1,2-dioleoyl-sn-glycero-3-phosphocholine | 56648-95-4

• 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: 1,2-dioleoyl-sn-glycero-3-phosphocholine
• 英文别名: L-α-dioleoylphosphatidyl choline；1,2-Dioleyl-sn-glycero-phosphocholin；dioleoylphosphatidylcholine；DOPC；1,2-di-(9-octadecenoyl)-sn-glycero-3-phosphocholine；[(2R)-2,3-di(octadec-9-enoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 56648-95-4
• 化学式: C₄₄H₈₄NO₈P
• 分子量: 786.127
• InChiKey: SNKAWJBJQDLSFF-HUESYALOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  54
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-dioleoyl-sn-glycero-3-phosphocholine 在 吡啶 、 sodium acetate 、 sodium dodecyl-sulfate 、 溶剂黄146 、 calcium chloride 作用下， 以 乙醚 为溶剂， 反应 336.0h， 生成 1-β-D-arabinofuranosylcytosine 5'-diphosphate-L-1,2-diolein
  参考文献：
  名称：

  Phospholipid-nucleoside conjugates. 3. Syntheses and preliminary biological evaluation of 1-.beta.-D-arabinofuranosylcytosine 5'-monophosphate-L-1,2-dipalmitin and selected 1-.beta.-D-arabinofuranosylcytosine 5'-diphosphate-L-1,2-diacylglycerols

  摘要：

  Several new phospholipid-ara-C conjugates have been prepared and tested as prodrugs of the parent ara-C. The new derivative include ara-CMP-L-dipalmitin, ara-CDP-L-distearin, ara-CDP-L dimyristin, ara-CDP-L-diolein, and the radioactively labeled derivative ara-CDP-L-di[1-14C]palmitin. In addition, the unusually stable ara-CMP-L-dipalmitin-N-phosphoryldicyclohexylurea adduct was isolated as a crystalline solid (two diastereomers) in the reaction sequence to prepare ara-CMP-L-dipalmitin. The new prodrugs were solubilized by sonication methods and tested for their antiproliferative activity in vitro against mouse myeloma MPC-11 cells and against L1210 lymphoid leukemia. Such studies demonstrated that the antiproliferative activities of the prodrugs (as determined by ED50) were less that ara-C on a molar basis. In the mouse myeloma cell line some evidence was obtained that the antiproliferative activity was related to the chain length of the fatty acid side chains in the prodrugs. In in vivo studies against L1210 lymphoid leukemia in mice, the prodrugs were shown to be much more effective than ara-C, with the overall efficacy apparently being independent of the length of the fatty acid side chain. Some evidence was obtained in the vivo studies that the ara-CDP-L-dimyristin, which bears the shortest fatty acid side chain, was more toxic at the higher dosages than the longer chain length derivatives.

  DOI：

  10.1021/jm00353a010
• 作为产物：
  描述：

  在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 1,2-dioleoyl-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

  摘要：

  The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

  DOI：

  10.1021/jacs.5b05832

文献信息

• Lachmann, Uwe; Murawski, Detlef, Zeitschrift fur Chemie, 1980, vol. 20, # 10, p. 373
  作者：Lachmann, Uwe、Murawski, Detlef

  DOI：——

  日期：——