Lysophosphatidylcholine (LPC, CAS 9008-30-4)
Lysophosphatidylcholine (LPC, CAS 9008-30-4) is a glycerophospholipid formed by phospholipase-mediated hydrolysis of phosphatidylcholine. As a critical extracellular signaling molecule, LPC regulates inflammation, cell proliferation, and angiogenesis. Clinically, it is implicated in metabolic disorders, neurodegenerative diseases, and cardiovascular pathologies, while also serving as a therapeutic target and diagnostic biomarker.溶血磷脂酰胆碱（LPC，CAS 9008-30-4）是磷脂酰胆碱经磷脂酶水解生成的甘油磷脂，作为关键细胞外信号分子调控炎症、细胞增殖及血管生成。临床研究显示其与代谢紊乱、神经退行性疾病及心血管病变密切相关，同时是药物开发与疾病诊断的重要靶点及生物标志物。
Basic Information
- Chemical Name: Lysophosphatidylcholine (LPC)
- CAS Number: 9008-30-4
- Molecular Formula: C₁₈H₃₄NO₇P (for 1-hexanoyl-2-hydroxy-sn-glycero-3-phosphocholine)
- Molecular Weight: 355.36–522.48 g/mol (varies with fatty acid chain length)
- Appearance: White to off-white powder or viscous solution
- 化学名称：溶血磷脂酰胆碱
- CAS号：9008-30-4
- 分子式：C₁₈H₃₄NO₇P（以1-己酰基-2-羟基-sn-甘油-3-磷酸胆碱为例）
- 分子量：355.36–522.48 g/mol（因脂肪酸链长度而异）
- 性状：白色至类白色粉末或粘稠溶液
2. Key Physicochemical Properties
| Parameter | Details |
|---|---|
| Solubility | Highly water-soluble; forms micelles in aqueous solutions. |
| Surface Activity | Amphiphilic structure enables emulsification and membrane interaction. |
| Stability | Stable under physiological pH (6–8); susceptible to oxidation. |
| 参数 | 详情 |
|---|---|
| 溶解性 | 高度水溶性，水溶液中可形成胶束。 |
| 表面活性 | 两亲性结构赋予其乳化及膜相互作用能力。 |
| 稳定性 | 生理pH（6–8）下稳定；易被氧化破坏。 |
3. Mechanisms of Action
- Signaling Pathways:
- Binds G-protein-coupled receptors (e.g., LPAR1-6) to regulate cell proliferation and migration 16.
- Activates Rho/ROCK and PI3K/Akt pathways, influencing angiogenesis and tumor progression 14.
- Metabolic Roles:
- Modulates insulin resistance and glucose metabolism in polycystic ovary syndrome (PCOS) 3.
- Stabilizes α-synuclein (α-syn) in its native helical structure, preventing pathological aggregation in Parkinson’s disease 4.
- 信号通路：
- 结合G蛋白偶联受体（如LPAR1-6）调控细胞增殖与迁移16。
- 激活Rho/ROCK及PI3K/Akt通路，影响血管生成与肿瘤进展14。
- 代谢功能：
- 调节多囊卵巢综合征（PCOS）中的胰岛素抵抗及葡萄糖代谢3。
- 稳定α-突触核蛋白（α-syn）的天然螺旋构象，抑制其在帕金森病中的病理性聚集4。
4. Applications
- Therapeutic:
- Neurodegeneration: Inhibits α-syn aggregation, offering potential treatment for Parkinson’s disease 4.
- Cardiovascular: Reduces atherosclerotic plaque inflammation by modulating macrophage phenotype 6.
- Diagnostic:
- Biomarker for insulin resistance, type 2 diabetes, and coronary artery disease 3.
- Industrial:
- Drug delivery enhancer for transdermal formulations due to enhanced skin permeation 57.
- 治疗应用：
- 神经退行性疾病：抑制α-syn聚集，为帕金森病提供潜在疗法4。
- 心血管疾病：通过调节巨噬细胞表型减轻动脉粥样硬化斑块炎症6。
- 诊断应用：
- 胰岛素抵抗、2型糖尿病及冠心病的生物标志物3。
- 工业应用：
- 作为透皮制剂药物递送的渗透增强剂57。
5. Production & Engineering
- Natural Sources:
- Isolated from egg yolk phospholipids (75% phosphatidylcholine) or soybean lecithin 19.
- Synthetic Methods:
- Enzymatic Hydrolysis: Phospholipase A2 treatment of phosphatidylcholine 110.
- Chemical Synthesis: Phosphorylation of lysophosphatidylethanolamine using POCl₃ 7.
- Biotechnological: Engineered E. coli strains overexpressing autotaxin (ENPP2) for LPA/LPC production 1.
- 天然来源：
- 从蛋黄磷脂（含75%磷脂酰胆碱）或大豆卵磷脂中提取19。
- 合成方法：
- 酶解法：磷脂酶A2水解磷脂酰胆碱110。
- 化学合成：POCl₃催化溶血磷脂乙醇胺磷酸化7。
- 生物技术：改造大肠杆菌过表达自分泌运动因子（ENPP2）生产LPC/LPA1。
6. Safety & Challenges
- Safety: GRAS (Generally Recognized as Safe) at ≤10 μM; high doses (>50 μM) induce hemolysis 27.
- Challenges:
- Rapid enzymatic degradation in vivo (half-life <2 h) 1.
- Costly large-scale synthesis and purification 5.
- 安全性：≤10 μM浓度下视为安全；高剂量（>50 μM）引发溶血27。
- 挑战：
- 体内酶解迅速（半衰期<2小时）1。
- 大规模合成与纯化成本高昂5。
7. Research Frontiers
- Neuroprotection: LPC stabilizes α-syn in Parkinson’s models, reducing Lewy body formation 4.
- Metabolic Syndrome: Low plasma LPC 18:2 predicts insulin resistance and cardiovascular risks 3.
- Drug Delivery: LPC-loaded nanoparticles for sustained release in ocular and dermal therapies 57.
- 神经保护：LPC在帕金森病模型中稳定α-syn，减少路易小体形成4。
- 代谢综合征：血浆LPC 18:2水平降低可预测胰岛素抵抗及心血管风险3。
- 药物递送：LPC纳米颗粒用于眼部及皮肤疾病的缓释治疗57。
8. Regulatory Status
- FDA: Generally Recognized as Safe (GRAS) for cosmetic and dietary applications.
- EU: Approved as a food additive (E470a) in limited concentrations.
sale@pharma-peptides.com
请到「后台-用户-个人资料」中填写个人说明。