bis(1,2-dimethyl-3-hydroxy-4-pyridinonato)copper (II) | 150118-16-4

• 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: bis(1,2-dimethyl-3-hydroxy-4-pyridinonato)copper (II)
• 英文别名: bis(1,2-dimethyl-3-hydroxy-4-pyridinonato)copper(II)；Cu(dmpp)₂
• CAS: 150118-16-4
• 化学式: C₁₄H₁₆CuN₂O₄
• 分子量: 339.838
• InChiKey: UHTBYVDBOXMRGC-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  1,2-二甲基-3-羟基-4-吡啶酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 bis(1,2-dimethyl-3-hydroxy-4-pyridinonato)copper (II)
  参考文献：
  名称：

  Uncovering novel 3-hydroxy-4-pyridinone metal ion complexes with potential anti-inflammatory properties

  摘要：

  Ligands of the 3-hydroxy-4-pyridinone (3,4-HPO) type, with one (Hmpp) or two methyl groups (Hdmpp), have been reported to possess biomedical, chemical and analytical applications. In this first screening study aiming to uncover new promising agents to mitigate the oxidative damage highly present in several metabolic disorders, such as diabetes mellitus, we assessed the potential of twelve 3,4-HPO metal ion complexes to modulate oxidative burst in human neutrophils. Metal ion 3,4-HPO complexes of Ni, Fe, V, Co, Cu and Zn were synthesized and tested up to 15 mu M. Among all the compounds, [Cu(mpp)(2)] and [Cu(dmpp)(2)] exhibited the highest scavenging capacity against superoxide radical (O-2(center dot-)) (IC50 = 0.36 +/- 0.07 and 0.30 +/- 0.06 M, respectively) and against hypochlorous acid (HOCl) (IC50 = 0.6 +/- 0.3 and 0.4 +/- 0.1 mu M, respectively). In the particular case of O-2(center dot-), [Fe(mpp)(3)] and [Fe(dmpp)(3)] (both at 15 mu M) presented 35% and 22% of inhibition, respectively, while all the other compounds were neither able to scavenge O-2(center dot-) nor stimulate its production. Regarding the scavenging capacity against hydrogen peroxide (H2O2), all the compounds showed low efficiency (from 6-39%). Finally, with exception of [VO(mpp)(2)] and [VO(dmpp)(2)], all compounds exhibited scavenging activity against HOCl (39-81%) and the most efficient compounds were Cu(II) and Zn(II) complexes. Thus, these preliminary results uncover promising new metal ion complexes, inhibitors of neutrophil's oxidative burst, with potential anti-inflammatory properties, which may be seen as an useful strategy for further studies in the treatment of a number of diseases where oxidative damage is a serious issue. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2015.11.009

文献信息

• Distinctive EPR signals provide an understanding of the affinity of bis-(3-hydroxy-4-pyridinonato) copper(<scp>ii</scp>) complexes for hydrophobic environments
  作者：Maria Rangel、Andreia Leite、André M. N. Silva、Tânia Moniz、Ana Nunes、M. João Amorim、Carla Queirós、Luís Cunha-Silva、Paula Gameiro、John Burgess

  DOI：10.1039/c4dt00642a

  日期：——

  report the synthesis and characterization of a set of 3-hydroxy-4-pyridinone copper(II) complexes with variable lipophilicity. EPR spectroscopy was used to characterize the structure of copper(II) complexes in solution, and as a tool to gain insight into solvent interactions. EPR spectra of solutions of the [CuL2] complexes recorded in different solvents reveal the presence of two copper species whose ratio

  在这项工作中，我们报告了一组具有可变亲脂性的3-羟基-4-吡啶酮铜（II）配合物的合成和表征。EPR光谱用于表征溶液中铜（II）配合物的结构，并作为了解溶剂相互作用的工具。在不同溶剂中记录的[CuL 2 ]配合物溶液的EPR光谱显示存在两种铜，其比例取决于溶剂的性质。研究纯溶剂甲醇，二甲基亚砜，二氯甲烷及其与甲苯的50％（v / v）混合物中的EPR光谱可以表征两种类型的铜信号（g zz = 2.30和g zz= 2.26），其自旋哈密顿参数与溶剂化和非溶剂化的方平面铜（II）配合物一致。关于配体和配合物的潜在生物应用，以及对水-膜界面中分配特性的深入了解，在水饱和的辛醇，pH = 7.4的水溶液和脂质体悬浮液中也获得了代表三种化合物的EPR光谱。不同的亲脂性平衡。对脂质体中获得的EPR光谱进行分析，可以确定复合物在水相和脂质相中的位置。鉴于这项工作的结果，我们提出了使用EPR光谱法评估铜
• Metal self-assembly mimosine peptides with enhanced antimicrobial activity: towards a new generation of multitasking chelating agents
  作者：Joanna Izabela Lachowicz、Gabriele Dalla Torre、Rosita Cappai、Enrico Randaccio、Valeria M. Nurchi、Remigiusz Bachor、Zbigniew Szewczuk、Lukasz Jaremko、Mariusz Jaremko、Maria Barbara Pisano、Sofia Cosentino、Germano Orrù、Antonella Ibba、Joni Mujika、Xabier Lopez

  DOI：10.1039/c9dt04545g

  日期：——

  high-valent metals. Moreover, we demonstrate that these peptides show an anti-microbial activity against Gram positive bacteria that is enhanced by the formation of a complex with iron(iii) ions. The mimosine peptides could be an alternative to antimicrobial peptides (AMPs), which are expensive and susceptible to proteolytic degradation. In summary, in the present work, we propose a new generation of

  含羞氨酸是一种具有多种特性的非蛋白质氨基酸，例如具有抗菌，消炎，抗癌和抗病毒的特性。由于其与去铁酮（DFP）的结构相似性，因此它是一种潜在的优异金属螯合剂。在目前的工作中，我们结合实验和理论（DFT）方法来研究含羞草肽的特性。合成了六种不同的肽，并通过紫外可见分光光度法表征了其复杂的化学计量和稳定性。然后，使用DFT方法评估肽的结合模式和自组装特征，考虑到不同的含羞草氨基酸数量和不同的含羞草残基之间间隔区的长度，并且实验数据与计算计算。对这些肽的结构性质的进一步阐明使我们能够提出对含羞草部分结构的改进，从而可以提高对高价金属的亲和力。此外，我们证明了这些肽对革兰氏阳性细菌显示出抗微生物活性，该活性通过与铁（iii）离子形成复合物而增强。含羞草肽可以替代抗菌肽（AMPs），后者价格昂贵并且易于蛋白水解降解。总而言之，在目前的工作中，我们提出了新一代的基于多功能含羞草素的肽作为新型金属自组装螯