[Zn(phen)(dipico)(H₂O)]*H₂O | 911641-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: [Zn(phen)(dipico)(H₂O)]*H₂O
• 英文别名: [Zn(1,10-phenanthroline)(2,6-dipicolinate)(H₂O)]*H₂O；zinc;1,10-phenanthroline;pyridine-2,6-dicarboxylate;dihydrate
• CAS: 911641-96-8
• 化学式: C₁₉H₁₃N₃O₅Zn*H₂O
• 分子量: 446.735
• InChiKey: TYYHWLBXAWIUNV-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -1.06
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,10-菲罗啉 、 吡啶-2,6-二甲酸 、 水 、 zinc(II) chloride 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以72%的产率得到[Zn(phen)(dipico)(H₂O)]*H₂O
  参考文献：
  名称：

  [Zn(phen)(O,N,O)(H2O)] and [Zn(phen)(O,N)(H2O)] with O,N,O is 2,6-dipicolinate and N,O is l-threoninate: synthesis, characterization, and biomedical properties

  摘要：

  Two ternary Zn(II) complexes, with 1,10-phenanthroline (phen) as the main ligand and a carboxylate-containing ligand [dipicolinate (dipico) or l-threoninate (l-Thr)] as the subsidiary ligand, were prepared and characterized by elemental analysis, Fourier transform IR, UV, and fluorescence spectroscopy, X-ray diffraction, molar conductivity, and electrospray ionization mass spectrometry. X-ray structure analysis shows that both [Zn(phen)(dipico)(H2O)]center dot H2O (1) and [Zn(phen)(l-Thr)(H2O)Cl]center dot 2H(2)O (2) have octahedral geometry about the Zn(II) atom. Both complexes can inhibit topoisomerase I, and have better anticancer activity than cisplatin against nasopharyngeal cancer cell lines, HK1 and HONE-1, with concentrations causing 50 % inhibition of cell proliferation (IC50) in the low micromolar range. Complex 2 has the highest therapeutic index for HK1. Both Zn(II) complexes can induce cell death by apoptosis. Changing the subsidiary ligand in the Zn(II) complexes affects the UV-fluorescence spectral properties of the coordinated phen ligand, the binding affinity for some DNA sequences, nucleobase sequence-selective binding, the phase at which cell cycle progression was arrested for treated cancer cells, and their therapeutic index.

  DOI：

  10.1007/s00775-012-0923-y