benzyl N-[2-[[1,3-bis[3-(3-aminopropylamino)-3-oxopropoxy]-2-[[3-(3-aminopropylamino)-3-oxopropoxy]methyl]propan-2-yl]amino]-2-oxoethyl]carbamate | 220886-04-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl N-[2-[[1,3-bis[3-(3-aminopropylamino)-3-oxopropoxy]-2-[[3-(3-aminopropylamino)-3-oxopropoxy]methyl]propan-2-yl]amino]-2-oxoethyl]carbamate
• CAS: 220886-04-4
• 化学式: C₃₂H₅₆N₈O₉
• 分子量: 696.845
• InChiKey: SERKSRBYZFHJCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  49
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  261
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy)pentanoic acid 、 benzyl N-[2-[[1,3-bis[3-(3-aminopropylamino)-3-oxopropoxy]-2-[[3-(3-aminopropylamino)-3-oxopropoxy]methyl]propan-2-yl]amino]-2-oxoethyl]carbamate 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 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[5-oxo-5-[3-[3-[3-[3-oxo-3-[3-[5-[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]propoxy]-2-[[3-oxo-3-[3-[5-[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]propoxy]methyl]-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propoxy]propanoylamino]propylamino]pentoxy]oxan-2-yl]methyl benzoate
  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：

  tris(cyanoethoxymethyl)aminomethane 在 盐酸 、 sodium hydroxide 、 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 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 生成 benzyl N-[2-[[1,3-bis[3-(3-aminopropylamino)-3-oxopropoxy]-2-[[3-(3-aminopropylamino)-3-oxopropoxy]methyl]propan-2-yl]amino]-2-oxoethyl]carbamate
  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

文献信息

• Design and Synthesis of Novel Amphiphilic Dendritic Galactosides for Selective Targeting of Liposomes to the Hepatic Asialoglycoprotein Receptor
  作者：Leo A. J. M. Sliedregt、Patrick C. N. Rensen、Erik T. Rump、Peter J. van Santbrink、Martin K. Bijsterbosch、A. Rob P. M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom、Theo J. C. van Berkel、Erik A. L. Biessen

  DOI：10.1021/jm981078h

  日期：1999.2.1

  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.