2'-(3'',4''-methylene-dioxyphenyl)imidazo[4',5'-f][1,10]phenanthroline | 1084866-04-5

• 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: 2'-(3'',4''-methylene-dioxyphenyl)imidazo[4',5'-f][1,10]phenanthroline
• 英文别名: 2-(1,3-benzodioxol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1084866-04-5
• 化学式: C₂₀H₁₂N₄O₂
• 分子量: 340.341
• InChiKey: DQNWXWYXQHXJNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-[Ru(4,7-dimethyl-1,10-phenanthroline)₂Cl₂] 、 2'-(3'',4''-methylene-dioxyphenyl)imidazo[4',5'-f][1,10]phenanthroline 以 乙二醇 为溶剂， 以87%的产率得到[Ru(4,7-dimethyl-1,10-phenanthroline)2(2'-(3'',4''-methylene-dioxyphenyl)imidazol[4',5'-f][1,10]phenanthroline)](ClO4)2*2H2O
  参考文献：
  名称：

  Experimental and density functional theory (DFT) studies on the DNA-binding trend and spectral properties of two new Ru(II) complexes: [Ru(L)2(mip)](ClO4)2 (L=2,9-dmp and 4,7-dmp)

  摘要：

  The new ligand 2'-(3 '',4 ''-methylene-dioxyphenyl)imidazo[4',5'-f] [1,10] phenanthroline (mip) and its Ru(II) complexes [Ru(2,9-dmp)(2)(mip)](2+) (1) (2,9-dmp = 2,9-dimethyl-1,10-phenanthrolline) and [Ru(4,7-dmp)(2)(mip)](2+) (2) (4,7-dmp = 4,7-dimethyl-1,10-phenanthrolline) were synthesized and characterized. The binding properties of the two complexes to calf-thymus DNA (CT-DNA) were investigated by different spectrophotometric methods and viscosity measurements. Both 1 and 2 bind to CT-DNA in an intercalative mode, but with different binding strengths. Complex 2 can emit luminescence in the Tris buffer at ambient temperature, however, complex 1 showed no fluorescence emission, neither alone nor in the presence of CT-DNA. The circular-dichroism signal of the dialysate of the racemic complex against CT-DNA suggests that complexes 1 and 2 interact enantioselectively with CT-DNA. Furthermore, complexes 1 and 2 have been found to be an efficient photosensitiser for cracking DNA plasmid. Theoretical calculations for 1 and 2 were also carried out applying the density functional theory (DFT) method and applied to explain some obtained experimental observations. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.07.033
• 作为产物：
  描述：

  胡椒醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 2.0h， 生成 2'-(3'',4''-methylene-dioxyphenyl)imidazo[4',5'-f][1,10]phenanthroline
  参考文献：
  名称：

  一种钌（II）配合物及其在抗骨肉瘤药物中的应用

  摘要：

  本发明涉及生物技术领域，具体公开了一种钌(II)配合物及其在抗骨肉瘤药物中的应用。钌(II)配合物的化学式为Ru(dmp)2(AAdpip)](ClO4)2，其中Ru(dmp)2(AAdpip)](ClO4)2的结构式为式(I)所示。本发明的钌(II)配合物对骨肉瘤细胞具有抑制增殖作用，呈剂量‑时间依赖效应；钌(II)配合物引起骨肉瘤细胞活性氧增加，钌(II)配合物通过线粒体引起内源性凋亡通路引起骨肉瘤细胞凋亡。不同浓度的钌(Ⅱ)配合物处理骨肉瘤细胞，细胞中染色质凝聚皱缩，着色不规则，细胞核会呈致密浓染，或呈碎块状，呈现细胞凋亡皱缩核碎裂等典型变化。

