rhodamine B selenolactone | 1206830-39-8

• 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: rhodamine B selenolactone
• 英文别名: 3',6'-Bis(diethylamino)spiro[2-benzoselenophene-3,9'-xanthene]-1-one；3',6'-bis(diethylamino)spiro[2-benzoselenophene-3,9'-xanthene]-1-one
• CAS: 1206830-39-8
• 化学式: C₂₈H₃₀N₂O₂Se
• 分子量: 505.518
• InChiKey: KGEJVUWSURJLBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rhodamine B selenolactone 在 silver nitrate 作用下， 以 1,4-二氧六环 为溶剂， 生成 rhodamine B
  参考文献：
  名称：

  Imaging Different Interactions of Mercury and Silver with Live Cells by a Designed Fluorescence Probe Rhodamine B Selenolactone

  摘要：

  Rhodamine B selenolactone has been designed, synthesized, and characterized as a new fluorescent probe for imaging both Hg2+ and Ag+ in live cells to better understand their distinct toxicities to organisms. The probe is designed based on the fact that selenium has a strong affinity for mercury and silver, and is constructed by Incorporating a Se atom into the spirocyclic structure of rhodamine. It exhibits a rapid and specific spectroscopic off-on response to Hg2+ and Ag` instead of other species, with detection limits of 23 nM Hg2+ and 52 nM Ag+. Moreover, the probe is membrane-permeable, and can react with Ag+ even in the presence of Cl- because of the higher affinity of Se than Cl- for Ag+, which makes it of potential use for imaging not only Hg2+ but also Ag+ in live cells. This applicability has been demonstrated by imaging Hg2+ and Ag+ in Hela cells. It is observed that the reaction of Ag+ with the probe insido the cells occurs much slower than that of Hg2+, which is ascribed to the high concentration of cellular chloride ions inhibiting the formation of sufficient free Ag+. The present finding is helpful to get an insight into the different interaction mechanism of Hg2+ and Ag+ with cells, and more applications of the probe may be expected for studying the behaviors of Hg2+ and Ag+ in various biosystems.

  DOI：

  10.1021/ic902192a
• 作为产物：
  描述：

  罗丹明B盐酸盐 在 三氯氧磷 、 selenium 、 lithium aluminium tetrahydride 作用下， 以 1,2-二氯乙烷 、 四氢呋喃 为溶剂， 以40%的产率得到rhodamine B selenolactone
  参考文献：
  名称：

  Imaging Different Interactions of Mercury and Silver with Live Cells by a Designed Fluorescence Probe Rhodamine B Selenolactone

  摘要：

  Rhodamine B selenolactone has been designed, synthesized, and characterized as a new fluorescent probe for imaging both Hg2+ and Ag+ in live cells to better understand their distinct toxicities to organisms. The probe is designed based on the fact that selenium has a strong affinity for mercury and silver, and is constructed by Incorporating a Se atom into the spirocyclic structure of rhodamine. It exhibits a rapid and specific spectroscopic off-on response to Hg2+ and Ag` instead of other species, with detection limits of 23 nM Hg2+ and 52 nM Ag+. Moreover, the probe is membrane-permeable, and can react with Ag+ even in the presence of Cl- because of the higher affinity of Se than Cl- for Ag+, which makes it of potential use for imaging not only Hg2+ but also Ag+ in live cells. This applicability has been demonstrated by imaging Hg2+ and Ag+ in Hela cells. It is observed that the reaction of Ag+ with the probe insido the cells occurs much slower than that of Hg2+, which is ascribed to the high concentration of cellular chloride ions inhibiting the formation of sufficient free Ag+. The present finding is helpful to get an insight into the different interaction mechanism of Hg2+ and Ag+ with cells, and more applications of the probe may be expected for studying the behaviors of Hg2+ and Ag+ in various biosystems.

  DOI：

  10.1021/ic902192a

文献信息

• An unprecedented strategy for selective and sensitive fluorescence detection of nitric oxide based on its reaction with a selenide
  作者：Chengdong Sun、Wen Shi、Yanchao Song、Wei Chen、Huimin Ma

  DOI：10.1039/c1cc12174j

  日期：——

  A new strategy that utilizes the interaction between NO and a selenide is reported for fluorescence detection of NO, in which rhodamine B selenolactone serves as a model selenide.

  报道了一种利用NO与硒化物之间相互作用的新策略，用于实现NO的荧光检测，其中罗丹明B硒代内酯作为硒化物的模型。
• A selenolactone-based fluorescent chemodosimeter to monitor mecury/methylmercury species in vitro and in vivo
  作者：Xiaoqiang Chen、Kyung-Hwa Baek、Youngmee Kim、Sung-Jin Kim、Injae Shin、Juyoung Yoon

  DOI：10.1016/j.tet.2010.04.042

  日期：2010.6

  A fluorescent probe based on selenolactone displays unique fluorescence enhancement and UV vis spectral change for mercury/methylmercury species, which were attributed to deselenation reaction. The value of this system was successfully demonstrated by its use in detecting inorganic mercury/methylmercury species in cells and zebrafish. (C) 2010 Elsevier Ltd. All rights reserved.
• Imaging Different Interactions of Mercury and Silver with Live Cells by a Designed Fluorescence Probe Rhodamine B Selenolactone
  作者：Wen Shi、Shuna Sun、Xiaohua Li、Huimin Ma

  DOI：10.1021/ic902192a

  日期：2010.2.1

  Rhodamine B selenolactone has been designed, synthesized, and characterized as a new fluorescent probe for imaging both Hg2+ and Ag+ in live cells to better understand their distinct toxicities to organisms. The probe is designed based on the fact that selenium has a strong affinity for mercury and silver, and is constructed by Incorporating a Se atom into the spirocyclic structure of rhodamine. It exhibits a rapid and specific spectroscopic off-on response to Hg2+ and Ag` instead of other species, with detection limits of 23 nM Hg2+ and 52 nM Ag+. Moreover, the probe is membrane-permeable, and can react with Ag+ even in the presence of Cl- because of the higher affinity of Se than Cl- for Ag+, which makes it of potential use for imaging not only Hg2+ but also Ag+ in live cells. This applicability has been demonstrated by imaging Hg2+ and Ag+ in Hela cells. It is observed that the reaction of Ag+ with the probe insido the cells occurs much slower than that of Hg2+, which is ascribed to the high concentration of cellular chloride ions inhibiting the formation of sufficient free Ag+. The present finding is helpful to get an insight into the different interaction mechanism of Hg2+ and Ag+ with cells, and more applications of the probe may be expected for studying the behaviors of Hg2+ and Ag+ in various biosystems.