[Pd(byp)CBDCA]

• 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: [Pd(byp)CBDCA]
• 英文别名: [Pd(2,2'-bipyridine)(cyclobutane-1,1-dicarboxylic acid)]；Cyclobutane-1,1-dicarboxylate;palladium(2+);2-pyridin-2-ylpyridine
• 化学式: C₁₆H₁₄N₂O₄Pd
• 分子量: 404.718
• InChiKey: FHHNKVIPVFDZJZ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2,2-联吡啶)二氯钯(II) 、 1,1-环丁基二甲酸 在 silver nitrate 作用下， 以 水 为溶剂， 以93%的产率得到[Pd(byp)CBDCA]
  参考文献：
  名称：

  Kinetics and mechanisms of the ligand substitution reactions of bis(amine)(cyclobutane-1,1-dicarboxylato)palladium(II) †

  摘要：

  关于双齿环丁烷-1,1-二羧酸配体（cbdca）从复合物 [Pd(en)(cbdca)]（en = 乙二胺）和 [Pd(bpy)(cbdca)]（bpy = 2,2'-联吡啶）中位移的动力学和机理研究已经完成。观察到在用硫脲（tu）、四甲基硫脲（tmtu）、肌苷5'-单磷酸（5'-IMP）和碘离子以及酸催化水解反应替代cbdca的过程中，有两个连续的反应步骤。在tu和tmtu取代cbdca后，Pd-结合的含硫亲核试剂的强反向效应导致en配体从 [Pd(en)(cbdca)] 中位移，而对此复合物 [Pd(bpy)(cbdca)] 并未观察到类似的反应。所有的速率和活化参数与联系取代机理相一致。

  DOI：

  10.1039/a804141e

文献信息

• Synthesis, Speciation, DNA Binding, Electrochemical and Antiproliferative Properties of Pd(II) Complexes Designed to Improve the Interaction with DNA
  作者：Haneen AL-Gedany、Azza Shoukry、Saedah Al‐Mhayawi

  DOI：10.21608/ejchem.2021.74711.3679

  日期：2021.7.1

  With the success of cisplatin, extensive research resulted in the discovery of carboplatin (a second-generation drug), where the chloride is replaced by 1,1-cyclobutanedicarboxylate. In the current study, we continue our previous work on the binding behavior of [Pd(byp)(H2O)2]2+ with structural features enhancing the interaction with DNA. [Pd(byp)(gly)]+ (1) and [Pd(byp)(CBDCA)] (2), where byp is 2,2´-bipyridine, gly is glycine, and CBDCA is cyclobutane-1,1´-dicarboxylic acid, were synthesized and characterized. The stability constants and stoichiometries of the complexes formed between various DNA units and [Pd(byp)(H2O)2]2+ were investigated. The binding properties of (1) and (2) with CT-DNA were analyzed by UV-vis spectroscopy, viscosity measurements, and cyclic voltammmetry. The (Kb) value for complex (1) (Kb= 4.36x103 M−1 ) , suggests an electrostatic binding together with hydrogen bonding with the negative sites of CT- DNA. The higher (Kb) value of complex (2) (Kb= 2.11x104 M−1) indicates an intercalation binding mode, whereby a ring-opening reaction of CBDCA occurs, followed by the reaction with guanosine 5'-monophosphate to form [(Pdbyp)(CBDCA-O)(5'-GMP)]. The results from UV-Vis spectroscopy, thermal denaturation, viscosity, and cyclic voltammetry data, all reveal electrostatic binding of complex (1) and intercalation mode of complex (2). The antitumor effects of the two complexes were tested. The two complexes display dose-dependent anti-proliferation activity with a prediction of improved efficacy against cancer

  随着顺铂的成功，大量研究导致了卡铂（第二代药物）的发现，其氯离子被1,1-环丁烷二羧酸根取代。在本研究中，我们继续之前关于[剧(Pd(byp)(H2O)2]2+与增强与DNA相互作用的结构特征的结合行为的工作。合成并表征了[Pd(byp)(gly)]+（1）和[Pd(byp)(CBDCA)]（2），其中byp为2,2'-联吡啶，gly为甘氨酸，CBDCA为环丁烷-1,1'-二羧酸。研究了各种DNA单元与[剧(Pd(byp)( )2]2+形成的复合物的稳定常数和化学计量比。通过紫外可见光谱、粘度测量和循环伏安法分析了(1)和(2)与CT-DNA的结合特性。复合物(1)的结合常数(Kb= 4.36x10³ M⁻¹)表明存在静电结合，并与CT-DNA的负位点形成氢键。复合物(2)的更高Kb值(Kb= 2.11x10⁴ M⁻¹)表明了一种插层结合模式，CBDCA发生开环反应，随后与鸟苷酸5'-单磷酸反应形成[(Pdbyp)(CBDCA-O)(5'-GMP)]。来自紫外可见光谱、热变性、粘度和循环伏安法的数据均揭示了复合物(1)的静电结合和复合物(2)的插层模式。测试了这两种复合物的抗肿瘤效果，两种复合物显示出剂量依赖的抗增殖活性，并预测在抗癌方面具有更好的疗效。
• (2,2′-Bipyridine-κ²<i>N</i>,<i>N</i>′)(1,1-cyclobutanedicarboxylato-κ²<i>O</i>,<i>O</i>′)palladium(II), (1,1-cyclobutanedicarboxylato-κ²<i>O</i>,<i>O</i>′)(1,10-phenanthroline-κ²<i>N</i>,<i>N</i>′)palladium(II) monohydrate and (1,1-cyclobutanedicarboxylato-κ²<i>O</i>,<i>O</i>′)(1,10-phenanthroline-κ²<i>N</i>,<i>N</i>′)palladium(II) dihydrate
  作者：Yasunori Muranishi、Nobuo Okabe

  DOI：10.1107/s0108270103028130

  日期：2004.2.15

  In the three title compounds, [Pd(C6H6O4)(C10H8N2)], (I), [Pd(C6H6O4)(C12H8N2)].H2O, (IIa), and [Pd(C6H6O4)(C12H8N2)].2H(2)O, (IIb), respectively, each Pd-II atom has a similar distorted cis-planar four-coordination geometry, completed by two O atoms of a bidentate 1,1-cyclobutanedicarboxylate anion and two N atoms of either a 2,2'-bipyridine or a 1,10-phenanthroline ligand.