bis(2,9-dimethyl-4,7-bis(sulfonatophenyl)-1,10-phenanthrolinato)copper(I)(3-) | 88376-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: bis(2,9-dimethyl-4,7-bis(sulfonatophenyl)-1,10-phenanthrolinato)copper(I)(3-)
• 英文别名: [Cu(2,9-dimethyl-4,7-bis(4'-sulfonatophenyl)-1,10-phenanthroline)2](3-)；Cu(bathocuproine disulfonate)2(3-)；Cu(bcs)2(3-)
• CAS: 88376-66-3
• 化学式: C₅₂H₃₆CuN₄O₁₂S₄
• 分子量: 1100.69
• InChiKey: AZWZUGYVDNHLKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  、 bis(2,9-dimethyl-4,7-bis(sulfonatophenyl)-1,10-phenanthrolinato)copper(I)(3-) 以>99的产率得到
  参考文献：
  名称：

  Allan, Anne E.; Graham Lappin; Laranjeira, Mauro C. M., Inorganic Chemistry, 1984, vol. 23, # 4, p. 477 - 482

  摘要：

  DOI：
• 作为产物：
  描述：

  [Cu(II)(2,9-dimethyl-4,7-bis((sulfonyloxy)phenyl)-1,10-phenanthroline)2](2-) 在 对苯二酚 作用下， 以 further solvent(s) 为溶剂， 生成 bis(2,9-dimethyl-4,7-bis(sulfonatophenyl)-1,10-phenanthrolinato)copper(I)(3-)
  参考文献：
  名称：

  Holwerda, Robert A., Inorganic Chemistry, 1982, vol. 21, # 5, p. 2107 - 2109

  摘要：

  DOI：

文献信息

• Al-Shatti, Najat; Lappin, A. Graham; Sykes, A. Geoffrey, Inorganic Chemistry, 1981, vol. 20, # 5, p. 1466 - 1469
  作者：Al-Shatti, Najat、Lappin, A. Graham、Sykes, A. Geoffrey

  DOI：——

  日期：——
• Hepatocyte Targeting and Intracellular Copper Chelation by a Thiol-Containing Glycocyclopeptide
  作者：Anaïs M. Pujol、Martine Cuillel、Olivier Renaudet、Colette Lebrun、Peggy Charbonnier、Doris Cassio、Christelle Gateau、Pascal Dumy、Elisabeth Mintz、Pascale Delangle

  DOI：10.1021/ja106206z

  日期：2011.1.19

  Metal overload plays an important role in several diseases or intoxications, like in Wilson's disease, a major genetic disorder of copper metabolism in humans. To efficiently and selectively decrease copper concentration in the liver that is highly damaged, chelators should be targeted at the hepatocytes. In the present work, we synthesized a molecule able to both lower intracellular copper, namely Cu(I), and target hepatocytes, combining within the same structure a chelating unit and a carbohydrate recognition element. A cyclodecapeptide scaffold displaying a controlled conformation with two independent faces was chosen to introduce both units. One face displays a cluster of carbohydrates to ensure an efficient recognition of the asialoglycoprotein receptors, expressed on the surface of hepatocytes. The second face is devoted to metal ion complexation thanks to the thiolate functions of two cysteine side-chains. To obtain a chelator that is active only once inside the cells, the two thiol functions were oxidized in a disulfide bridge to afford the glycopeptide P-3. Two simple cyclodecapeptides modeling the reduced and complexing form of P-3 in cells proved a high affinity for Cu(I) and a high selectivity with respect to Zn(II). As expected, P-3 becomes an efficient Cu(I) chelator in the presence of glutathione that mimics the intracellular reducing environment. Finally, cellular uptake and ability to lower intracellular copper were demonstrated in hepatic cell lines, in particular in WIF-B9, making P-3 a good candidate to fight copper overload in the liver.