4'-(1H-imidazol-2-yl)-2,2':,6',2''-terpyridine | 873927-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4'-(1H-imidazol-2-yl)-2,2':,6',2''-terpyridine
• 英文别名: 4'-(1H-imidazol-2-yl)-2,2':6',2''-terpyridine；4'-(imidazole)-2,2':6,2''-terpyridine；imidazole terpyridine；imidazolylterpyridine；Itpy；4-(1H-imidazol-2-yl)-2,6-dipyridin-2-ylpyridine
• CAS: 873927-64-1
• 化学式: C₁₈H₁₃N₅
• 分子量: 299.335
• InChiKey: BHRQXEHDJGOXNM-UHFFFAOYSA-N

物化性质

• 沸点：
  603.7±55.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(1H-imidazol-2-yl)-2,2':,6',2''-terpyridine 在 H₂O₂ 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 生成 [Co(imidazole-terpyridine(+1H))2](ClO4)5*5H2O
  参考文献：
  名称：

  Cobalt complexes of terpyridine ligands: Crystal structure and nuclease activity

  摘要：

  Cobalt(II) (1) and cobalt(III) (2) complexes of tridentate ligand. imidazole terpyridine (Itpy), have been synthesized and characterized by both spectroscopic and electrochemical techniques. Single crystal X-ray diffraction studies of complexes 1 and 2 shows that the complexes belong to monoclinic crystal system, with the two Itpy ligands coordinated to the central metal ion. The binding behavior of both the cobalt complexes to Calf thymus DNA has been investigated by UV-Vis, fluorescence Spectroscopy, viscosity and electrochemical measurements. The results Suggest that complexes 1 and 2 bind to DNA through intercalation. The intrinsic DNA binding constant values Obtained from absorption Spectral titration studies were found to be (5.07 +/- 0.12) x 10(3) M-1 and (7.46 +/- 0.16) > 10(3) M-1, respectively, for complexes 1 and 2. Gel electrophoresis Studies with the cobalt complexes show that while complex 1 cleaves DNA in the presence of hydrogen peroxide, complex 2 cleaves DNA in the presence of ascorbic acid and hydrogen peroxide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2008.08.003
• 作为产物：
  描述：

  2-乙酰基吡啶 、 2-咪唑甲醛 在 ammonium acetate 、 溶剂黄146 、 sodium hydroxide 作用下， 反应 2.0h， 生成 4'-(1H-imidazol-2-yl)-2,2':,6',2''-terpyridine
  参考文献：
  名称：

  DNA/protein interaction and cytotoxic activity of imidazole terpyridine derived Cu(ii)/Zn(ii) metal complexes

  摘要：

  我们合成并表征了两种基于咪唑三吡啶（itey）的配合物，[Cu(itey)(OAc)(H2O)]NO3-H2O（1）和[Zn(itey)(OAc)]OAc（2）。复合物 1 的晶体结构显示出具有反平行堆积排列的扭曲八面体几何结构。利用吸收滴定法和圆二色性研究了这两种复合物与小牛胸腺 DNA（ctDNA）的相互作用。复合物 1 显示出与 DNA 碱基的配位结合，而复合物 2 则显示出与 DNA 的插层结合模式。由于存在氧化还原活性铜（II）中心，复合物 1 在添加剂存在的情况下会通过氧化途径裂解 DNA。然而，复合物 2 会水解 DNA。利用荧光淬灭和圆二色性实验研究了这两种复合物与牛血清白蛋白的相互作用。圆二色性分析表明，这两种复合物都会对蛋白质的二级结构产生强烈影响。荧光淬灭实验表明，复合物 1 和 2 在蛋白质上有不同的结合位点。此外，复合物对 A549 肺癌细胞系具有潜在的细胞毒性。两种复合物都能诱导细胞凋亡。

  DOI：

  10.1039/c4dt01378f

文献信息

• Ruthenium(ii) [3 + 2 + 1] mixed ligand complexes: substituent effect on photolability, photooxidation of bases, photocytotoxicity and photonuclease activity
  作者：Gopal Sathyaraj、Mathiyalagan Kiruthika、Thomas Weyhermüller、Balachandran Unni Nair

