bis(5,7-dimethyl-8-hydroxyquinolinato)copper(II) | 1352406-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: bis(5,7-dimethyl-8-hydroxyquinolinato)copper(II)
• 英文别名: [Cu(5-Me-7-Me-8-HQ)₂]；[Cu(Me₂q)₂]；Copper;5,7-dimethylquinolin-8-olate；copper;5,7-dimethylquinolin-8-olate
• CAS: 1352406-50-8
• 化学式: C₂₂H₂₀CuN₂O₂
• 分子量: 407.959
• InChiKey: NBOHGCBULSZURK-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,7-二甲基-8-羟基喹啉 、 copper(II) choride dihydrate 以 甲醇 、 水 为溶剂， 反应 0.5h， 以76%的产率得到bis(5,7-dimethyl-8-hydroxyquinolinato)copper(II)
  参考文献：
  名称：

  Copper-Dependent Cytotoxicity of 8-Hydroxyquinoline Derivatives Correlates with Their Hydrophobicity and Does Not Require Caspase Activation

  摘要：

  This study reports the structure-activity relationship of a series of 8-hydroxoquinoline derivatives (8-HQs) and focuses on the cytotoxic activity of 5-Cl-7-I-8-HQ (clioquinol, CQ) copper complex (Cu(CQ)). 8-HQs alone cause a dose-dependent loss of viability of the human tumor HeLa and PC3 cells, but the coadministration of copper increases the ligands effects, with extensive cell death occurring in both cell lines. Cytotoxic doses of Cu(CQ) promote intracellular copper accumulation and massive endoplasmic reticulum vacuolization that precede a nonapoptotic (paraptotic) cell death. The cytotoxic effect of Cu(CQ) is reproduced in normal human endothelial cells (HUVEC) at concentrations double those effective in tumor cells, pointing to a potential therapeutic window for Cu(CQ). Finally, the results show that the paraptotic cell death induced by Cu(CQ) does not require nor involve caspases, giving an indication for the current clinical assessment of clioquinol as an antineoplastic agent.

  DOI：

  10.1021/jm301053a

文献信息

• Copper-Dependent Cytotoxicity of 8-Hydroxyquinoline Derivatives Correlates with Their Hydrophobicity and Does Not Require Caspase Activation
  作者：Saverio Tardito、Amelia Barilli、Irene Bassanetti、Matteo Tegoni、Ovidio Bussolati、Renata Franchi-Gazzola、Claudio Mucchino、Luciano Marchiò

  DOI：10.1021/jm301053a

  日期：2012.12.13

  This study reports the structure-activity relationship of a series of 8-hydroxoquinoline derivatives (8-HQs) and focuses on the cytotoxic activity of 5-Cl-7-I-8-HQ (clioquinol, CQ) copper complex (Cu(CQ)). 8-HQs alone cause a dose-dependent loss of viability of the human tumor HeLa and PC3 cells, but the coadministration of copper increases the ligands effects, with extensive cell death occurring in both cell lines. Cytotoxic doses of Cu(CQ) promote intracellular copper accumulation and massive endoplasmic reticulum vacuolization that precede a nonapoptotic (paraptotic) cell death. The cytotoxic effect of Cu(CQ) is reproduced in normal human endothelial cells (HUVEC) at concentrations double those effective in tumor cells, pointing to a potential therapeutic window for Cu(CQ). Finally, the results show that the paraptotic cell death induced by Cu(CQ) does not require nor involve caspases, giving an indication for the current clinical assessment of clioquinol as an antineoplastic agent.