Gly-TRISGal₃ | 220886-07-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Gly-TRISGal₃
• 英文别名: N-[3-[3-[2-[(2-aminoacetyl)amino]-3-[3-oxo-3-[3-[5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]propoxy]-2-[[3-oxo-3-[3-[5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]propoxy]methyl]propoxy]propanoylamino]propyl]-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanamide
• CAS: 220886-07-7
• 化学式: C₅₇H₁₀₄N₈O₂₈
• 分子量: 1349.49
• InChiKey: MADKVHKNKPOZEF-AYELIMADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.1
• 重原子数：
  93
• 可旋转键数：
  50
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  556
• 氢给体数：
  20
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  N-(3β-(oleoyloxy)-5-cholenoyl)-4-aminobutyric acid 、 Gly-TRISGal₃ 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以24%的产率得到[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-[[4-[[2-[[1,3-bis[3-oxo-3-[3-[5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]propoxy]-2-[[3-oxo-3-[3-[5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]propoxy]methyl]propan-2-yl]amino]-2-oxoethyl]amino]-4-oxobutyl]amino]-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate
  参考文献：
  名称：

  Design and Synthesis of Novel Amphiphilic Dendritic Galactosides for Selective Targeting of Liposomes to the Hepatic Asialoglycoprotein Receptor

  摘要：

  A series of glycolipids have been prepared which contain a cluster galactoside moiety with high affinity for the hepatic asialoglycoprotein receptor and a bile acid eater moiety which mediates stable incorporation into liposomes. Loading of liposomes with these glycolipids at a ratio of 5% (w/w) resulted in efficient recognition and uptake of the liposomes by the liver. Preinjection with asialofetuin almost completely inhibited the uptake, establishing that the liposomes were selectively recognized and processed by the asialoglycoprotein receptor on liver parenchymal cells. In contrast, a glycolipid content of 50% (w/w) led to a liver uptake that could not be inhibited by preinjection with asialofetuin, indicating that the liposomes were now processed by the Gal/Fuc-recognizing receptor on liver macrophages. The results presented in this study are important for future targeting of water-soluble and amphiphilic drugs, enveloped in these glycolipid-laden liposomes, to parenchymal liver cells.

  DOI：

  10.1021/jm981078h
• 作为产物：
  描述：

  Z-Gly-TRISGal₃ 在 palladium on activated charcoal 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 Gly-TRISGal₃
  参考文献：
  名称：

  Design and Synthesis of Novel Amphiphilic Dendritic Galactosides for Selective Targeting of Liposomes to the Hepatic Asialoglycoprotein Receptor

  摘要：

  A series of glycolipids have been prepared which contain a cluster galactoside moiety with high affinity for the hepatic asialoglycoprotein receptor and a bile acid eater moiety which mediates stable incorporation into liposomes. Loading of liposomes with these glycolipids at a ratio of 5% (w/w) resulted in efficient recognition and uptake of the liposomes by the liver. Preinjection with asialofetuin almost completely inhibited the uptake, establishing that the liposomes were selectively recognized and processed by the asialoglycoprotein receptor on liver parenchymal cells. In contrast, a glycolipid content of 50% (w/w) led to a liver uptake that could not be inhibited by preinjection with asialofetuin, indicating that the liposomes were now processed by the Gal/Fuc-recognizing receptor on liver macrophages. The results presented in this study are important for future targeting of water-soluble and amphiphilic drugs, enveloped in these glycolipid-laden liposomes, to parenchymal liver cells.

  DOI：

  10.1021/jm981078h