5-(2,2-Difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-2-[(dimethylamino)methyl]benzoic acid | 1397867-01-4

• 分子结构分类: 有机化合物
• 英文名称: 5-(2,2-Difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-2-[(dimethylamino)methyl]benzoic acid
• 英文别名: 5-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-2-[(dimethylamino)methyl]benzoic acid
• CAS: 1397867-01-4
• 化学式: C₂₃H₂₆BF₂N₃O₂
• 分子量: 425.286
• InChiKey: FNYWNOASVVMRBP-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

• 作为产物：
  描述：

  以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 32.0h， 生成 5-(2,2-Difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-2-[(dimethylamino)methyl]benzoic acid
  参考文献：
  名称：

  A Reaction-Based Fluorescent Probe for Selective Imaging of Carbon Monoxide in Living Cells Using a Palladium-Mediated Carbonylation

  摘要：

  Carbon monoxide is a member of the gasotransmitter family, which also includes NO and H2S, and has been implicated in a variety of pathological and physiological conditions. Whereas exogenous therapeutic additions of CO to tissues and whole animals have been well-studied, the real-time spatial and temporal tracking of CO at the cellular level remains an open challenge. Here we report a new type of turn-on fluorescent probe for selective CO detection based on palladium-mediated carbonylation reactivity. CO Probe 1 (COP-1) is capable of detecting CO both in aqueous buffer and in live cells with high selectivity over a range of biologically relevant reactive small molecules, providing a potentially powerful approach for interrogating its chemistry in biological systems.

  DOI：

  10.1021/ja307017b

文献信息

• Ligand-Directed Approach to Activity-Based Sensing: Developing Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide Detection
  作者：Johannes Morstein、Denis Höfler、Kohei Ueno、Jonah W. Jurss、Ryan R. Walvoord、Kevin J. Bruemmer、Samir P. Rezgui、Thomas F. Brewer、Minoru Saitoe、Brian W. Michel、Christopher J. Chang

  DOI：10.1021/jacs.0c06405

  日期：2020.9.16

  with CO under physiological conditions. These fundamental studies led to the development of an optimized probe, termed Carbon Monoxide Probe-3 Ester Pyridine (COP-3E-Py), which enables imaging of CO release in live cell and brain settings, including monitoring of endogenous CO production that triggers presynaptic dopamine release in fly brains. This work provides a unique tool for studying CO in living

  一氧化碳 (CO) 是一种新兴的气体递质和活性碳物质，具有广泛的抗炎、细胞保护和神经递质功能以及治疗心血管疾病的潜力。与 NO 和 H2S 等其他主要气体传递体相比，生物学和医学中的 CO 化学研究仍然具有挑战性，这在很大程度上是由于可用于直接可视化复杂生命系统中这种瞬态和自由扩散的小分子的可用工具的局限性。在这里，我们报告了一种通过钯介导的羰基化化学检测一氧化碳的配体导向的基于活性的传感 (ABS) 方法。具体而言，设计和合成一系列在钯配体环境中具有系统改变的 ABS 探针（例如 sp3-S、sp3-N、sp2-N) 建立钯环的构效关系，以赋予生理条件下与 CO 的选择性反应性。这些基础研究导致开发了一种优化的探针，称为一氧化碳探针-3 酯吡啶 (COP-3E-Py)，它能够对活细胞和大脑环境中的 CO 释放进行成像，包括监测触发突触前的内源性 CO 产生果蝇大脑中的多巴胺释放。这项工作为研究生命系统中的
• Reaction-based fluorescent probe for selective detection of carbon monoxide using metal-mediated carbonylation
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US09329191B2

  公开（公告）日：2016-05-03

  Carbon monoxide (CO) is a member of the gasotransmitter family that includes NO and H2S and is implicated in a variety of pathological and physiological conditions. Whereas exogenous therapeutic additions of CO to tissues and whole animals have been well studied, the real-time spatial and temporal tracking of CO at the cellular level remains an open challenge. We now report a new type of turn-on fluorescent probe for selective CO detection by exploiting palladium-mediated carbonylation reactivity. The compounds of the invention are capable of detecting CO both in aqueous buffer and in live cells with high selectivity over a range of biologically relevant reactive small molecules, providing a potentially powerful approach for interrogating its chemistry in biological systems.

  一氧化碳（CO）是气体传递物家族的成员之一，包括NO和H2S，并且与各种病理和生理条件有关。虽然对组织和整个动物体内外源性治疗添加CO的研究已经很充分，但在细胞水平实时空间和时间跟踪CO仍然是一个开放性挑战。我们现在报告了一种新型的打开式荧光探针，通过利用钯介导的羰基化反应来选择性检测CO。该发明的化合物能够在水性缓冲液和活细胞中高选择性地检测CO，同时在一系列生物相关的反应性小分子中提供了一种潜在强大的方法，用于研究其在生物系统中的化学性质。