1-(5-cholesten-3α-yloxy)-17-(2H-tetrahydropyran-2-yloxy)-3n³₁₅-pentaoxaheptadecane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-(5-cholesten-3α-yloxy)-17-(2H-tetrahydropyran-2-yloxy)-3n³₁₅-pentaoxaheptadecane
• 英文别名: 2-[2-[2-[2-[2-[2-[2-[[(3R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]oxane
• 化学式: C₄₄H₇₈O₈
• 分子量: 735.099
• InChiKey: BPIBVWDKLMOHKY-YBSAXHATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(5-cholesten-3α-yloxy)-17-(2H-tetrahydropyran-2-yloxy)-3n³₁₅-pentaoxaheptadecane 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以84%的产率得到17-(5-cholesten-3α-yloxy)-3n³₁₅-pentaoxaheptadecan-1-ol
  参考文献：
  名称：

  Synthesis of Cholesterylated Thiogalactosides for Gene Delivery

  摘要：

  A series of cholesterylated thiogalactosides L-1 - L-6 the cell targeting ligands for gene delivery to hepatocytes, was synthesized. Related poly( ethylene glycol) chain was used as a bridge for the attachment of galactoside on one hydroxyl end, while the other hydroxyl end was linked with cholesterol. This design provided an effective entry for the synthesis of a poly( ethylene glycol) compound with the hepatocyte targeting.

  DOI：

  10.1080/00397910600764634
• 作为产物：
  描述：

  四氢吡喃醚-三聚乙二醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 1-(5-cholesten-3α-yloxy)-17-(2H-tetrahydropyran-2-yloxy)-3n³₁₅-pentaoxaheptadecane
  参考文献：
  名称：

  Synthesis of Cholesterylated Thiogalactosides for Gene Delivery

  摘要：

  A series of cholesterylated thiogalactosides L-1 - L-6 the cell targeting ligands for gene delivery to hepatocytes, was synthesized. Related poly( ethylene glycol) chain was used as a bridge for the attachment of galactoside on one hydroxyl end, while the other hydroxyl end was linked with cholesterol. This design provided an effective entry for the synthesis of a poly( ethylene glycol) compound with the hepatocyte targeting.

  DOI：

  10.1080/00397910600764634

文献信息

• Synthesis of Cholesterylated Thiogalactosides for Gene Delivery
  作者：Li Hai、Jiang Fan、Zhirong Zhang、Guoyao Zhang、Yong Wu

  DOI：10.1080/00397910600764634

  日期：2006.9

  A series of cholesterylated thiogalactosides L-1 - L-6 the cell targeting ligands for gene delivery to hepatocytes, was synthesized. Related poly( ethylene glycol) chain was used as a bridge for the attachment of galactoside on one hydroxyl end, while the other hydroxyl end was linked with cholesterol. This design provided an effective entry for the synthesis of a poly( ethylene glycol) compound with the hepatocyte targeting.
• Novel synthetic LPDs consisting of different cholesterol derivatives for gene transfer into hepatocytes
  作者：Jiao Lu、Di Zhu、Zhi-Rong Zhang、Li Hai、Yong Wu、Xun Sun

  DOI：10.3109/10611860903548370

  日期：2010.8

  In the present study, LPDs composing of a series of novel synthetic cholesterylated derivatives bearing a cluster of galactose residues and different spacer lengths were prepared for performing target gene delivery to hepatocytes and their physiochemical properties as well as gene transfer efficiency were investigated. In agreement with the "clustering effect" known to occur with more complex oligomeric structures, the addition of galactose residues under optimized spatial arrangement condition invariably increased the transfect efficiency into hepatoma cells, which can be owed to the sufficient binding of galactose ligands to the ASGPR on hepatocytes. However, the gene transfer ability to hepatocytes was not always improved with extended spacer arms, suggesting a spatial binding sites arrangement of the receptor. Moreover, our research has established galactosylated LPDs, specifically, LPDIIb, LPDIIIc, and LPDIVe as potential vectors to deliver special genes into hepatocytes with low toxicity, combining the condensing effect of protamine and the targeting capability of cholesterylated thiogalactosides.