  DOI：10.1039/c2dt30260h

  日期：——

  Mixed ligand complexes of ruthenium(II), [Ru(itpy)(bpy)Cl]ClO41, [Ru(itpy)(phen)Cl]ClO42, [Ru(bitpy)(bpy)Cl]ClO43 and [Ru(bitpy)(phen)Cl]ClO44 have been synthesized and characterized. Complex 3 has also been characterized crystallographically. These complexes exhibit photolability of the Ru–Cl bond. Upon irradiation at 440 nm in the presence of nucleosides and nucleotides the complexes exchange chloride for the nucleoside or nucleotide. The photolability of the Ru–Cl bond depends on the nature of the substituent in the tridentate tpy ligand. Photolysis of the complexes in the presence of a nucleoside or nucleotide also produces 8-oxoguanine due to the oxidation of guanine by the excited states of the complexes. These four complexes exhibit photonuclease properties and bring about the cleavage of plasmid DNA when irradiated at 440 nm. These complexes have been found to be toxic towards NIH 3T3 cells under photolytic conditions.

  已经合成并表征了二价钌的混合配体络合物[Ru(itpy)(bpy)Cl]ClO4、[Ru(itpy)(phen)Cl]ClO4、[Ru(bitpy)(bpy)Cl]ClO4和[Ru(bitpy)(phen)Cl]ClO4。复合物3也进行了晶体学表征。这些复合物表现出Ru–Cl键的光解特性。在440 nm光照下，在核苷和核苷酸存在的情况下，复合物与核苷或核苷酸交换氯离子。Ru–Cl键的光解性依赖于三齿tpy配体中取代基的性质。在核苷或核苷酸的存在下，这些复合物的光分解还会产生8-氧鸟苷，这是由于复合物的激发态对鸟苷的氧化。这四个复合物表现出光核酸酶特性，在440 nm光照下能够切割质粒DNA。这些复合物在光解条件下对NIH 3T3细胞表现出毒性。
• A new platinum(<scp>ii</scp>) complex for bioimaging applications
  作者：Verasundaram M. Manikandamathavan、Natarajan Duraipandy、Manikantan S. Kiran、Vaidyanathan G. Vaidyanathan、Balachandran U. Nair

  DOI：10.1039/c5ra00002e

  日期：——

  A new Pt(ii) complex bearing terpyridine derivative exhibit specificity towards nuclear DNA. The staining ability has been explored in cell imaging as well as in gel electrophoresis an alternative to highly mutagenic ethidium bromide.

  一种带有三吡啶衍生物的新型 Pt (II) 配合物表现出对核DNA的特异性。该染色能力已经在细胞成像和凝胶电泳中得到探索，作为高度致突变性溴乙酸乙酯的替代品。
• Copper(II) Terpyridine Complexes: Effect of Substituent on DNA Binding and Nuclease Activity
  作者：Varadarajan Uma、Munusamy Elango、Balachandran Unni Nair

  DOI：10.1002/ejic.200700053

  日期：2007.8

  Mononuclear copper(II) terpyridine complexes, [Cu(ttpy)Cl]Cl (1) and [Cu(itpy)Cl]Cl (2) (ttpy = tolylterpyridine and itpy = imidazolylterpyridine) were synthesized and characterized. The interaction of the complexes with DNA was studied by electronic and CD spectroscopy, viscosity and gel electrophoresis. Absorption titrations, viscosity and CD experiments reveal an intercalative mode of DNA binding for these

  合成并表征了单核铜 (II) 三联吡啶配合物 [Cu(ttpy)Cl]Cl (1) 和 [Cu(itpy)Cl]Cl (2)（ttpy = 甲苯基三联吡啶和 itpy = 咪唑基三联吡啶）。通过电子和 CD 光谱、粘度和凝胶电泳研究复合物与 DNA 的相互作用。吸收滴定、粘度和 CD 实验揭示了这些复合物的 DNA 结合的嵌入模式。1 和 2 的结合常数值分别为 (5.6 ± 0.2) × 104 和 (1.4 ± 0.2) × 104M–1，表明这些复合物与 DNA 的结合程度适中。从计算研究中发现，在甲苯基三联吡啶（复合物 1）的情况下，芳香 π 云分布更均匀，这可能导致与 DNA 碱基更好的堆叠相互作用，因此复合物 1 的结合常数值更高。
• DNA/protein interaction and cytotoxic activity of imidazole terpyridine derived Cu(<scp>ii</scp>)/Zn(<scp>ii</scp>) metal complexes
  作者：V. M. Manikandamathavan、T. Weyhermüller、R. P. Parameswari、M. Sathishkumar、V. Subramanian、Balachandran Unni Nair

