β-D-maltose octakis(3,4,5-trihydroxybenzoate) | 1314875-95-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: β-D-maltose octakis(3,4,5-trihydroxybenzoate)
• 英文别名: galloyl(-2)[galloyl(-3)][galloyl(-4)][galloyl(-6)]Glc(a1-4)[galloyl(-2)][galloyl(-3)][galloyl(-6)]Glc(b)-O-galloyl；[(2R,3R,4S,5R,6S)-4,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]-3-[(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: 1314875-95-0
• 化学式: C₆₈H₅₄O₄₃
• 分子量: 1559.15
• InChiKey: MHDRUWNQMFMBPA-MLDWKAQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  111
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  724
• 氢给体数：
  24
• 氢受体数：
  43

反应信息

• 作为产物：
  描述：

  麦芽糖 、 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82%的产率得到β-D-maltose 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

文献信息

• [EN] GP120 -BINDING BENZENE COMPOUNDS AND SACCHARIDE COMPOUNDS<br/>[FR] COMPOSÉS DE BENZÈNES ET DE SACCHARIDES SE LIANT À GP120
  申请人：UNIV LEUVEN KATH

  公开号：WO2011085454A1

  公开（公告）日：2011-07-21

  The present invention provides for novel benzene compounds and saccharide compounds and for the use of said compounds for binding, titration (quantification), removing, purifying or separating the glycoprotein gp120, gp120 comprising viruses or cells infected with gp120 comprising viruses. The invention also provides for a method for the detection, binding, titration (quantification), removal, purification or separation of (or directing therapeutic or other agents to) gp120, gp120 comprising viruses or cells infected with gp120 comprising viruses. The invention further provides for the use of the compounds and for methods using the compounds for directing anti -viral drugs or other agents to gp120 comprising viruses or to gp120 comprising virus - infected cells. The present invention also provides processes for the preparation of said novel compounds.

  本发明提供了新型苯化合物和糖化合物，并用于结合、滴定（定量）、去除、纯化或分离含有糖蛋白gp120的化合物的用途，该gp120包括病毒或感染有包含gp120病毒的细胞。本发明还提供了一种用于检测、结合、滴定（定量）、去除、纯化或分离（或将治疗或其他药物引导至）gp120的方法，该gp120包括病毒或感染有包含gp120病毒的细胞。本发明进一步提供了利用这些化合物的用途，以及用于将抗病毒药物或其他药物引导至含有gp120的病毒或含有gp120病毒感染细胞的方法。本发明还提供了用于制备这些新型化合物的工艺。