4-[2-[5-[1-[6-(2,5-Dioxopyrrolidin-1-yl)oxy-6-oxohexyl]-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]butane-1-sulfonate | 881178-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[2-[5-[1-[6-(2,5-Dioxopyrrolidin-1-yl)oxy-6-oxohexyl]-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]butane-1-sulfonate
• 英文别名: 4-[2-[5-[1-[6-(2,5-dioxopyrrolidin-1-yl)oxy-6-oxohexyl]-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]butane-1-sulfonate
• CAS: 881178-43-4；942205-51-8
• 化学式: C₃₉H₄₇N₃O₁₃S₃
• 分子量: 862.012
• InChiKey: HZPNKOUHLQOKCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  58
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  261
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-[2-[5-[1-[6-(2,5-Dioxopyrrolidin-1-yl)oxy-6-oxohexyl]-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]butane-1-sulfonate 以 水 为溶剂， 反应 1.0h， 生成 C₄₃H₅₁N₇O₁₆S₃
  参考文献：
  名称：

  Detection of TNT in Water Using an Evanescent Wave Fiber-Optic Biosensor

  摘要：

  A general health hazard from explosive toxicity exists due to poor storage facilities for explosives and from contamination of soil and water with byproducts of explosive manufacture. To provide an effective method for monitoring water contamination, the Naval Research Laboratory's fiber-optic biosensor was adapted for the detection of small molecules such as explosives. A competitive immunoassay was developed for the detection of the most widely used explosive, trinitrotoluene (TNT). Trinitrobenzenesulfonic acid (TNB), an analog of TNT, was labeled with a fluorophore and used as the analyte competitor. A solution containing 7.5 ng/mL sulfoindocyanine 5-ethylenediamine-labeled TNB (Cy5-EDA-TNB) was exposed to an antibody-coated optical fiber, generating a specific signal above background that corresponds to the 100% or reference signal. Inhibition of the 100% signal was proportional to the TNT concentration in the sample. Detection sensitivities of 10 ng/mL TNT (8 ppb) in buffer were achieved. Tests on river, harbor, and bilge water samples spiked with TNT showed results similar to tests on laboratory (buffer matrix) samples. To determine possible interferences, several structural analogs of TNT were tested.

  DOI：

  10.1021/ac00110a018
• 作为产物：
  描述：

  1-(5-羧基己基)-2,3,3-三甲基-3H-吲哚-5-磺酸内盐 在 乙酸酐 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 4-[2-[5-[1-[6-(2,5-Dioxopyrrolidin-1-yl)oxy-6-oxohexyl]-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]butane-1-sulfonate
  参考文献：
  名称：

  基于2,3-二甲基-3-（4-磺丁基）-3 H-吲哚-5-磺酸的水溶性茚二羰花青染料

  摘要：

  合成了一系列基于2,3-二甲基-3-（4-磺丁基）-3 H-吲哚-5-磺酸的单反应性水溶性茚二羰花青染料。这些染料除了在偶氮烯端基中还包含（最多3个）磺基烷基外，还包含两个芳族磺基。研究了磺丁基的数量和位置对溶液中游离染料以及与抗体（IgG）结合后染料的光谱性质和光稳定性的影响。这些染料的最大吸收在649和653 nm之间，摩尔吸收率在240,000和256,000 M -1  cm -1之间，最大发射波长在668至672 nm之间，游离形式的荧光量子产率在28％至32％之间，与IgG结合时可达到43％。这些染料与磺基基团的数量无关，在水中浓度高达5×10 -5  M时没有聚集。发现磺基烷基基团的数量与IgG共轭染料的荧光量子产率和光稳定性直接相关。

  DOI：

  10.1016/j.dyepig.2012.09.007

文献信息

• Water soluble indodicarbocyanine dyes based on 2,3-dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid
  作者：Larysa I. Markova、Iryna A. Fedyunyayeva、Yevgen A. Povrozin、Olga M. Semenova、Sania U. Khabuseva、Ewald A. Terpetschnig、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2012.09.007

  日期：2013.2

  mono-reactive, water-soluble, indodicarbocyanine dyes based on 2,3-dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid was synthesized. These dyes contain two aromatic sulfo groups and in addition to (up to 3) sulfoalkyl groups in the indolenine end groups. The impact of the number and position of sulfobutyl groups on the spectral properties and photostabilities of the dyes free in solutions and after binding to

  合成了一系列基于2,3-二甲基-3-（4-磺丁基）-3 H-吲哚-5-磺酸的单反应性水溶性茚二羰花青染料。这些染料除了在偶氮烯端基中还包含（最多3个）磺基烷基外，还包含两个芳族磺基。研究了磺丁基的数量和位置对溶液中游离染料以及与抗体（IgG）结合后染料的光谱性质和光稳定性的影响。这些染料的最大吸收在649和653 nm之间，摩尔吸收率在240,000和256,000 M -1  cm -1之间，最大发射波长在668至672 nm之间，游离形式的荧光量子产率在28％至32％之间，与IgG结合时可达到43％。这些染料与磺基基团的数量无关，在水中浓度高达5×10 -5  M时没有聚集。发现磺基烷基基团的数量与IgG共轭染料的荧光量子产率和光稳定性直接相关。
• Detection of TNT in Water Using an Evanescent Wave Fiber-Optic Biosensor
  作者：Lisa C. Shriver-Lake、Kristen A. Breslin、Paul T. Charles、David W. Conrad、Joel P. Golden、Frances S. Ligler

  DOI：10.1021/ac00110a018

  日期：1995.7.15

  A general health hazard from explosive toxicity exists due to poor storage facilities for explosives and from contamination of soil and water with byproducts of explosive manufacture. To provide an effective method for monitoring water contamination, the Naval Research Laboratory's fiber-optic biosensor was adapted for the detection of small molecules such as explosives. A competitive immunoassay was developed for the detection of the most widely used explosive, trinitrotoluene (TNT). Trinitrobenzenesulfonic acid (TNB), an analog of TNT, was labeled with a fluorophore and used as the analyte competitor. A solution containing 7.5 ng/mL sulfoindocyanine 5-ethylenediamine-labeled TNB (Cy5-EDA-TNB) was exposed to an antibody-coated optical fiber, generating a specific signal above background that corresponds to the 100% or reference signal. Inhibition of the 100% signal was proportional to the TNT concentration in the sample. Detection sensitivities of 10 ng/mL TNT (8 ppb) in buffer were achieved. Tests on river, harbor, and bilge water samples spiked with TNT showed results similar to tests on laboratory (buffer matrix) samples. To determine possible interferences, several structural analogs of TNT were tested.