3-[2,3,4,5,6-Pentakis(3-hydroxypropoxy)cyclohexyl]oxypropan-1-ol | 1107651-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2,3,4,5,6-Pentakis(3-hydroxypropoxy)cyclohexyl]oxypropan-1-ol
• CAS: 1107651-12-6
• 化学式: C₂₄H₄₈O₁₂
• 分子量: 528.638
• InChiKey: LYYQLNVYIWCEAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  36
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-[2,3,4,5,6-Pentakis(3-hydroxypropoxy)cyclohexyl]oxypropan-1-ol 在 sodium hydride 作用下， 生成 3-[2-[3-[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]propoxy]-3,4,5,6-tetrakis(3-methylsulfonyloxypropoxy)cyclohexyl]oxypropyl methanesulfonate
  参考文献：
  名称：

  Novel synthetic LPDs consisting of different cholesterol derivatives for gene transfer into hepatocytes

  摘要：

  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.

  DOI：

  10.3109/10611860903548370
• 作为产物：
  描述：

  sexi-(β-carbethoxyethyl) cyclohexanehexol ether 在 lithium aluminium tetrahydride 作用下， 生成 3-[2,3,4,5,6-Pentakis(3-hydroxypropoxy)cyclohexyl]oxypropan-1-ol
  参考文献：
  名称：

  Novel synthetic LPDs consisting of different cholesterol derivatives for gene transfer into hepatocytes

  摘要：

  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.

  DOI：

  10.3109/10611860903548370

文献信息

• Synthesis of Multivalent Galactosides as Targeting Ligand for Gene Delivery
  作者：Li Hai、Zhi-Rong Zhang、Shan Wang、Xiang Xiao、Yong Wu

  DOI：10.1080/00397910903161827

  日期：2010.5.19

  A series of novel bifunctional glycolipid ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and assayed in vitro on human hepatoma cells, HepG2, derived from parenchymal liver cells. The compounds bear five -linked Gal moieties linked to the core scaffold, hexa-antennary alcohol, for interaction with the binding site of the ASGP-R. The liposome/DNA complexes containing the glycolipid ligands are efficiently recognized by ASGP-R and exhibited high affinity and transfection activity.