2-[2-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyldisulfanyl]ethyl]-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one | 1140911-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-[2-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyldisulfanyl]ethyl]-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
• CAS: 1140911-17-6
• 化学式: C₆₀H₆₈N₆O₄S₂
• 分子量: 1001.37
• InChiKey: FMHDPEMTVWPYQY-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  72
• 可旋转键数：
  19
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-[2-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyldisulfanyl]ethyl]-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one 在 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以19%的产率得到2-[2-[2-[3',6'-Bis(diethylamino)-3-sulfanylidenespiro[isoindole-1,9'-xanthene]-2-yl]ethyldisulfanyl]ethyl]-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-thione
  参考文献：
  名称：

  Dithiolane linked thiorhodamine dimer for Hg2+ recognition in living cells

  摘要：

  基于硫代罗丹明的化学传感器A，作为一种二硫键连接的二聚体，因其对硫的高亲和力而被设计用于Hg²⁺的识别。光谱学结果显示，与其他阳离子相比，化学传感器A对Hg²⁺具有实时响应、高灵敏度和选择性。这些性质在机制上归因于通过Hg²⁺诱导的去硫化作用，从罗丹明螺内酯转化为噻唑啉衍生的开环罗丹明。通过预处理了A的活细胞中Hg²⁺的体外识别实验表明，可成像的Hg²⁺浓度达到了人类的安全界限。

  DOI：

  10.1039/b815956d
• 作为产物：
  描述：

  cystamine dihydrochioride 、 罗丹明B 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以57.1%的产率得到2-[2-[2-[3',6'-Bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]ethyldisulfanyl]ethyl]-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
  参考文献：
  名称：

  A new rhodamine-based fluorescent chemosensor for Fe3+ and its application in living cell imaging

  摘要：

  A new rhodamine-based compound (1) has been synthesized and applied as an "off-on" chemosensor for Fe3+. The comparison of this method with some other fluorescence methods for Fe3+ indicates that the method can detect Fe3+ in living cells by fluorescence enhancement and color changes with high sensitivity and selectivity. The fluorescence intensity of 1 is significantly increased about 60-fold with 20 equiv of Fe3+ added. Most importantly, the fluorescence changes of the chemosensor are remarkably specific for Fe3+ in the presence of other metal ions, which meet the selective requirements for practical application. Moreover, the experiment results show that the response behavior of 1 towards Fe3+ is pH independent in neutral condition (pH 6.0-8.0) and the response of the chemosensor is fast (response time less than 2 min). In addition, the proposed chemosensor has been used for imaging of Fe3+ in living cells with satisfying results. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.01.003

文献信息

• Dithiolane linked thiorhodamine dimer for Hg2+ recognition in living cells
  作者：Weimin Liu、Liwei Xu、Hongyan Zhang、Juanjuan You、Xiaoling Zhang、Ruilong Sheng、Huaping Li、Shikang Wu、Pengfei Wang

  DOI：10.1039/b815956d

  日期：——

  Thiorhodamine-based chemodosimeter A, a disulfide linked dimer, was designed for Hg2+ recognition by virtue of the strong affinity of mercury for sulfur. Spectroscopic results reveal that chemodosimeter A exhibits real-time responses, and high sensitivity and selectivity for Hg2+ in comparison to other cations. These properties are mechanistically ascribed to the transfer from rhodamine spirolactam to the thiazoline-derived open-ring rhodamineviaHg2+ induced desulfurization. The in vitro recognition of Hg2+ in living cells pretreated with A was examined, showing that the concentration of Hg2+ that could be imaged reaches the safety limit for human beings.

  基于硫代罗丹明的化学传感器A，作为一种二硫键连接的二聚体，因其对硫的高亲和力而被设计用于Hg²⁺的识别。光谱学结果显示，与其他阳离子相比，化学传感器A对Hg²⁺具有实时响应、高灵敏度和选择性。这些性质在机制上归因于通过Hg²⁺诱导的去硫化作用，从罗丹明螺内酯转化为噻唑啉衍生的开环罗丹明。通过预处理了A的活细胞中Hg²⁺的体外识别实验表明，可成像的Hg²⁺浓度达到了人类的安全界限。
• A new rhodamine-based fluorescent chemosensor for Fe3+ and its application in living cell imaging
  作者：Chun-Yan Li、Chun-Xiang Zou、Yong-Fei Li、Jia-Liang Tang、Chao Weng

  DOI：10.1016/j.dyepig.2014.01.003

  日期：2014.5

  A new rhodamine-based compound (1) has been synthesized and applied as an "off-on" chemosensor for Fe3+. The comparison of this method with some other fluorescence methods for Fe3+ indicates that the method can detect Fe3+ in living cells by fluorescence enhancement and color changes with high sensitivity and selectivity. The fluorescence intensity of 1 is significantly increased about 60-fold with 20 equiv of Fe3+ added. Most importantly, the fluorescence changes of the chemosensor are remarkably specific for Fe3+ in the presence of other metal ions, which meet the selective requirements for practical application. Moreover, the experiment results show that the response behavior of 1 towards Fe3+ is pH independent in neutral condition (pH 6.0-8.0) and the response of the chemosensor is fast (response time less than 2 min). In addition, the proposed chemosensor has been used for imaging of Fe3+ in living cells with satisfying results. (C) 2014 Elsevier Ltd. All rights reserved.