dimyristylphosphate anhydride | 864523-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: dimyristylphosphate anhydride
• 英文别名: Di(tetradecoxy)phosphoryl ditetradecyl phosphate；di(tetradecoxy)phosphoryl ditetradecyl phosphate
• CAS: 864523-82-0
• 化学式: C₅₆H₁₁₆O₇P₂
• 分子量: 963.48
• InChiKey: OWBUIMKZCDTRSX-UHFFFAOYSA-N

物化性质

• 沸点：
  824.8±34.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  25.6
• 重原子数：
  65
• 可旋转键数：
  58
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  二肉豆蔻醇磷酸酯 在 吡啶 作用下， 反应 2.5h， 以75%的产率得到dimyristylphosphate anhydride
  参考文献：
  名称：

  POLYCATIONIZED PHOSPHOLIPID DERIVATIVES

  摘要：

  本发明提供了新颖的磷脂衍生物。此外，本发明提供了在细胞内具有出色的基因/核酸引入效率的脂质膜结构。

  公开号：

  US20100094020A1

文献信息

• POLYCATIONIZED PHOSPHOLIPID DERIVATIVES
  申请人：DEWA Takehisa

  公开号：US20100094020A1

  公开（公告）日：2010-04-15

  The present invention provides novel phospholipid derivatives. Furthermore, the present invention provides lipid membrane structures excellent in gene/nucleic acid introduction efficiency into a cell.

  本发明提供了新颖的磷脂衍生物。此外，本发明提供了在细胞内具有出色的基因/核酸引入效率的脂质膜结构。
• US8143413B2
  申请人：——

  公开号：US8143413B2

  公开（公告）日：2012-03-27
• Liposomal Polyamine−Dialkyl Phosphate Conjugates as Effective Gene Carriers: Chemical Structure, Morphology, and Gene Transfer Activity
  作者：Takehisa Dewa、Tomohiro Asai、Yuka Tsunoda、Kiyoshi Kato、Daisuke Baba、Misa Uchida、Ayumi Sumino、Kayoko Niwata、Takuya Umemoto、Kouji Iida、Naoto Oku、Mamoru Nango

  DOI：10.1021/bc900376y

  日期：2010.5.19

  Synthetic cationic lipids are promising transfection agents for gene therapy. We report here that polyamine conjugates of dialkyl phosphates, combined with natural lipids and assembled in the form of liposomes (polycationic liposome: PCL), possess high transfection activity in the COS-1 cell line. Furthermore, we describe the functional morphology of the PCL/DNA complexes as revealed by atomic force microscopy (AFM). The conjugates were synthesized from dialkyl phosphates (with alkyl chain lengths of 12, 14, or 16 carbons) by reaction with the polyamine molecules, spermidine, spermine, or polyethylenimine (PEI(1800)). [Dewa, T., et al. Bioconjugate Chem. 2004, 15, 824]. The PCL composed of the spermidine and C16 conjugate combined with phospholipid and cholesterol (conjugate/phospholipid/cholesterol = 1/1/1 as a molar ratio) exhibited 3.6 times higher activity than that of a popular commercial product. Systematic tests revealed clear correlations of the transgene activity with physical properties of the polyamine, in particular, that longer alkyl chains and the lower molecular weight polyamines (spermidine, spermine) favor high efficacy at the higher nitrogen/phosphate ratio = 24 (N/P, stoichiometric ratio of nitrogen in the conjugate to phosphate in DNA). The low molecular weight polyamine-based PCLs, which formed 150-400 nm particles with plasmid DNA (lipoplexes), exhibited similar to 3-fold higher gene transfer activity than micellar aggregates (lacking phospholipid and cholesterol) of the corresponding conjugate. In contrast, the PEI-based PCL formed large aggregates (similar to 1 mu m), that, like the micellar aggregate form, had low activity. Activity of the low molecular weight polyamine-based PCLs increased linearly with the NIP of the lipoplex up to N/P = 24. Formation of lipoplexes was examined by agarose gel electrophoresis, dynamic light scattering (DLS), and AFM. At the lower N/P = 5, large aggregates of complex ( I urn), in which DNA molecules were loosely packed, were observed. At higher NIP, lipoplexes were converted into smaller particles (150-400 nin) having a lamellar structure, in which DNA molecules were tightly packed. Such morphological features of the lipoplex correlate with the dependence of transfection on the N/P in that the lamellar structures gave superior transfection. AFM also indicated that the lipoplexes disassembled significantly. releasing DNA, when the lipoplexes were exposed to acidic conditions (pH 4). The significance for transfection activity of the metamorphosis of bilayer lipoplexes is discussed relative to that of the less active micellar aggregate form, which is unresponsive to pH change.