1-oleoyl-2-lysoglycerophosphocholine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1-oleoyl-2-lysoglycerophosphocholine
• 英文别名: LPC 18:1；1-Oleoylglycerophosphocholine；2-[hydroxy-[(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]phosphoryl]oxyethyl-trimethylazanium
• 化学式: C₂₆H₅₃NO₇P
• 分子量: 522.683
• InChiKey: YAMUFBLWGFFICM-PTGWMXDISA-O

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-二-正丙基乙酰基氯 、 1-oleoyl-2-lysoglycerophosphocholine 在 N,N'-dimethylaminopyridine 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 1-oleoyl-2-valproyl-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Incorporation of [3H]Valproic Acid into Lipids in GT1–7 Neurons

  摘要：

  Valproic acid (2-propylpentanoic acid, valproate, VPA), an 8-carbon, branched chain fatty acid, is effectively used in the treatment of mania and epilepsy. The biochemical mechanisms by which this drug has its therapeutic effects are not yet established. The purpose of this study was to partially characterize the incorporation of [H-3]VPA into phospholipids of GTI-7 neurons, an immortalized hypothalamic cell line. GT1-7 neurons were grown to confluence in culture dishes, and then were incubated with various concentrations of [H-3]VPA between 10 and 400 mu g/mL for various times up to 20 hr. Total lipids were extracted and phospholipids were separated from neutral lipids using TLC. Our results indicate that [H-3]VPA (10 mu g/mL) was incorporated into phospholipids of GTI-7 neurons in a time-dependent and Saturable manner over 300 min. Subsequent separation of the lipid fraction by TLC indicated that 44.4% of the radioactivity taken up by the cells was incorporated into phospholipids and neutral lipids. One of the phospholipids migrated with a slightly lower R-f value than authentic phosphatidylcholine. Our results show that the incorporation of VPA into phospholipids and glycerides was linear with VPA concentrations from 10 to 400 mu g/mL. Finally, we synthesized 1-acyl-2-valproyl-sn-glycero-3-phosphocholine and validated its structure with nuclear magnetic resonance and electrospray mass spectrometry to verify the structure of this compound, confirming that this compound is structurally possible. We conclude that VPA is incorporated into lipids in GTI-7 neurons and discuss the possible effects of valproyl phospholipids on neuronal 'functional properties. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(98)00148-8
• 作为产物：
  描述：

  1,2‐dioleoyl‐sn‐glycero‐3‐phosphocholine 在 水 作用下， 反应 0.75h， 生成 1-oleoyl-2-lysoglycerophosphocholine 、 油酸 、 9-octadecenoic acid-2′,3′-dihydroxy propyl ester 、 磷酸
  参考文献：
  名称：

  Kinetics and pathways for an algal phospholipid (1,2-dioleoyl-sn-glycero-3-phosphocholine) in high-temperature (175–350 °C) water

  摘要：

  我们研究了 1,2-二油酰-sn-甘油-3-磷酸胆碱（DOPC）在 175、200、225 和 350°C 高温水中的行为。DOPC 发生水解，生成油酸和多种含磷产物。水解作用由油酸和磷酸催化，油酸和磷酸也是反应产物。DOPC 形成 1-酰基和 2-酰基溶血磷脂酰胆碱（LPC）以及油酸作为主要产物。LPC 随后形成其他含磷中间产物，最后形成磷酸作为最终的含磷产物。在 350 ℃ 下，磷酸和油酸是唯一被观察到的产物。我们观察到油酸和甘油的酯类（9-十八烯酸-2,3-二羟基丙酯），这可能是通过水解 LPC 形成的。提出了一个反应网络来解释所观察到的产物的形成。基于所提途径的定量动力学模型与实验数据一致。

  DOI：

  10.1039/c2gc35639b

文献信息

• Means and Methods for the Treatment and Prevention of Allergic Diseases
  申请人：Braxmeier Tobias

  公开号：US20090018105A1

  公开（公告）日：2009-01-15

  The present invention relates of the use of certain inner ionic (zwitter ionic) phospholipids, phosphonolipids and phosphate derivatives for the preparation of a pharmaceutical composition for the treatment, prevention and/or amelioration of an immunological disorder related to mast cell sensitization. Preferred in this context are edelfosine and miltefosine. In a particularly preferred embodiment, the present invention relates to the use of miltefosine for the preparation of a pharmaceutical composition for the treatment, prevention and/or amelioration of allergic diseases, in particular acute hyperallergic diseases, like asthma.
• METHODS FOR THE TREATMENT AND AMELIORATION OF ATOPIC DERMATITIS
  申请人：BRAXMEIER Tobias

  公开号：US20110263531A1

  公开（公告）日：2011-10-27

  The present invention relates of the use of certain inner ionic (zwitter ionic) phospholipids, phosphonolipids and phosphate derivatives for the preparation of a pharmaceutical composition for the treatment, prevention and/or amelioration of an immunological disorder related to mast cell sensitization and/or activation. Preferred in this context are Edelfosine, Miltefosine and Perifosine. In a particularly preferred embodiment, the present invention relates to the use of Miltefosine for the preparation of a pharmaceutical composition for the treatment, prevention and/or amelioration of allergic diseases, in particular acute hyperallergic diseases, like asthma, atopic dermatitis and mastocytosis.
• US7998945B2
  申请人：——

  公开号：US7998945B2

  公开（公告）日：2011-08-16
• US8394785B2
  申请人：——

  公开号：US8394785B2

  公开（公告）日：2013-03-12
• Kinetics and pathways for an algal phospholipid (1,2-dioleoyl-sn-glycero-3-phosphocholine) in high-temperature (175–350 °C) water
  作者：Shujauddin Changi、Adam J. Matzger、Phillip E. Savage

  DOI：10.1039/c2gc35639b

  日期：——

  We examined the behavior of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) in high-temperature water at 175, 200, 225, and 350 °C. DOPC hydrolyzed to give oleic acid and a number of phosphorus-containing products. The hydrolysis was catalyzed by oleic and phosphoric acids, which were also reaction products. DOPC formed 1-acyl and 2-acyl lyso-phosphatidylcholine (LPC) along with oleic acid as primary products. LPC subsequently formed other phosphorus-containing intermediates, which finally led to phosphoric acid as the ultimate P-containing product. At 350 °C, phosphoric acid and oleic acid were the only products observed. We observed an ester of oleic acid and glycerol (9-octadecenoic-2,3-dihydroxypropyl ester), which likely formed via the hydrolysis of LPC. A reaction network is proposed to explain the formation of the observed products. A quantitative kinetics model based on the proposed pathways was consistent with the experimental data.

  我们研究了 1,2-二油酰-sn-甘油-3-磷酸胆碱（DOPC）在 175、200、225 和 350°C 高温水中的行为。DOPC 发生水解，生成油酸和多种含磷产物。水解作用由油酸和磷酸催化，油酸和磷酸也是反应产物。DOPC 形成 1-酰基和 2-酰基溶血磷脂酰胆碱（LPC）以及油酸作为主要产物。LPC 随后形成其他含磷中间产物，最后形成磷酸作为最终的含磷产物。在 350 ℃ 下，磷酸和油酸是唯一被观察到的产物。我们观察到油酸和甘油的酯类（9-十八烯酸-2,3-二羟基丙酯），这可能是通过水解 LPC 形成的。提出了一个反应网络来解释所观察到的产物的形成。基于所提途径的定量动力学模型与实验数据一致。