2,2',2''-(10-(2-((6-(4-benzoyl-2-oxo-9,10-dihydro-2H-pyrano[2,3-f]quinolin-7(8H)-yl)hexyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid | 944413-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2',2''-(10-(2-((6-(4-benzoyl-2-oxo-9,10-dihydro-2H-pyrano[2,3-f]quinolin-7(8H)-yl)hexyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
• CAS: 944413-69-8
• 化学式: C₄₁H₅₄N₆O₁₀
• 分子量: 790.914
• InChiKey: HZWZHSWSWJGVOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  57.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  204.48
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,2',2''-(10-(2-((6-(4-benzoyl-2-oxo-9,10-dihydro-2H-pyrano[2,3-f]quinolin-7(8H)-yl)hexyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 2-[4,7-bis(carboxymethyl)-10-[2-[6-[4-[hydroxy(phenyl)methyl]-2-oxo-9,10-dihydro-8H-pyrano[2,3-f]quinolin-7-yl]hexylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
  参考文献：
  名称：

  Transposing Molecular Fluorescent Switches into the Near-IR:  Development of Luminogenic Reporter Substrates for Redox Metabolism

  摘要：

  This study reports the development of a Nd(III)-based near-IR luminescent probe for monitoring aldo-ketoreductase (AKR) enzyme activity. We have adapted a coumarin-based reporter substrate for the AKR1C2 to a near-IR emitting format by tethering the former to a macrocyclic Nd(III) moiety via an alkyl linker. Enzymatic reduction of the ketone functionality on the coumarin alters the energy transfer efficiency from the fluorophore to the emitting lanthanide species, resulting in emission at similar to 1060 nm from the alcohol product. The efficiency of sensitization is not significantly affected by extending the alkyl tether from two to three carbons, and even a six-carbon linker still supports viable sensitized luminescence. In addition, the suitability of these complexes to act as enzyme substrates improves with longer linker length. We have thus developed long wavelength luminogenic reporter substrates for a redox enzyme and also a general platform for transposing molecular fluorescence into the more desirable near-IR region.

  DOI：

  10.1021/ja071311d
• 作为产物：
  描述：

  methyl 4-oxo-4-phenylbut-2-ynoate 在 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 108.0h， 生成 2,2',2''-(10-(2-((6-(4-benzoyl-2-oxo-9,10-dihydro-2H-pyrano[2,3-f]quinolin-7(8H)-yl)hexyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
  参考文献：
  名称：

  Transposing Molecular Fluorescent Switches into the Near-IR:  Development of Luminogenic Reporter Substrates for Redox Metabolism

  摘要：

  This study reports the development of a Nd(III)-based near-IR luminescent probe for monitoring aldo-ketoreductase (AKR) enzyme activity. We have adapted a coumarin-based reporter substrate for the AKR1C2 to a near-IR emitting format by tethering the former to a macrocyclic Nd(III) moiety via an alkyl linker. Enzymatic reduction of the ketone functionality on the coumarin alters the energy transfer efficiency from the fluorophore to the emitting lanthanide species, resulting in emission at similar to 1060 nm from the alcohol product. The efficiency of sensitization is not significantly affected by extending the alkyl tether from two to three carbons, and even a six-carbon linker still supports viable sensitized luminescence. In addition, the suitability of these complexes to act as enzyme substrates improves with longer linker length. We have thus developed long wavelength luminogenic reporter substrates for a redox enzyme and also a general platform for transposing molecular fluorescence into the more desirable near-IR region.

  DOI：

  10.1021/ja071311d