4-(3,3-dimethyl-2-(6-(phenylamino)hexa-1,3,5-trien-1-yl)-3H-indol-1-ium-1-yl)butane-1-sulfonate | 273383-41-8

• 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-(3,3-dimethyl-2-(6-(phenylamino)hexa-1,3,5-trien-1-yl)-3H-indol-1-ium-1-yl)butane-1-sulfonate
• CAS: 273383-41-8
• 化学式: C₂₆H₃₀N₂O₃S
• 分子量: 450.602
• InChiKey: DWRATLCSCIZCKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.24
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(3,3-dimethyl-2-(6-(phenylamino)hexa-1,3,5-trien-1-yl)-3H-indol-1-ium-1-yl)butane-1-sulfonate 在 sodium iodide 作用下， 以 甲醇 、 乙酸酐 为溶剂， 反应 4.33h， 生成
  参考文献：
  名称：

  Visible diode laser induced fluorescence detection in liquid chromatography after precolumn derivatization of thiols

  摘要：

  New cyanine labels containing only a single active group for the chemical derivatization of thiols were synthesized in order to apply visible diode laser induced fluorescence (DIO-LIF) detection in conventional-size liquid chromatography (LC). 2-Mercaptobenzothiazole (MBT) was selected as test compound. The most appropriate label was CY5.4a-IA, a sulfonated dicarbocyanine with a iodoacetamide reactive group. The detection limit of labeled MBT in the LC-DIO-LIF system was 8 X 10(-12) M. The detection limit of MBT was 1 x 10(-9) M; lower concentrations are not labeled quantitatively. The injection repeatability was 1.0% (n = 6), the reaction repeatability was 3.0% (n = 6), and linearity was observed from 2.5 X 10(-9) to 1.0 x 10(-5) M. As an example, MBT-spiked river water and urine samples were derivatized with CY5.4a-IA and analyzed by LC-DIO-LIF. Hardly any interference was found. The method compares very favorably with existing techniques.

  DOI：

  10.1021/ac00065a006
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 以 乙酸酐 为溶剂， 反应 0.5h， 生成 4-(3,3-dimethyl-2-(6-(phenylamino)hexa-1,3,5-trien-1-yl)-3H-indol-1-ium-1-yl)butane-1-sulfonate
  参考文献：
  名称：

  Visible diode laser induced fluorescence detection in liquid chromatography after precolumn derivatization of thiols

  摘要：

  New cyanine labels containing only a single active group for the chemical derivatization of thiols were synthesized in order to apply visible diode laser induced fluorescence (DIO-LIF) detection in conventional-size liquid chromatography (LC). 2-Mercaptobenzothiazole (MBT) was selected as test compound. The most appropriate label was CY5.4a-IA, a sulfonated dicarbocyanine with a iodoacetamide reactive group. The detection limit of labeled MBT in the LC-DIO-LIF system was 8 X 10(-12) M. The detection limit of MBT was 1 x 10(-9) M; lower concentrations are not labeled quantitatively. The injection repeatability was 1.0% (n = 6), the reaction repeatability was 3.0% (n = 6), and linearity was observed from 2.5 X 10(-9) to 1.0 x 10(-5) M. As an example, MBT-spiked river water and urine samples were derivatized with CY5.4a-IA and analyzed by LC-DIO-LIF. Hardly any interference was found. The method compares very favorably with existing techniques.

  DOI：

  10.1021/ac00065a006

文献信息

• Highly parallel nano-synthesis of cleavable peptide-dye conjugates on cellulose membranes
  作者：Kai Licha、Sarah Bhargava、Christiane Rheinländer、Andreas Becker、Jens Schneider-Mergener、Rudolf Volkmer-Engert

  DOI：10.1016/s0040-4039(00)00019-8

  日期：2000.3

  mercapto-functionalized cellulose membranes with preformed Fmoc-amino acid 3-bromopropyl esters yielded membrane-bound amino acids connected via a stable thioether and a cleavable ester bond. This synthesis strategy allows the highly parallel preparation of peptides that can be solubilized from the solid support. We apply this approach to the synthesis of novel peptide–cyanine dye conjugates which are

  用预先形成的Fmoc-氨基酸3-溴丙基酯处理巯基官能化的纤维素膜，产生通过稳定的硫醚和可裂解的酯键连接的膜结合氨基酸。这种合成策略允许高度平行地制备可从固体支持物中溶解的肽。我们将这种方法应用于新型肽-花青染料偶联物的合成，这些偶联物可能可用作靶向肿瘤特异性受体的荧光造影剂。