palmityl carnitine ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: palmityl carnitine ester
• 英文别名: (4-Hexadecoxy-2-hydroxy-4-oxobutyl)-trimethylazanium;iodide
• 化学式: C₂₃H₄₈NO₃*I
• 分子量: 513.544
• InChiKey: VPEIRNAMWNXEPA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  28
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  棕榈酸酐 、 palmityl carnitine ester 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 96.0h， 生成 (2-Hexadecanoyloxy-3-hexadecyloxycarbonyl-propyl)-trimethyl-ammonium; iodide
  参考文献：
  名称：

  Synthesis and Characterization of Long Chain Alkyl Acyl Carnitine Esters. Potentially Biodegradable Cationic Lipids for Use in Gene Delivery

  摘要：

  A series of alkyl acyl carnitine esters (alkyl 3-acyloxy-4-trimethylammonium butyrate chloride) were synthesized as potential biocompatible cationic lipids for use in gene transfer. The physicochemical properties of the lipids, :liposomes prepared from them, and their complexes with DNA were characterized by differential scanning calorimetry (DSC), particle size, zeta potential, and surface monolayer measurements. The transition temperatures and behavior at an air-water interface for this series are similar to phosphatidylcholines with the same hydrocarbon chain length. The physical properties of the L derivatives were not significantly different from the DL derivatives. At 70 degrees C, the acyl chains were readily hydrolyzed at pH 7. The influence of the aliphatic chain length (n = 12-18) on transfection efficiency in vitro was determined using cationic liposomes prepared from these lipids or their mixtures with the helper lipids, dioleoylphosphatidyl ethanolamine (DOPE), dioleoylphosphatidylcholine, monooleoylglycerol, and cholesterol (Chol). The mixture of myristyl 3-myristoyloxy-4-trimethylammonium butyrate chloride (MMCE, 4d) with DOPE at a 1:1 molar ratio mediated the highest transfection efficiency in cell culture. The mixture of oleyl 3-oleoyloxy-4-trimethylammonium butyrate chloride (OOCE, 4f) with Chol at a 1:1 molar ratio gave the highest transfection efficiency after intravenous administration in mice. In vivo gene expression using 4f was comparable to values obtained with the best cationic lipids reported to date.

  DOI：

  10.1021/jm950802i
• 作为产物：
  描述：

  碘十六烷 、 CARNITINE 以65%的产率得到palmityl carnitine ester
  参考文献：
  名称：

  Dry powder formulations of polynucleotide complexes

  摘要：

  多核苷酸复合物通过添加保护冷冻剂化合物并冻干得到的配方稳定。冻干的配方经过磨粉或筛分成为干粉配方，可用于输送多核苷酸复合物。将干粉配方与所需细胞组织接触以重新水合，从而实现将多核苷酸输送到所需的细胞组织。在一种优选实施例中，干粉配方用于将遗传信息传递到呼吸道细胞。

  公开号：

  US05811406A1