all-(E)-1-O-(15'-phenylpentadeca-8',10',12',14'-tetraenyl)-2-O-methyl-rac-glycero-3-phosphocholine

• 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: all-(E)-1-O-(15'-phenylpentadeca-8',10',12',14'-tetraenyl)-2-O-methyl-rac-glycero-3-phosphocholine
• 英文别名: [2-methoxy-3-[(8E,10E,12E,14E)-15-phenylpentadeca-8,10,12,14-tetraenoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
• 化学式: C₃₀H₄₈NO₆P
• 分子量: 549.688
• InChiKey: OJVOPJDXTGHVDQ-FVSXFYMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  all-(E)-5-methoxy-2-(14'-phenyltetradeca-7',9',11',13'-tetraenyl)-[1,3]dioxane 在 二异丁基氢化铝 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成 all-(E)-1-O-(15'-phenylpentadeca-8',10',12',14'-tetraenyl)-2-O-methyl-rac-glycero-3-phosphocholine
  参考文献：
  名称：

  Fluorescent Phenylpolyene Analogues of the Ether Phospholipid Edelfosine for the Selective Labeling of Cancer Cells

  摘要：

  Edelfosine (ET-18-OCH3), a synthetic antitumor ether lipid, is taken up by malignant but not by normal cells, triggering apoptosis in a large variety of human tumor cells. The synthesis of the first fluorescent edelfosine analogue (6), with apoptotic activity comparable to that of the parent drug, is described. Fluorescence microscopy experiments show that 6 selectively labels human cancer cells, accumulating into specific domains of the plasma membrane.

  DOI：

  10.1021/jm049808a

文献信息

• Synthesis and Biological Evaluation of Fluorescent Leishmanicidal Analogues of Hexadecylphosphocholine (Miltefosine) as Probes of Antiparasite Mechanisms
  作者：José M. Saugar、Javier Delgado、Valentín Hornillos、Juan R. Luque-Ortega、Francisco Amat-Guerri、A. Ulises Acuña、Luis Rivas

  DOI：10.1021/jm070595+

  日期：2007.11.1

  The leishmanicidal mechanism of miltefosine (hexadecylphosphocholine, MT) is not clearly understood. Valuable insights into its mode of action could be obtained by fluorescence techniques, given suitably emitting analogues. In this regard, the synthesis and biological characterization of two fully competent NIT fluorescent analogues is reported here: all-(E)-13-phenyltrideca-6,8,10,12-tetraenylphosphocholine (PTE-MT) and all(E)-13-phenyltrideca-8,10,12-trien-6-ynylphosphocholine (PTRI-MT). Both compounds show large absorption coefficients and a,modest, but usable, fluorescence yield. Their activities were very similar to that of NIT and were recognized by the NIT uptake system of Leishmania. Their localization in living L. donovani promastigotes by confocal microscopy show a homogeneous intracellular distribution of the fluorescence. The concentration of PTRI-MT within the parasites (ca. 1.7 mM) showed a 100-fold enrichment relative to its external concentration. These results are consistent with a multiple target leishmanicidal mechanism for NIT and validate the application of these analogues for pharmacokinetic and diagnostic studies concerning the chemotherapy of leishmaniasis.
• Fluorescent Phenylpolyene Analogues of the Ether Phospholipid Edelfosine for the Selective Labeling of Cancer Cells
  作者：Ernesto Quesada、Javier Delgado、Consuelo Gajate、Faustino Mollinedo、A. Ulises Acuña、Francisco Amat-Guerri

  DOI：10.1021/jm049808a

  日期：2004.10.1

  Edelfosine (ET-18-OCH3), a synthetic antitumor ether lipid, is taken up by malignant but not by normal cells, triggering apoptosis in a large variety of human tumor cells. The synthesis of the first fluorescent edelfosine analogue (6), with apoptotic activity comparable to that of the parent drug, is described. Fluorescence microscopy experiments show that 6 selectively labels human cancer cells, accumulating into specific domains of the plasma membrane.