4-[2-[5-[5-(Carboxymethyl)-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[2-[5-[5-(Carboxymethyl)-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate
• 化学式: C₃₇H₄₂N₂O₅S
• 分子量: 626.817
• InChiKey: JAHVGIHFUBWUEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 4-[2-[5-[5-(Carboxymethyl)-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 生成 NIR664 succinimidyl ester
  参考文献：
  名称：

  Visible Diode Laser-Induced Fluorescence Detection in Liquid Chromatography after Precolumn Derivatization of Amines

  摘要：

  To fully exploit the attractive visible diode laser-induced fluorescence (LIF) detection technique in column liquid chromatography (LC), covalent labeling procedures need to be developed which are compatible with near-infrared fluorescence. For this purpose, several red-absorbing labels containing a single succinimidyl ester functionality were synthesized and used for the derivatization of primary and secondary amines. Oxazines/thiazines, squaraines, and dicarbocyanines were examined as red-absorbing fluorophores. The quality of the LC-diode LIF system for the analytes concerned is illustrated by the concentration detection limit of the labeled n-octylamine (a test compound), which was as low as 2 x 10(-12) M. As expected in view of the limited reactivity of the succinimidyl ester group, the analyte concentrations required to obtain quantitative reaction with the label were equal to or higher than 2 x 10(-8) M. To show the applicability of the method to biological samples, urine was spiked with 5 x 10(-7) M. 1-adamantanamine, extracted, derivatized with a dicarbocyanine-based label, and analyzed by LC-diode LIF.

  DOI：

  10.1021/ac00106a015
• 作为产物：
  描述：

  、 5-Carboxymethyl-1-ethyl-2,3,3-trimethyl-3H-indolium; iodide 在 盐酸 、 potassium acetate 作用下， 生成 4-[2-[5-[5-(Carboxymethyl)-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate 、
  参考文献：
  名称：

  Visible Diode Laser-Induced Fluorescence Detection in Liquid Chromatography after Precolumn Derivatization of Amines

  摘要：

  To fully exploit the attractive visible diode laser-induced fluorescence (LIF) detection technique in column liquid chromatography (LC), covalent labeling procedures need to be developed which are compatible with near-infrared fluorescence. For this purpose, several red-absorbing labels containing a single succinimidyl ester functionality were synthesized and used for the derivatization of primary and secondary amines. Oxazines/thiazines, squaraines, and dicarbocyanines were examined as red-absorbing fluorophores. The quality of the LC-diode LIF system for the analytes concerned is illustrated by the concentration detection limit of the labeled n-octylamine (a test compound), which was as low as 2 x 10(-12) M. As expected in view of the limited reactivity of the succinimidyl ester group, the analyte concentrations required to obtain quantitative reaction with the label were equal to or higher than 2 x 10(-8) M. To show the applicability of the method to biological samples, urine was spiked with 5 x 10(-7) M. 1-adamantanamine, extracted, derivatized with a dicarbocyanine-based label, and analyzed by LC-diode LIF.

  DOI：

  10.1021/ac00106a015

文献信息

• Visible Diode Laser-Induced Fluorescence Detection in Liquid Chromatography after Precolumn Derivatization of Amines
  作者：A. J. G. Mank、H. T. C. van der Laan、H. Lingeman、C. Gooijer、U. A. Th. Brinkman、N. H. Velthorst

  DOI：10.1021/ac00106a015

  日期：1995.5.15

  To fully exploit the attractive visible diode laser-induced fluorescence (LIF) detection technique in column liquid chromatography (LC), covalent labeling procedures need to be developed which are compatible with near-infrared fluorescence. For this purpose, several red-absorbing labels containing a single succinimidyl ester functionality were synthesized and used for the derivatization of primary and secondary amines. Oxazines/thiazines, squaraines, and dicarbocyanines were examined as red-absorbing fluorophores. The quality of the LC-diode LIF system for the analytes concerned is illustrated by the concentration detection limit of the labeled n-octylamine (a test compound), which was as low as 2 x 10(-12) M. As expected in view of the limited reactivity of the succinimidyl ester group, the analyte concentrations required to obtain quantitative reaction with the label were equal to or higher than 2 x 10(-8) M. To show the applicability of the method to biological samples, urine was spiked with 5 x 10(-7) M. 1-adamantanamine, extracted, derivatized with a dicarbocyanine-based label, and analyzed by LC-diode LIF.