3,4,3-LI(1,2-HOPO)Bn | 460986-08-7

• 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: 3,4,3-LI(1,2-HOPO)Bn
• 英文别名: N,N'-(butane-1,4-diyl)bis(1-(benzyloxy)-N-(3-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)propyl)-6-oxo-1,6-dihydropyridine-2-carboxamide)；6-oxo-N-[3-[(6-oxo-1-phenylmethoxypyridine-2-carbonyl)-[4-[(6-oxo-1-phenylmethoxypyridine-2-carbonyl)-[3-[(6-oxo-1-phenylmethoxypyridine-2-carbonyl)amino]propyl]amino]butyl]amino]propyl]-1-phenylmethoxypyridine-2-carboxamide
• CAS: 460986-08-7
• 化学式: C₆₂H₆₂N₈O₁₂
• 分子量: 1111.22
• InChiKey: VDZMRDRPGADIPH-UHFFFAOYSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  82
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  217
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,4,3-LI(1,2-HOPO)Bn 在 盐酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 96.0h， 以81%的产率得到3,4,3-LI-1,2-HOPO dihydrochloride
  参考文献：
  名称：

  Hydroxypyridonate and hydroxypyrimidinone chelating agents

  摘要：

  本发明提供了羟基吡啶酮和羟基嘧啶酮螯合剂。还提供了这些剂的Gd(III)配合物，这些配合物可用作磁共振成像的造影增强剂。该发明还提供了制备本发明化合物的方法，以及在磁共振成像应用中使用这些化合物的方法。

  公开号：

  US20050008570A1
• 作为产物：
  描述：

  1-羟基-6-氧代-1,6-二氢吡啶-2-羧酸 在 4-二甲氨基吡啶 、 草酰氯 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成 3,4,3-LI(1,2-HOPO)Bn
  参考文献：
  名称：

  Sc-HOPO：一种用于放射性钪放射性药物的潜在构建体

  摘要：

  钪的三种同位素 — 43Sc、44Sc 和 47Sc — 分别作为成像和治疗的潜在候选物，以及作为元素匹配对的可能治疗诊断学使用，引起了越来越多的关注。在这里，我们提出了八齿螯合剂 3,4,3-（LI-1,2-HOPO）（或 HOPO），一种有效的硬阳离子螯合剂，作为一种潜在的配体，可用于在温和条件下具有简单放射性标记的放射性钪构建体。HOPO 形成 1：1 Sc-HOPO 复合物，在实验和理论上都得到了充分表征。[47Sc]Sc-HOPO 在 7 d 的化学和生物攻击中表现出良好的稳定性。在健康小鼠中，[43,47Sc]Sc-HOPO 迅速清除了身体，没有脱金属的迹象。HOPO 是用于放射性钪放射性药物的有力候选药物。

  DOI：

  10.1021/acs.inorgchem.2c03931

文献信息

• Synthesis and Initial Evaluation for In Vivo Chelation of Pu(IV) of a Mixed Octadentate Spermine-Based Ligand Containing 4-Carbamoyl-3-hydroxy-1-methyl-2(1<i>H</i>)-pyridinone and 6-Carbamoyl-1-hydroxy-2(1<i>H</i>)-pyridinone
  作者：Jide Xu、Patricia W. Durbin、Birgitta Kullgren、Shirley N. Ebbe、Linda C. Uhlir、Kenneth N. Raymond

  DOI：10.1021/jm010564t

  日期：2002.8.1

  An improved synthesis for a series of 1-hydroxy-2(1H)-pyridinone-based octadentate ligands is reported. The mixed chelate, octadentate ligand, 3,4,3-LI(1,2-Me-3,2-HOPO), was designed, synthesized, and tested for in vivo chelation of Pu in a mouse model. This ligand incorporates both 1,2-HOPO and Me-3,2-HOPO metal chelating units; the latter has higher affinity toward actinide ions than does 1,2-HOPO

  报道了一系列基于1-羟基-2（1H）-吡啶酮的八齿配体的合成方法的改进。设计，合成了混合的螯合物，八齿配体3,4,3-LI（1,2-Me-​​3,2-HOPO），并在小鼠模型中测试了Pu的体内螯合。该配体结合了1,2-HOPO和Me-3,2-HOPO金属螯合单元。在生理pH下，后者对act系离子的亲和力高于1,2-HOPO。以30 micromol / kg的标准临床剂量向禁食或正常喂养的小鼠口服或口服3,4,3-LI（1,2-HOPO）和3,4,3-LI（1,2-Me- 3,2-HOPO）除去注入的CaNa（3）DTPA明显更多的Pu。这些HOPO配体的0.1毫克/千克的注射剂量与30毫摩尔/千克的CaNa（3）DTPA注射一样有效。每天十次注射30 micromol / kg的HOPO配体未在小鼠中诱发可检测的急性毒性。口服时，混合的HOPO配体比3,4,3-LI（1,2-HOPO）更
• New Insights into Structure and Luminescence of Eu^III and Sm^III Complexes of the 3,4,3-LI(1,2-HOPO) Ligand
  作者：Lena J. Daumann、David S. Tatum、Benjamin E. R. Snyder、Chengbao Ni、Ga-lai Law、Edward I. Solomon、Kenneth N. Raymond

  DOI：10.1021/ja5116524

  日期：2015.3.4

  We report the preparation and new insight into photophysical properties of luminescent hydroxypyridonate complexes [(ML)-L-III](-) (M = Eu or Sm) of the versatile 3,4,3-LI(1,2-HOPO) ligand (L). We report the crystal structure of this ligand with Eu-III as well as insights into the coordination behavior and geometry in solution by using magnetic circular dichroism. In addition TD-DFT calculations were used to examine the excited states of the two different chromophores present in the 3,4,3-LI(1,2-HOPO) ligand. We find that the EuIII and SmIII complexes of this ligand undergo a transformation after in situ preparation to yield complexes with higher quantum yield (QY) over time. It is proposed that the lower QY in the in situ complexes is not only due to water quenching but could also be due to a lower degree of f-orbital overlap (in a kinetic isomer) as indicated by magnetic circular dichroism measurements.
• Alternative Chelator for⁸⁹Zr Radiopharmaceuticals: Radiolabeling and Evaluation of 3,4,3-(LI-1,2-HOPO)
  作者：Melissa A. Deri、Shashikanth Ponnala、Brian M. Zeglis、Gabor Pohl、J. J. Dannenberg、Jason S. Lewis、Lynn C. Francesconi

  DOI：10.1021/jm500389b

  日期：2014.6.12

  Zirconium-89 is an effective radionuclide for antibody-based positron emission tomography (PET) imaging because its physical half-life (78.41 h) matches the biological half-life of IgG antibodies. Desferrioxamine (DFO) is currently the preferred chelator for Zr-89(4+); however, accumulation of Zr-89 in the bones of mice suggests that Zr-89(4+) is released from DFO in vivo. An improved chelator for Zr-89(4+) could eliminate the release of osteophilic Zr-89(4+) and lead to a safer PET tracer with reduced background radiation dose. Herein, we present an octadentate chelator 3,4,3-(LI-1,2-HOPO) (or HOPO) as a potentially superior alternative to DFO. The HOPO ligand formed a 1:1 Zr-HOPO complex that was evaluated experimentally and theoretically. The stability of Zr-89-HOPO matched or surpassed that of Zr-89-DFO in every experiment. In healthy mice, Zr-89-HOPO cleared the body rapidly with no signs of demetalation. Ultimately, HOPO has the potential to replace DFO as the chelator of choice for Zr-89-based PET imaging agents.
• WO2008/8797
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• WO2007/121453
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