α,α-D-trehalose octakis(3,4,5-trihydroxybenzoate) | 1314875-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: α,α-D-trehalose octakis(3,4,5-trihydroxybenzoate)
• 英文别名: Trypanothione synthetase-IN-3；[(2R,3R,4S,5R,6R)-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]-6-[(2R,3R,4S,5R,6R)-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-2-yl]oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 1314875-96-1
• 化学式: C₆₈H₅₄O₄₃
• 分子量: 1559.15
• InChiKey: LVWJZBHMFBYXBN-UUTZMJNCSA-N

物化性质

• 密度：
  2.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  111.0
• 可旋转键数：
  20.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  723.61
• 氢给体数：
  24.0
• 氢受体数：
  43.0

反应信息

• 作为产物：
  描述：

  海藻糖 、 3,4,5-三苄氧基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 四氢呋喃 、 甲醇 为溶剂， 30.0 ℃ 、288.8 kPa 条件下， 以80%的产率得到α,α-D-trehalose octakis(3,4,5-trihydroxybenzoate)
  参考文献：
  名称：

  Galloyl Carbohydrates with Antiangiogenic Activity Mediated by Capillary Morphogenesis Gene 2 (CMG2) Protein Binding

  摘要：

  We previously showed that a small molecule of natural origin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose (PGG), binds to capillary morphogenesis gene 2 (CMG2) with a submicromolar IC50 and also has antiangiogenic activity in vitro and in vivo. In this work, we synthetized derivatives of PGG with different sugar cores and phenolic substituents and tested these as angiogenesis inhibitors. In a high-throughput Forster resonant energy transfer-based binding assay, we found that one of our synthetic analogues (1,2,3,4,6-penta-O-galloyl-beta-D-mannopyranose (PGM)), with mannose as central core and galloyl substituents, exhibit higher (up to 10x) affinity for CMG2 than the natural glucose prototype PGG and proved to be a potent angiogenesis inhibitor. These findings demonstrate that biochemical CMG2 binding in vitro predicts inhibition of endothelial cell migration ex vivo and antiangiogenic activity in vivo. The molecules herein described, and in particular PGM, might be useful prototypes for the development of novel agents for angiogenesis-dependent diseases, including blinding eye disease and cancer.

  DOI：

  10.1021/acs.jmedchem.8b01988