2-(2,4-dinitrophenyl)imidazo[4,5-f]1,10-phenanthroline | 1314041-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2,4-dinitrophenyl)imidazo[4,5-f]1,10-phenanthroline
• 英文别名: 2-(2,4-dinitrophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1314041-42-3
• 化学式: C₁₉H₁₀N₆O₄
• 分子量: 386.326
• InChiKey: XZIZPWWUNCXFAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-[Ru(dmp)₂Cl₂]*2H₂O 、 2-(2,4-dinitrophenyl)imidazo[4,5-f]1,10-phenanthroline 、 sodium perchlorate 以 水 、 乙二醇 为溶剂， 以71%的产率得到bis(2,9-dimethyl-1,10-phenanthroline)(2-(2,4-dinitrophenyl)imidazo[4,5-f][1,10]phenanthroline)ruthenium(II) perchlorate
  参考文献：
  名称：

  Ruthenium(II) complexes: Cellular uptake, cytotoxicity, DNA-binding, photocleavage and antioxidant activity studies

  摘要：

  Two new ruthenium(II) complexes [Ru(dmp)(2)(DNPIP)](2+) 1 and [Ru(dmp)(2)(DAPIP)](2+) 2 were synthesized and characterized. The DNA-binding behaviors of these complexes were investigated by absorption spectra, viscosity measurements and photocleavage. The DNA-binding constants for complexes 1 and 2 have been determined to be 6.24 (+/-0.11) x 10(4) and 1.64 (+/-0.49) x 10(4) M-1. The results suggest that complexes 1 and 2 intercalate between the DNA base pairs. Binding stoichiometries were studied through a luminescence-based Job plot. The major inflection points for complexes 1 and 2 at chi = 0.31 and chi = 0.51 were observed. The data were consistent with 2:1 and 1:1 bp [complex]/[DNA] binding mode. Complex 1 shows higher activity than complex 2 against the selected tumor cell lines. In addition, the cellular uptake and antioxidant activity on hydroxyl radical were also explored. Crown Copyright (C) 2011 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.011
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 2,4-二硝基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以69%的产率得到2-(2,4-dinitrophenyl)imidazo[4,5-f]1,10-phenanthroline
  参考文献：
  名称：

  Photo-induced mitochondrial DNA damage and NADH depletion by –NO₂ modified Ru(ii) complexes

  摘要：

  首次报道了具有同步光催化NADH耗竭能力的Ru（ii）PACT代理，并在一光子和二光子激发下对顺铂耐药癌细胞显示出良好的活性。

  DOI：

  10.1039/d1cc00258a

文献信息

• Synthesis, cellular uptake, apopotosis, cytotoxicity, cell cycle arrest, interaction with DNA and antioxidant activity of ruthenium(II) complexes
  作者：Hong-Liang Huang、Zheng-Zheng Li、Zhen-Hua Liang、Jun-Hua Yao、Yun-Jun Liu

  DOI：10.1016/j.ejmech.2011.04.049

  日期：2011.8

  A new ligand and two ruthenium(II) complexes [Ru(bpy)2(DNPIP)](ClO4)2 1 and [Ru(bpy)2(DAPIP)](ClO4)2 2 were synthesized and characterized. The DNA-binding constants for complexes 1 and 2 were determined to be 2.24 (±0.30) × 105 M−1 (s = 1.29) and 6.34 (±0.32) × 104 M−1 (s = 2.84). The photocleavage of pBR322 DNA by Ru(II) complexes was investigated. The cytotoxicity of complexes 1 and 2 were assessed

