| 1397866-98-6

• CAS: 1397866-98-6
• 化学式: C₂₂H₂₆BF₂N₃
• 分子量: 381.276
• InChiKey: AFZALMCBEBWSEQ-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：

  以 丙酮 为溶剂， 反应 18.0h， 生成 COP-1
  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
• 作为产物：
  描述：

  在 sodium sulfide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  基于活性的传感的配体导向方法：开发能够检测内源性一氧化碳的钯环荧光探针

  摘要：

  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

  DOI：

  10.1021/jacs.0c06405

文献信息

• 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。
• Near-infrared fluorogenic imaging of carbon monoxide in live cells using palladium-mediated carbonylation
  作者：Zhi-Yi Xiao、Bing-Lun Tu、Shan-Hong Hua、Fenglin Wang、Li-Juan Tang、Wan-Rong Dong、Jian-Hui Jiang

  DOI：10.1039/d3cc04523d

  日期：——

  Here we develop a near infrared (NIR) fluorogenic probe for carbon monoxide (CO) detection and imaging based on palladium-mediated carbonylation using a NIR boron-dipyrromethene difluoride as a fluorophore and tetraethylene glycols as aqueous moieties. The probe is utilized to image exogenous and endogenous CO under different stimulated conditions in live cells.

  在这里，我们开发了一种近红外（NIR）荧光探针，用于基于钯介导的羰基化的一氧化碳（CO）检测和成像，使用近红外硼二吡咯亚甲基二氟化物作为荧光团和四甘醇作为水基部分。该探针用于对活细胞中不同刺激条件下的外源性和内源性 CO 进行成像。
• Development of a water-soluble 3-formylBODIPY dye for fluorogenic sensing and cell imaging of sulfur dioxide derivatives
  作者：Murat Işık、Ilke Simsek Turan、Suay Dartar

  DOI：10.1016/j.tetlet.2019.04.039

  日期：2019.5

  A new water-soluble, highly fluorogenic 3-formylBODIPY dye that enables the sensing of SO2 derivatives in aqueous buffers and cancer cells is reported. The quaternary ammonium group appended through the mesa-position of the BODIPY dye ensures water solubility. The probe exhibits high specificity for cytosolic (bi)sulfites and fluoresces brightly in human lung adenocarcinoma cells (A549). (C) 2019 Elsevier Ltd. All rights reserved.