stearyl 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: stearyl carnitine ester
• 英文别名: (2-Hydroxy-4-octadecoxy-4-oxobutyl)-trimethylazanium;iodide
• 化学式: C₂₅H₅₂NO₃*I
• 分子量: 541.597
• InChiKey: VWXBFXSWFDAENG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  30
• 可旋转键数：
  22
• 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：

  油酸酐 、 stearyl 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 trimethyl-[2-[(Z)-octadec-9-enoyl]oxy-4-octadecoxy-4-oxobutyl]azanium;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：

  1-碘十八烷 、 CARNITINE 以 1,4-二氧六环 、 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 4.0h， 以81%的产率得到stearyl carnitine ester
  参考文献：
  名称：

  Stabilization of polynucleotide complexes

  摘要：

  聚核苷酸复合物通过添加一种抗冻保护剂并对所得的配方进行冻干处理来稳定。冻干配方经过研磨或筛选成为干粉配方，可用于传递聚核苷酸复合物。将聚核苷酸传递到所需细胞组织的方法是通过将粉末与组织接触以重新水合。在一个首选实施例中，使用干粉配方来诱导患者肺组织的基因修饰。

  公开号：

  EP1491217A1

文献信息

• Stabilization of polynucleotide complexes
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP1491217A1

  公开（公告）日：2004-12-29

  Polynucleotide complexes are stabilized by adding a cryoprotectant compound and lyophilizing the resulting formulation. The lyophilized formulations are milled or sieved into a dry powder formulation which may be used to deliver the polynucleotide complex. Delivery of the polynucleotide to a desired cell tissue is accomplished by contacting the tissue with the powder to rehydrate it. In a preferred embodiment, a dry powder formulation is used to induce genetic modification of a patient's lung tissue.

  聚核苷酸复合物通过添加一种抗冻保护剂并对所得的配方进行冻干处理来稳定。冻干配方经过研磨或筛选成为干粉配方，可用于传递聚核苷酸复合物。将聚核苷酸传递到所需细胞组织的方法是通过将粉末与组织接触以重新水合。在一个首选实施例中，使用干粉配方来诱导患者肺组织的基因修饰。
• Synthesis and Characterization of Long Chain Alkyl Acyl Carnitine Esters. Potentially Biodegradable Cationic Lipids for Use in Gene Delivery
  作者：Jinkang Wang、Xin Guo、Yuhong Xu、Lee Barron、Francis C. Szoka

  DOI：10.1021/jm950802i

  日期：1998.6.1

  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.