  合成并表征了一种新的配体和两种钌（II）络合物[Ru（bpy）2（DNPIP）]（ClO 4）2 1和[Ru（bpy）2（DAPIP）]（ClO 4）2 2。测定复合物1和2的DNA结合常数为2.24（±0.30）×10 5  M -1（s  ＝ 1.29）和6.34（±0.32）×10 4  M -1（s  ＝ 2.84）。研究了Ru（II）配合物对pBR322 DNA的光裂解作用。配合物1和2的细胞毒性针对三种肿瘤细胞系进行了评估。研究了细胞凋亡和细胞摄取。探索了pGL 3质粒DNA的阻滞测定。通过流式细胞术分析细胞周期停滞。还研究了配体和配合物的抗氧化活性。
• Cytotoxicity, apoptosis, interaction with DNA, cellular uptake, and cell cycle arrest of ruthenium(II) polypyridyl complexes containing 4,4′-dimethyl-2,2′-bipyridine as ancillary ligand
  作者：Hong-Liang Huang、Zheng-Zheng Li、Xiu-Zhen Wang、Zhen-Hua Liang、Yun-Jun Liu

  DOI：10.1080/00958972.2012.713945

  日期：2012.9.20

  is more active than 2 against selected cancer cell lines. The apoptosis induced by these complexes was studied. Cellular uptake showed that these complexes could enter into the cytoplasm and accumulate in the nuclei. The cell cycle arrest and antioxidant activity against hydroxyl radicals were also investigated.

  两种新的钌 (II) 多吡啶配合物，[Ru(dmb)2(DNPIP)](ClO4)2 (1) (DNPIP = 2-(2,4-二硝基苯基)咪唑并[4,5-f][1,10 ]菲咯啉，dmb = 4,4'-二甲基-2,2'-联吡啶）和 [Ru(dmb)2(DAPIP)](ClO4)2 (2) (DAPIP = 2-(2,4-diaminophenyl)imidazo [4,5f][1,10] 菲咯啉），被合成和表征。这些复合物的 DNA 结合行为已通过 UV-Vis 吸收滴定、粘度测量和光裂解进行了研究。1 和 2 的 DNA 结合常数分别为 7.39 (±0.16) × 104 (s = 2.68) 和 2.73 (±0.16) × 104 (mol L−1)−1 (s = 0.64)。研究了它们作为对不同癌细胞系的细胞毒性剂的评估，针对 BEL-7402、HepG-2 的 IC50 值为 59
• Ruthenium(II) complexes: Cellular uptake, cytotoxicity, DNA-binding, photocleavage and antioxidant activity studies
  作者：Zheng-Zheng Li、Zhen-Hua Liang、Hong-Liang Huang、Yun-Jun Liu

  DOI：10.1016/j.molstruc.2011.06.011

  日期：2011.8

  Two new ruthenium(II) complexes [Ru(dmp)(2)(DNPIP)](2+) 1 and [Ru(dmp)(2)(DAPIP)](2+) 2 were synthesized and characterized. The DNA-binding behaviors of these complexes were investigated by absorption spectra, viscosity measurements and photocleavage. The DNA-binding constants for complexes 1 and 2 have been determined to be 6.24 (+/-0.11) x 10(4) and 1.64 (+/-0.49) x 10(4) M-1. The results suggest that complexes 1 and 2 intercalate between the DNA base pairs. Binding stoichiometries were studied through a luminescence-based Job plot. The major inflection points for complexes 1 and 2 at chi = 0.31 and chi = 0.51 were observed. The data were consistent with 2:1 and 1:1 bp [complex]/[DNA] binding mode. Complex 1 shows higher activity than complex 2 against the selected tumor cell lines. In addition, the cellular uptake and antioxidant activity on hydroxyl radical were also explored. Crown Copyright (C) 2011 Published by Elsevier B.V. All rights reserved.
• Photo-induced mitochondrial DNA damage and NADH depletion by –NO₂ modified Ru(<scp>ii</scp>) complexes
  作者：Shuang Qi、Zhihui Jin、Yao Jian、Yuanjun Hou、Chao Li、Yao Zhao、Xuesong Wang、Qianxiong Zhou

  DOI：10.1039/d1cc00258a

  日期：——

  Ru(ii) PACT agents with a synchronous photo-catalyzed NADH depletion ability were reported for the first time and displayed good activity towards cisplatin-resistant cancer cells upon one- and two-photon excitation.

  首次报道了具有同步光催化NADH耗竭能力的Ru（ii）PACT代理，并在一光子和二光子激发下对顺铂耐药癌细胞显示出良好的活性。