2-[4,10-bis(2-amino-2-oxoethyl)-7-[2-[(4-methyl-2-oxo-1H-quinolin-7-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide | 944149-98-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[4,10-bis(2-amino-2-oxoethyl)-7-[2-[(4-methyl-2-oxo-1H-quinolin-7-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide
• CAS: 944149-98-8
• 化学式: C₂₆H₃₉N₉O₅
• 分子量: 557.653
• InChiKey: KNULPZLSVAPTLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  200
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[4,10-bis(2-amino-2-oxoethyl)-7-[2-[(4-methyl-2-oxo-1H-quinolin-7-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide 、 europium(III) chloride hexahydrate 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Cocktails of Tb³⁺ and Eu³⁺ Complexes:  A General Platform for the Design of Ratiometric Optical Probes

  摘要：

  Fluorescent and luminescent reporters that signal molecular events of interest by modulating the ratio of peaks in their emission profile have advantages over reporters that simply modulate their emission intensity, since ratiometric measurement is concentration-independent and allows them to be effective in complex contexts, such as living cells or sensor microarrays. We herein describe a general platform for the design of ratiometric probes based on a heterometallic Tb3+/Eu3+ bis-lanthanide ensemble, consisting of a mixture, or "cocktail", of otherwise identical heterometalated chelates. The chelate contains an organic photon antenna that sensitizes the Tb3+/Eu3+ luminescence. The contributions of the two metals to the composite luminescence spectrum can be tuned to the same relative scale by adjusting the stoichiometry of the cocktail, allowing subtle changes in their ratio to be accurately measured. Importantly, the ratio responds to chemical and environmental changes experienced by the photon antenna, making the system an ideal platform for the design of chemical and enzymatic probes. As proofs of concept, we describe a ratiometric probe for esterase activity and a polarity-responsive ratiometric sensor.

  DOI：

  10.1021/ja070867y
• 作为产物：
  描述：

  2-氯-N-(4-甲基-2-氧代-1,2-二氢-7-喹啉基)乙酰胺 在 N,N-二异丙基乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-[4,10-bis(2-amino-2-oxoethyl)-7-[2-[(4-methyl-2-oxo-1H-quinolin-7-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide
  参考文献：
  名称：

  Cocktails of Tb³⁺ and Eu³⁺ Complexes:  A General Platform for the Design of Ratiometric Optical Probes

  摘要：

  Fluorescent and luminescent reporters that signal molecular events of interest by modulating the ratio of peaks in their emission profile have advantages over reporters that simply modulate their emission intensity, since ratiometric measurement is concentration-independent and allows them to be effective in complex contexts, such as living cells or sensor microarrays. We herein describe a general platform for the design of ratiometric probes based on a heterometallic Tb3+/Eu3+ bis-lanthanide ensemble, consisting of a mixture, or "cocktail", of otherwise identical heterometalated chelates. The chelate contains an organic photon antenna that sensitizes the Tb3+/Eu3+ luminescence. The contributions of the two metals to the composite luminescence spectrum can be tuned to the same relative scale by adjusting the stoichiometry of the cocktail, allowing subtle changes in their ratio to be accurately measured. Importantly, the ratio responds to chemical and environmental changes experienced by the photon antenna, making the system an ideal platform for the design of chemical and enzymatic probes. As proofs of concept, we describe a ratiometric probe for esterase activity and a polarity-responsive ratiometric sensor.

  DOI：

  10.1021/ja070867y

文献信息

• Coordination Environment-Controlled Photoinduced Electron Transfer Quenching in Luminescent Europium Complexes
  作者：Daniel Kovacs、Emilie Mathieu、Salauat R. Kiraev、Jordann A. L. Wells、Ellen Demeyere、Agnès Sipos、K. Eszter Borbas

  DOI：10.1021/jacs.0c05518

  日期：2020.7.29

  ns and ms timescales. The contribution of photoinduced electron transfer to the overall reduction of the Eu(III) luminescence quantum yield was found to be comparable, and in many cases, larger than the quenching caused by well-established processes such as coupling to X-H oscillators. These results suggest that the elimination or mitigation of photoinduced electron transfer could substantially improve

  研究了通过光诱导电子从激发的光捕获天线到 Eu(III) 的转移对敏化 Eu(III) 发光的猝灭。制备了一系列包含不同金属结合位点并因此具有不同 Eu(III)/Eu(II) 还原电位的配合物。使用单晶 X 射线晶体学和顺磁 1 H NMR 光谱的组合对配合物进行了充分表征，其结果支持配合物的结构相似性。使用循环伏安法以及 ns 和 ms 时间尺度上的稳态和时间分辨发射光谱研究了 Eu(III) 中心和光捕获天线的氧化还原和光物理行为。发现光致电子转移对 Eu(III) 发光量子产率的整体降低的贡献是可比的，并且在许多情况下，大于由成熟过程（例如与 XH 振荡器耦合）引起的猝灭。这些结果表明，消除或减轻光致电子转移可以显着改善广泛使用的 Eu(III) 基发射器的发射特性。