TriMan_insatc24 | 1435941-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: TriMan_insatc24
• 英文别名: N-[1,3-bis[3-oxo-3-[2-[2-[2-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]ethoxy]ethoxy]ethylamino]propoxy]-2-[[3-oxo-3-[2-[2-[2-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethoxy]ethoxy]ethoxy]ethylamino]propoxy]methyl]propan-2-yl]pentacosa-10,12-diynamide
• CAS: 1435941-43-7
• 化学式: C₈₀H₁₄₄N₄O₃₄
• 分子量: 1706.03
• InChiKey: JJOYPZLLTMIIHW-VZUOKGOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  118
• 可旋转键数：
  77
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  525
• 氢给体数：
  16
• 氢受体数：
  34

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到TriMan_insatc24
  参考文献：
  名称：

  Dynamic Micelles of Mannoside Glycolipids are more Efficient than Polymers for Inhibiting HIV-1 trans-Infection

  摘要：

  Mannoside glycolipid conjugates are able to inhibit human immunodeficiency virus type 1 (HIV-1) trans-infection mediated by human dendritic cells (DCs). The conjugates are formed by three building blocks: a linear or branched mannose head, a hydrophilic linker, and a 24-carbon lipid chain. We have shown that, even as single molecules, these compounds efficiently target mannose-binding lectins, such as DC-specific ICAM-3-grabbing nonintegrin (DC-SIGN) important for HIV-1 transmission. With the goal to optimize their inhibitory activity by supramolecular structure formation, we have compared saturated and unsaturated conjugates, as single molecules, self-assemblies of dynamic micelles, and photopolymerized cross-linked polymers. Surface plasmon resonance showed that, unexpectedly, polymers of trivalent conjugates did not display a higher binding affinity for DC-SIGN than single molecules. Interactions on a chip or in solution were independent of calcium; however, binding to DCs was inhibited by a calcium chelator. Moreover, HIV-1 trans-infection was mostly inhibited by dynamic micelles and not by rigid polymers. The inhibition data revealed a clear correlation between the structure and molecular assembly of a conjugate and its biological antiviral activity. We present an interaction model between DC-SIGN and conjugates-either single molecules, micelles, or polymers-that highlights that the most effective interactions by dynamic micelles involve both mannose heads and lipid chains. Our data reveal that trivalent glycolipid conjugates display the highest microbicide potential for HIV prophylaxis, as dynamic micelles conjugates and not as rigid polymers.

  DOI：

  10.1021/bc4000806