DCM-Lys(ahGalNAc)3 | 1279699-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: DCM-Lys(ahGalNAc)3
• CAS: 1279699-69-2
• 化学式: C₅₂H₉₆N₈O₂₁
• 分子量: 1169.38
• InChiKey: ACVRIOZQBIKDNF-RIFQUYGMSA-N

物化性质

• 沸点：
  1431.3±65.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  81.0
• 可旋转键数：
  40.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  441.31
• 氢给体数：
  16.0
• 氢受体数：
  23.0

反应信息

• 作为产物：
  描述：

  ε-benzyloxycarbonyl-α-dicarboxylmethyl-L-lysine-tris(aminohexyl-β-N-acetylgalactosamine) 在 palladium 10% on activated carbon 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 DCM-Lys(ahGalNAc)3
  参考文献：
  名称：

  NOVEL LIVER-TARGETING AGENTS AND THEIR SYNTHESIS

  摘要：

  该发明提供了新型的肝靶向药物及其合成方法。一种肝靶向药物，以赖氨酸为骨架，具有氨基三乙酸结构，通过与糖苷基团形成多价性，与半乳糖胺链或乳糖链结合。具体来说，仅涉及一种氨基酸L-赖氨酸，以提供三价性。Nε-苄氧羰基-Nα-二羧甲基-L-赖氨酸中的所有羧基可以在一步中与三个ahGalNAc或ahLac的糖苷结合。该发明还提供了一种六乳糖苷。具体来说，TFA-AHA-Asp被用于将2摩尔的NTA(ahLac)3结合。该发明还提供了一种在NTA和DTPA之间添加间隔物的方法。扩展的肝细胞特异性糖基配体的111In标记产率高于非扩展的配体。

  公开号：

  US20110077386A1

文献信息

• New and more efficient multivalent glyco-ligands for asialoglycoprotein receptor of mammalian hepatocytes
  作者：Reiko T. Lee、Mei-Hui Wang、Wuu-Jyh Lin、Yuan C. Lee

  DOI：10.1016/j.bmc.2011.03.027

  日期：2011.4

  New multi-valent, carbohydrate ligands that contain terminal N-acetylgalactosamine (GalNAc) or lactose (Lac) were prepared using a nitrilotriacetic acid (NTA) derivative of L-lysine as scaffold. Tri-valent structures were prepared by attaching an x-amino glycoside of GalNAc or Lac to each of the three carboxyl groups of N-epsilon-protected N-alpha-dicarboxymethyl-L-lysine. In addition, a hexa-valent lactoside was synthesized by attaching N-epsilon-deprotected trivalent lactoside to each of the carboxyl group of N-alpha-(trifluoroacetamido) hexanoyl L-aspartic acid. Tri-valent GalNAc glycosides and the hexa-valent lactoside had high affinity (dissociation constants approaching nM) for rat hepatocytes. The hexa-valent lactoside, after de-Ne-protection, was modified with a chelator, diethylenetriaminepentaacetic acid (DTPA), through which a fluorescent or radioactive tag, such as europium or indium, can be firmly attached. Intravenous infusion of (111)Indium-tagged hexa-valent lactoside to rats and mice resulted in nearly exclusive accumulation of radioactivity in the liver.(C) 2011 Elsevier Ltd. All rights reserved.