(E)-2-(2-(8-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)-6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium trifluoroacetate | 1578116-07-0

• 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: (E)-2-(2-(8-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)-6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium trifluoroacetate
• CAS: 1578116-07-0
• 化学式: C₂F₃O₂*C₃₉H₅₄N₅O₂
• 分子量: 737.906
• InChiKey: IICBRJPOECGPSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  53.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  111.93
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(8-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)-6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium trifluoroacetate 、 溴甲苯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以28%的产率得到(E)-2-(2-(8-((8-benzyl-1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)-6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium trifluoroacetate
  参考文献：
  名称：

  A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO)

  摘要：

  The first near-infrared fluorescent turn-on sensor for the detection of nitroxyl (F(NO), the one-electron reduced form of nitric oxide (NO), is reported. The new copper-based probe, CuDHX1, contains a dihydroxanthene (DHX) fluorophore and a cyclam derivative as a Cu(II) binding site. Upon reaction with HNO, CuDHX1 displays a five-fold fluorescence turn-on in cuvettes and is selective for HNO over thiols and reactive nitrogen and oxygen species. CuDHX1 can detect exogenously applied HNO in live mammalian cells and in conjunction with the zinc-specific, green-fluorescent sensor ZP1 can perform multicolor/multianalyte microscopic imaging. These studies reveal that HNO treatment elicits an increase in the concentration of intracellular mobile zinc.

  DOI：

  10.1021/ja500315x
• 作为产物：
  描述：

  IR-780 碘化物 在 吡啶 、 氯化亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 (E)-2-(2-(8-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)-6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium trifluoroacetate
  参考文献：
  名称：

  A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO)

  摘要：

  The first near-infrared fluorescent turn-on sensor for the detection of nitroxyl (F(NO), the one-electron reduced form of nitric oxide (NO), is reported. The new copper-based probe, CuDHX1, contains a dihydroxanthene (DHX) fluorophore and a cyclam derivative as a Cu(II) binding site. Upon reaction with HNO, CuDHX1 displays a five-fold fluorescence turn-on in cuvettes and is selective for HNO over thiols and reactive nitrogen and oxygen species. CuDHX1 can detect exogenously applied HNO in live mammalian cells and in conjunction with the zinc-specific, green-fluorescent sensor ZP1 can perform multicolor/multianalyte microscopic imaging. These studies reveal that HNO treatment elicits an increase in the concentration of intracellular mobile zinc.

  DOI：

  10.1021/ja500315x