H(2,2)-1,2-HOPO | 221249-99-6

• 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: H(2,2)-1,2-HOPO
• 英文别名: N-[2-[2-[bis[2-[(1-hydroxy-6-oxo-pyridine-2-carbonyl)amino]ethyl]amino]ethyl-[2-[(1-hydroxy-6-oxo-pyridine-2-carbonyl)amino]ethyl]amino]ethyl]-1-hydroxy-6-oxo-pyridine-2-carboxamide；N-[2-[2-[bis[2-[(1-hydroxy-6-oxopyridine-2-carbonyl)amino]ethyl]amino]ethyl-[2-[(1-hydroxy-6-oxopyridine-2-carbonyl)amino]ethyl]amino]ethyl]-1-hydroxy-6-oxopyridine-2-carboxamide
• CAS: 221249-99-6
• 化学式: C₃₄H₄₀N₁₀O₁₂
• 分子量: 780.751
• InChiKey: VBXZHFRWDLEBNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  56
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  285
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  H(2,2)-1,2-HOPO 、 europium(III) chloride hexahydrate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  具有强水稳定性的八齿发光Eu（III）1,2-HOPO螯合物。

  摘要：

  两个新的配体5LINMe-1,2-HOPO（1）和H（2,2）-1,2-HOPO（2）的合成，表征和光物理性质，它们利用1,2-HOPO螯合物作为报告了一种用于Eu（III）的敏化剂。另外，通过X射线晶体学将先前的配体在结构上表征为Eu（III）络合物。四齿配体（1）的[Eu（1）2]-络合物在水溶液中稳定至约极限浓度。7x10（-9）M，并保留了1,2-HOPO敏化剂所具有的出色的光物理性能。相比之下，八齿配体（2）作为[Eu（2）]-络合物，经进一步稀释至极限浓度ca时，其稳定性大大提高。5x10（-17）M，超出大多数荧光计的最低可检测浓度。

  DOI：

  10.1021/ic700364t
• 作为产物：
  描述：

  H(2,2)-1,2-HOPOBn 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 72.0h， 生成 H(2,2)-1,2-HOPO
  参考文献：
  名称：

  Optimization of the Sensitization Process and Stability of Octadentate Eu(III) 1,2-HOPO Complexes

  摘要：

  The synthesis of a series of octadentate ligands containing the 1-hydroxypyridin-2-one (1,2-HOPO) group in complex with europium(III) is reported. Within this series, the central bridge connecting two diethylenetriamine units linked to two 1,2-HOPO chromophores at the extremities (5-LIN-1,2-HOPO) is varied from a short ethylene chain (H(2,2)-1,2-HOPO) to a long pentaethylene oxide chain (H(17O5,2)-1,2-HOPO). The thermodynamic stability of the europium complexes has been studied and reveals these complexes may be effective for biological measurements. Extension of the central bridge results in exclusion of the inner-sphere water molecule observed for [Eu(H(2,2)-1,2-HOPO)](-) going from a nonacoordinated to an octacoordinated Eu(III) ion. With the longer chain length ligands, the complexes display increased luminescence properties in aqueous medium with an optimum of 20% luminescence quantum yield for the [Eu(H(17O5,2)-1,2-HOPO)](-) complex. The luminescence properties for [Eu(H(14O4,2)-1,2-HOPO)](-) and [Eu(H(17O5,2)-1,2-HOPO)](-) are better than that of the model bis-tetradentate [Eu(5LIN(Me)-1,2-HOPO)(2)](-) complex, suggesting a different geometry around the metal center despite the geometric freedom allowed by the longer central chain in the H(mOn,2) scaffold. These differences are also evidenced by examining the luminescence spectra at room temperature and at 77 K and by calculating the luminescence kinetic parameters of the europium complexes.

  DOI：

  10.1021/acs.inorgchem.5b00748

文献信息

• [EN] RADIOPHARMACEUTICAL COMPLEXES<br/>[FR] COMPLEXES RADIOPHARMACEUTIQUES
  申请人：LUMIPHORE INC

  公开号：WO2011079291A1

  公开（公告）日：2011-06-30

  The invention provides compounds such as chelating agents useful in chelating metal ions, particularly radionuclides, to provide metal ion complexes. The invention also provides methods of using the compounds and complexes of the invention, such as in therapeutic and diagnostic applications.

  该发明提供了化合物，如螯合剂，可用于螯合金属离子，特别是放射性核素，以提供金属离子络合物。该发明还提供了使用该化合物和该发明的络合物的方法，例如在治疗和诊断应用中。
• LUMINESCENT 1-HYDROXY-2-PYRIDINONE CHELATES OF LANTHANIDES
  申请人：Raymond Kenneth N.

  公开号：US20100015725A1

  公开（公告）日：2010-01-21

  The present invention provides luminescent complexes between a lanthanide ion and an organic ligand which contains 1,2-hydroxypyridinone units. The complexes of the invention are stable in aqueous solutions and are useful as molecular probes, for example in medical diagnostics and bioanalytical assay systems. The invention also provides methods of using the complexes of the invention.

  本发明提供了一种含有1,2-羟基吡啶酮基团的有机配体和镧系离子之间的发光配合物。该发明的配合物在水溶液中稳定，并且可用作分子探针，例如在医学诊断和生物分析测量系统中。本发明还提供了使用所述配合物的方法。
• RADIOPHARMACEUTICAL COMPLEXES
  申请人：Xu Jide

  公开号：US20110189088A1

  公开（公告）日：2011-08-04

  The invention provides compounds such as chelating agents useful in chelating metal ions, particularly radionuclides, to provide metal ion complexes. The invention also provides methods of using the compounds and complexes of the invention, such as in therapeutic and diagnostic applications.

  该发明提供了一种化合物，例如螯合剂，可用于螯合金属离子，特别是放射性核素，以提供金属离子复合物。该发明还提供了使用该化合物和该发明的复合物的方法，例如在治疗和诊断应用中。
• MACROCYCLIC HOPO CHELATORS
  申请人：Butlin Nathaniel G.

  公开号：US20120214253A1

  公开（公告）日：2012-08-23

  The present invention provides a novel class of macrocyclic compounds as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds comprise hydroxypyridinonyl moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability.

  本发明提供了一类新型的大环化合物，以及由金属（例如镧系金属）离子和本发明中的化合物形成的络合物。优选的络合物在无需次级活化剂的情况下，具有高稳定性和高量子产率的镧系离子荧光。优选的化合物在它们的大环结构中包括羟基吡啶酮基团，并且其特点是与各种多肽（如抗体和蛋白质）具有惊人的低非特异性结合和高动力学稳定性。
• Macrocyclic HOPO chelators
  申请人：LUMIPHORE, INC.

  公开号：US10352938B2

  公开（公告）日：2019-07-16

  The present invention provides a novel class of macrocyclic compounds as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds comprise hydroxypyridinonyl moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability.

  本发明提供了一类新型大环化合物以及金属（如镧系元素）离子与本发明化合物之间形成的配合物。优选的配合物在水介质中表现出高稳定性和高镧系离子发光量子产率，无需使用二级活化剂。优选化合物在其大环结构中包含羟基吡啶壬基，其特点是与抗体和蛋白质等多种多肽的非特异性结合率低得出奇，并且具有很高的动力学稳定性。