  DOI：10.1039/c4dt01378f

  日期：——

  Two imidazole terpyridine (itpy) based complexes, [Cu(itpy)(OAc)(H2O)]NO3·H2O (1) and [Zn(itpy)(OAc)]OAc (2) have been synthesised and characterized. The crystal structure of complex 1 shows distorted octahedral geometry with an anti-parallel stacking arrangement. The interactions of the two complexes with Calf thymus DNA (ctDNA) have been studied using absorption titration and circular dichroism. Complex 1 shows coordinate binding to DNA bases, and complex 2 shows an intercalative mode of binding with DNA. Complex 1 cleaves the DNA via an oxidative pathway in the presence of additives, because of the presence of a redox active copper(II) centre. However, complex 2 cleaves DNA hydrolytically. Interactions of the two complexes with bovine serum albumin have been studied using fluorescence quenching and circular dichroism experiments. Circular dichroic analysis reveals that both the complexes strongly influence the secondary structure of the protein. Fluorescence quenching experiments indicate that there are different binding sites for complexes 1 and 2 on the protein. Furthermore, the complexes show potential cytotoxicity towards the A549 lung cancer cell line. Both the complexes have been found to induce apoptosis.

  我们合成并表征了两种基于咪唑三吡啶（itey）的配合物，[Cu(itey)(OAc)(H2O)]NO3-H2O（1）和[Zn(itey)(OAc)]OAc（2）。复合物 1 的晶体结构显示出具有反平行堆积排列的扭曲八面体几何结构。利用吸收滴定法和圆二色性研究了这两种复合物与小牛胸腺 DNA（ctDNA）的相互作用。复合物 1 显示出与 DNA 碱基的配位结合，而复合物 2 则显示出与 DNA 的插层结合模式。由于存在氧化还原活性铜（II）中心，复合物 1 在添加剂存在的情况下会通过氧化途径裂解 DNA。然而，复合物 2 会水解 DNA。利用荧光淬灭和圆二色性实验研究了这两种复合物与牛血清白蛋白的相互作用。圆二色性分析表明，这两种复合物都会对蛋白质的二级结构产生强烈影响。荧光淬灭实验表明，复合物 1 和 2 在蛋白质上有不同的结合位点。此外，复合物对 A549 肺癌细胞系具有潜在的细胞毒性。两种复合物都能诱导细胞凋亡。
• Cobalt complexes of terpyridine ligands: Crystal structure and nuclease activity
  作者：Ramasamy Indumathy、Mookandi Kanthimathi、T. Weyhermuller、Balachandran Unni Nair

  DOI：10.1016/j.poly.2008.08.003

  日期：2008.11

  Cobalt(II) (1) and cobalt(III) (2) complexes of tridentate ligand. imidazole terpyridine (Itpy), have been synthesized and characterized by both spectroscopic and electrochemical techniques. Single crystal X-ray diffraction studies of complexes 1 and 2 shows that the complexes belong to monoclinic crystal system, with the two Itpy ligands coordinated to the central metal ion. The binding behavior of both the cobalt complexes to Calf thymus DNA has been investigated by UV-Vis, fluorescence Spectroscopy, viscosity and electrochemical measurements. The results Suggest that complexes 1 and 2 bind to DNA through intercalation. The intrinsic DNA binding constant values Obtained from absorption Spectral titration studies were found to be (5.07 +/- 0.12) x 10(3) M-1 and (7.46 +/- 0.16) > 10(3) M-1, respectively, for complexes 1 and 2. Gel electrophoresis Studies with the cobalt complexes show that while complex 1 cleaves DNA in the presence of hydrogen peroxide, complex 2 cleaves DNA in the presence of ascorbic acid and hydrogen peroxide. (C) 2008 Elsevier Ltd. All rights reserved.