[(2S)-2,3-dihydroxypropyl] [(2R)-3-octadecoxy-2-phenylmethoxypropyl] hydrogen phosphate | 1026554-06-2

• 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: [(2S)-2,3-dihydroxypropyl] [(2R)-3-octadecoxy-2-phenylmethoxypropyl] hydrogen phosphate
• CAS: 1026554-06-2
• 化学式: C₃₁H₅₇O₈P
• 分子量: 588.763
• InChiKey: GSVJCQXDEXNQHZ-IOWSJCHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  40
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S)-2,3-dihydroxypropyl] [(2R)-3-octadecoxy-2-phenylmethoxypropyl] hydrogen phosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.5h， 以100%的产率得到1-O-octadecyl-2-hydroxy-sn-glycero-3-phospho-(S)-glycerol
  参考文献：
  名称：

  Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue

  摘要：

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.

  DOI：

  10.1021/jm049006f
• 作为产物：
  描述：

  硬脂醇 在 盐酸 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 三氟甲磺酸 、 三氟化硼乙醚 、 胸苷酸 、 三甲胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 癸烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 为溶剂， 反应 12.17h， 生成 [(2S)-2,3-dihydroxypropyl] [(2R)-3-octadecoxy-2-phenylmethoxypropyl] hydrogen phosphate
  参考文献：
  名称：

  Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue

  摘要：

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.

  DOI：

  10.1021/jm049006f