阿片受体结合以调节疼痛感知和情绪的内源性δ阿片受体激动剂[1,2]。[Leu5]-Enkephalin通常用于新型镇痛药物的开发及神经退行性疾病的治疗和研究[3,4]。
在体外，[Leu5]-Enkephalin（5-50μM）处理人永生化角质形成HaCaT细胞21h，能显著促进细胞的迁移和划痕伤口的闭合。[Leu5]-Enkephalin（20μM）处理HaCaT细胞24h，能显著上调基质金属蛋白酶MMP-2和MMP-9的基因表达水平[5]。[Leu5]-Enkephalin（50μg/mL）处理扇贝Chlamys farreri血淋巴1h，能显著提升血淋巴细胞裂解上清液（细胞内）和血浆上清液（细胞外）中过氧化氢酶（CAT）的活性和谷胱甘肽（GSH）的水平[6]。
在体内，[Leu5]-Enkephalin（1mg/kg）通过皮下注射处理结直肠扩张诱导的内脏疼痛小鼠模型，显著降低了由60mmHg压力刺激引起的内脏运动反应[7]。[Leu5]-Enkephalin（1fM; 5μL）与肽酶抑制剂phosphoramidon（2nM）和bestatin（0.25nM）联合鞘内注射ddY品系小鼠，可诱导典型的伤害性行为（抓挠、咬、舔），该行为在10-15min达到峰值，并在30min内逐渐消失[8]。
| Cell experiment [1]: | |
Cell lines | HaCaT cells |
Preparation Method | Cells were plated in six-well plates and grown to confluence at 37°C. A scratch wound was created by scraping the cell monolayer with a P100 pipet tip. Cells were washed once and incubated with 2mL of growth media containing [Leu5]-Enkephalin (5-50μM). After 21h, images were acquired immediately using an AxioObserver FL microscope at ×10 magnification. |
Reaction Conditions | 5, 10, 20, and 50μM; 21h |
Applications | All the doses tested showed positive wound healing effect with 20μM of [Leu5]-Enkephalin being most remarkable. HaCaT cells migrated steadily across the wound from both sides, moving as an orderly sheet of cells with a smooth leading edge. Cell movement was significantly accelerated by treatment with [Leu5]-Enkephalin in a time dependent manner. |
| Animal experiment [2]: | |
Animal models | Pathogen-free adult male ddY-strain mice |
Preparation Method | Intrathecal i.t. injection of [Leu5]-Enkephalin with phosphoramidon (2nM) and bestatin (0.25nM) in mice. The duration of scratching, biting and licking response induced by [Leu5]-Enkephalin (1fM) in combination with phosphoramidon and bestatin was measured every 5min for the 30min period starting immediately after i.t. injection. |
Dosage form | 1fM; 5μL; i.t. |
Applications | The nociceptive responses induced by i.t. combined injection of [Leu5]-Enkephalin with peptidase inhibitors peaked at 10-15min and declined progressively until cessation at 30min post-i.t. injection. |
References: | |
| Cas No. | 58822-25-6 | SDF | |
| 别名 | 亮氨酸脑啡肽,Leu-enkephalin; Leucine enkephalin; Leucyl-enkephalin | ||
| 化学名 | (2S,5R,14S)-14-amino-5-benzyl-15-(4-hydroxyphenyl)-2-isobutyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic acid | ||
| Canonical SMILES | O=C([C@@H](CC1=CC=CC=C1)NC(CNC(CNC([C@H](CC(C=C2)=CC=C2O)N)=O)=O)=O)N[C@H](C(O)=O)CC(C)C | ||
| 分子式 | C28H37N5O7 | 分子量 | 555.63 |
| 溶解度 | ≥ 55.6mg/mL in DMSO | 储存条件 | Desiccate 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 | 1.7998 mL | 8.9988 mL | 17.9976 mL |
| 5 mM | 360 μL | 1.7998 mL | 3.5995 mL |
| 10 mM | 180 μL | 899.9 μL | 1.7998 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。
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Quality Control & SDS
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- Purity: >99.50%
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