1-O-oleoyl-2(R)-O-methyl-sn-glycero-3-phosphothionate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-oleoyl-2(R)-O-methyl-sn-glycero-3-phosphothionate
• 英文别名: (R)-2-Methoxy-3-(thiophosphonooxy)propyl oleate；[(2R)-3-dihydroxyphosphinothioyloxy-2-methoxypropyl] (Z)-octadec-9-enoate
• 化学式: C₂₂H₄₃O₆PS
• 分子量: 466.62
• InChiKey: FCVJYKICQNLXAX-KUFMOJEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-O-bis-(2-cyano-ethoxy)-thiophosphoryl-2(R)-O-hydroxyl-1-O-oleoyl-sn-glycerol 在 tetrafluoroboric acid 、 N,O-双三甲硅基乙酰胺 、 叔丁胺 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 48.5h， 生成 1-O-oleoyl-2(R)-O-methyl-sn-glycero-3-phosphothionate
  参考文献：
  名称：

  Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA₃ Receptor-Selective Agonist Activity

  摘要：

  The metabolically stabilized LPA analogue, 1-ole-oyl-2-O-methyl-rae-glycerophosphothioate (OMPT), is a potent agonist for the LPA(3) G-protein-coupled receptor. A new enantiospecific synthesis of both (2R)-OMPT and (2S)-OMPT is described. Calcium release assays in both LPA(3)-transfected insect Sf9 and rat hepatoma Rh7777 cells showed that (2S)OMPT was 5- to 20-fold more active than (2R)-OMPT. Similar results were found for calcium release, MAPK and Akt activation, and IL-6 release in human OVCAR3 ovarian cancer cells.

  DOI：

  10.1021/jm034207p

文献信息

• Gas-filled stabilized particles and methods of use
  申请人：Children's Medical Center Corporation

  公开号：US10577554B2

  公开（公告）日：2020-03-03

  Provided herein are various gas-filled particles having a stabilized membrane that encapsulates the gas. Pharmaceutical compositions, methods of use and treatment, and methods of preparation are also described.

  本文提供了各种充满气体的颗粒，这些颗粒具有封装气体的稳定膜。此外，还介绍了药物组合物、使用和处理方法以及制备方法。
• GAS-FILLED STABILIZED PARTICLES AND METHODS OF USE
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：US20160030596A1

  公开（公告）日：2016-02-04

  Provided herein are various gas-filled particles having a stabilized membrane that encapsulates the gas. Pharmaceutical compositions, methods of use and treatment, and methods of preparation are also described.
• Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA₃ Receptor-Selective Agonist Activity
  作者：Lian Qian、Yong Xu、Yutaka Hasegawa、Junken Aoki、Gordon B. Mills、Glenn D. Prestwich

  DOI：10.1021/jm034207p

  日期：2003.12.1

  The metabolically stabilized LPA analogue, 1-ole-oyl-2-O-methyl-rae-glycerophosphothioate (OMPT), is a potent agonist for the LPA(3) G-protein-coupled receptor. A new enantiospecific synthesis of both (2R)-OMPT and (2S)-OMPT is described. Calcium release assays in both LPA(3)-transfected insect Sf9 and rat hepatoma Rh7777 cells showed that (2S)OMPT was 5- to 20-fold more active than (2R)-OMPT. Similar results were found for calcium release, MAPK and Akt activation, and IL-6 release in human OVCAR3 ovarian cancer cells.