4,8,13,17,21-pentamethyldocosyl methanesulfonate | 848982-35-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4,8,13,17,21-pentamethyldocosyl methanesulfonate
• CAS: 848982-35-4
• 化学式: C₂₈H₅₈O₃S
• 分子量: 474.833
• InChiKey: DBOWQESHSGNZCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.01
• 重原子数：
  32.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,8,13,17,21-pentamethyldocosyl methanesulfonate 在 potassium tert-butylate 作用下， 以 乙腈 、 xylene 为溶剂， 反应 24.5h， 生成 [2,3-bis(4,8,13,17,21-pentamethyl-docosyloxy)propyl](2-hydroxyethyl)dimethylammonium bromide
  参考文献：
  名称：

  Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids

  摘要：

  We synthesized new cationic lipids, analogue to N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride (DOTMA) and 1,2-dimyristyloxypropyl-3-dimethyl-hydroxyethylammonium bromide (DMRIE), in order to compare those containing a dodecyl chain with those having a relatively long chain with two or five double bonds, such as squalenyl and dihydrofarnesyl derivatives, or complex saturated structures, such as squalane derivatives. The fusogenic helper lipid dioleoylphosphatidylethanolamine (DOPE) was added to cationic lipids to form a stable complex. Liposomes composed of 50:50 w/w cationic lipid/DOPE were prepared and incubated with plasmidic DNA at various charge ratios and the diameter and zeta potential of the complexes were measured. The surface charge of the DNA/lipid complexes can be controlled by adjusting the cationic lipid/DNA ratio. Finally, we tested the in vitro transfection efficiency of the cationic lipid/DNA complexes using different cell lines. The transfection efficiency was highest for the dodecyloxy derivative containing a single hydroxyethyl group in the head, followed by the dodecyloxy and the farnesyloxy trimethylammonium derivatives. Instead the C27 squalenyl and C27 squalanyl derivatives resulted inactive.

  DOI：

  10.1016/j.farmac.2004.06.007
• 作为产物：
  描述：

  1,1',2-trisnorsqualene alcohol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4,8,13,17,21-pentamethyldocosyl methanesulfonate
  参考文献：
  名称：

  Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids

  摘要：

  We synthesized new cationic lipids, analogue to N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride (DOTMA) and 1,2-dimyristyloxypropyl-3-dimethyl-hydroxyethylammonium bromide (DMRIE), in order to compare those containing a dodecyl chain with those having a relatively long chain with two or five double bonds, such as squalenyl and dihydrofarnesyl derivatives, or complex saturated structures, such as squalane derivatives. The fusogenic helper lipid dioleoylphosphatidylethanolamine (DOPE) was added to cationic lipids to form a stable complex. Liposomes composed of 50:50 w/w cationic lipid/DOPE were prepared and incubated with plasmidic DNA at various charge ratios and the diameter and zeta potential of the complexes were measured. The surface charge of the DNA/lipid complexes can be controlled by adjusting the cationic lipid/DNA ratio. Finally, we tested the in vitro transfection efficiency of the cationic lipid/DNA complexes using different cell lines. The transfection efficiency was highest for the dodecyloxy derivative containing a single hydroxyethyl group in the head, followed by the dodecyloxy and the farnesyloxy trimethylammonium derivatives. Instead the C27 squalenyl and C27 squalanyl derivatives resulted inactive.

  DOI：

  10.1016/j.farmac.2004.06.007