10-(4-(bis(2-((carboxymethyl)thio)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-3H-5l5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-3-ide | 1202380-87-7

• 英文名称: 10-(4-(bis(2-((carboxymethyl)thio)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-3H-5l5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-3-ide
• CAS: 1202380-87-7
• 化学式: C₂₇H₃₂BF₂N₃O₄S₂
• 分子量: 575.509
• InChiKey: VYUISOIKXCAZKR-UHFFFAOYSA-N

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

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 10-(4-(bis(2-((carboxymethyl)thio)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-3H-5l5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-3-ide 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到10-(4-(bis(2-((2-(acetoxymethoxy)-2-oxoethyl)thio)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-3H-5l5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-3-ide
  参考文献：
  名称：

  A Turn-On Fluorescent Sensor for Detecting Nickel in Living Cells

  摘要：

  We present the synthesis and properties of Nickelsensor-1 (NS1), a new water-soluble, turn-on fluorescent sensor that is capable of selectively responding to Ni2+ in aqueous solution and in living cells. NS1 combines a BODIPY chromophore and a mixed N/O/S receptor to provide good selectivity for Ni2+ over a range of biologically abundant metal ions in aqueous solution. In addition to these characteristics, confocal microscopy experiments further show that NS1 can be delivered into living cells and report changes in intracellular Ni2+ levels in a respiratory cell model.

  DOI：

  10.1021/ja906500m
• 作为产物：
  描述：

  10-(4-(bis(2-((2-methoxy-2-oxoethyl)thio)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-3H-5l5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-3-ide 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以71%的产率得到10-(4-(bis(2-((carboxymethyl)thio)ethyl)amino)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-3H-5l5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-3-ide
  参考文献：
  名称：

  A Turn-On Fluorescent Sensor for Detecting Nickel in Living Cells

  摘要：

  We present the synthesis and properties of Nickelsensor-1 (NS1), a new water-soluble, turn-on fluorescent sensor that is capable of selectively responding to Ni2+ in aqueous solution and in living cells. NS1 combines a BODIPY chromophore and a mixed N/O/S receptor to provide good selectivity for Ni2+ over a range of biologically abundant metal ions in aqueous solution. In addition to these characteristics, confocal microscopy experiments further show that NS1 can be delivered into living cells and report changes in intracellular Ni2+ levels in a respiratory cell model.

  DOI：

  10.1021/ja906500m

文献信息

• Probing the Ni ²⁺ ‐selective Response of Fluorescent Probe NiSensor‐1 with the NiCast Photocaged Complex ^† ^‡
  作者：Erin E. Hickey、Daniel P. Kennedy、Celina Gwizdala、Prem N. Basa、Peter Müller、John MacDonald、Shawn C. Burdette

  DOI：10.1111/php.13567

  日期：2022.3

  reported to be selective for Ni2+. Other metal ions such as Zn2+ do not produce an emission response in aqueous solution. To investigate the coordination chemistry and selectivity of this receptor, we prepared NiCast, a photocage containing the CTEA receptor. Cast photocages undergo a photoreaction that decreases electron density on a metal-bound aniline nitrogen atom, which shifts the binding equilibrium

  CTEA ( N,N -bis[2-(carboxylmethyl)thioethyl]amine) 是一种混合供体配体，已被整合到多种荧光传感器中，例如 NiSensor-1，据报道该传感器对 Ni 2+具有选择性。其他金属离子如 Zn 2+在水溶液中不产生发射响应。为了研究这种受体的配位化学和选择性，我们制备了 NiCast，一种含有 CTEA 受体的光笼。铸造光笼发生光反应，降低了金属结合的苯胺氮原子上的电子密度，从而使结合平衡向未结合的金属离子移动。通过测量 NiCast 和 CTEA 受体对 Ni 2+、Zn 2+的结合亲和力来检验 CTEA 的独特选择性, Cd 2+和Cu 2+在不同条件下。在水溶液中，Ni 2+与苯胺氮原子的结合比Cd 2+强；然而，在 CH 3 CN 中，亲和力的变化实际上消失了。还分析了 [Cu(CTEA)] 的晶体结构，它表现出 Jahn-Teller