  公开号：

  CN113549114A

文献信息

• 一种钌（II）配合物及其在抗骨肉瘤药物中的应用
  申请人：广州市第一人民医院（广州消化疾病中心、广州医科大学附属市一人民医院、华南理工大学附属

  公开号：CN113549114A

  公开（公告）日：2021-10-26

  本发明涉及生物技术领域，具体公开了一种钌(II)配合物及其在抗骨肉瘤药物中的应用。钌(II)配合物的化学式为Ru(dmp)2(AAdpip)](ClO4)2，其中Ru(dmp)2(AAdpip)](ClO4)2的结构式为式(I)所示。本发明的钌(II)配合物对骨肉瘤细胞具有抑制增殖作用，呈剂量‑时间依赖效应；钌(II)配合物引起骨肉瘤细胞活性氧增加，钌(II)配合物通过线粒体引起内源性凋亡通路引起骨肉瘤细胞凋亡。不同浓度的钌(Ⅱ)配合物处理骨肉瘤细胞，细胞中染色质凝聚皱缩，着色不规则，细胞核会呈致密浓染，或呈碎块状，呈现细胞凋亡皱缩核碎裂等典型变化。
• Binding properties of Ru(II) polypyridyl complexes with poly(U)·poly(A)*poly(U) triplex: the ancillary ligand effect on third-strand stabilization
  作者：Li-Feng Tan、Ling-Jun Xie、Xiao-Nan Sun

  DOI：10.1007/s00775-012-0950-8

  日期：2013.1

  The binding properties of [RuL2(mip)](2+) where L is 1,10-phenanthroline (phen) or 4,7-dimethyl-1,10-phenanthrollne (4,7-dmp) and mip is 2'-(3aEuro(3),4aEuro(3)-methylenedioxyphenyl)imidazo[4',5'-f][1,10]phenanthroline} with regard to the triplex RNA poly(U)center dot poly(A)*poly(U) were investigated using various biophysical techniques and quantum chemistry calculations. In comparison with [Ru(4,7-dmp)(2)(mip)](2+), remarkably higher binding affinity of [Ru(phen)(2)(mip)](2+) for the triplex RNA poly(U)center dot poly(A)*poly(U) was achieved by changing the ancillary ligands. The stabilization of the Hoogsteen-base-paired third strand was improved by about 10.9 A degrees C by [Ru(phen)(2)(mip)](2+) against 6.6 A degrees C by [Ru(4,7-dmp)(2)(mip)](2+). To the best of our knowledge, [Ru(phen)(2)(mip)](2+) is the first metal complex able to raise the third-strand stabilization of poly(U)center dot poly(A)*poly(U) from 37.5 to 48.4 A degrees C. The results reveal that the ancillary ligands have an important effect on third-strand stabilization of the triplex RNA poly(U)center dot poly(A)*poly(U) when metal complexes contain the same intercalative ligands.
• Experimental and density functional theory (DFT) studies on the DNA-binding trend and spectral properties of two new Ru(II) complexes: [Ru(L)2(mip)](ClO4)2 (L=2,9-dmp and 4,7-dmp)
  作者：Lifeng Tan、Sheng Zhang、Xiaohua Liu、Yuandao Chen、Xuewen Liu

  DOI：10.1016/j.jorganchem.2008.07.033

  日期：2008.10

  The new ligand 2'-(3 '',4 ''-methylene-dioxyphenyl)imidazo[4',5'-f] [1,10] phenanthroline (mip) and its Ru(II) complexes [Ru(2,9-dmp)(2)(mip)](2+) (1) (2,9-dmp = 2,9-dimethyl-1,10-phenanthrolline) and [Ru(4,7-dmp)(2)(mip)](2+) (2) (4,7-dmp = 4,7-dimethyl-1,10-phenanthrolline) were synthesized and characterized. The binding properties of the two complexes to calf-thymus DNA (CT-DNA) were investigated by different spectrophotometric methods and viscosity measurements. Both 1 and 2 bind to CT-DNA in an intercalative mode, but with different binding strengths. Complex 2 can emit luminescence in the Tris buffer at ambient temperature, however, complex 1 showed no fluorescence emission, neither alone nor in the presence of CT-DNA. The circular-dichroism signal of the dialysate of the racemic complex against CT-DNA suggests that complexes 1 and 2 interact enantioselectively with CT-DNA. Furthermore, complexes 1 and 2 have been found to be an efficient photosensitiser for cracking DNA plasmid. Theoretical calculations for 1 and 2 were also carried out applying the density functional theory (DFT) method and applied to explain some obtained experimental observations. (C) 2008 Elsevier B.V. All rights reserved.