1,2,3,3-Tetramethyl-5-sulfo-3H-indol-1-ium iodide | 644979-02-2

• 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: 1,2,3,3-Tetramethyl-5-sulfo-3H-indol-1-ium iodide
• 英文别名: 1,2,3,3-tetramethylindol-1-ium-5-sulfonic acid;iodide
• CAS: 644979-02-2
• 化学式: C₁₂H₁₆NO₃S*I
• 分子量: 381.234
• InChiKey: NWSWGUAHXDVBLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.04
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,3-Tetramethyl-5-sulfo-3H-indol-1-ium iodide 、 α-mercaptopropionic acid β-anilineacrolein 在 乙酸酐 作用下， 反应 0.67h， 以60%的产率得到
  参考文献：
  名称：

  Structure-inherent near-infrared fluorescent probe mediates apoptosis imaging and targeted drug delivery in vivo

  摘要：

  Imaging of tumor apoptosis can provide invaluable information in regards to drug treatment effectiveness, drug development and tumor therapeutic response. Thus, the development of apoptotic specific and sensitive targeted fluorescence probes is critically needed. In this work, we developed a novel and simple one-step synthetic method for producing monocarboxylate near-infrared cyanine dyes. The hydrophobic cationic dyes possess advantageous optical properties and good membrane permeability. One hydrophilic zwitterionic probe is able to both increase specificity and image apoptotic cells owing to its inherent chemical structure. Furthermore, we conjugated the probe with the antitumor drug gemcitabine for effective apoptosis imaging and therapeutic targeting of gastric tumors in vitro and in vivo. The novel dye-drug conjugate imaged apoptosis successfully in vitro and in vivo and restricted the growth of SGC7901 subcutaneous xenograft models. This strategy may offer the advantages of NIR apoptosis imaging probes for non-invasive tumor imaging and should provide the application for targeted drug delivery and the evaluation of therapeutic efficacy. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.11.022

文献信息

• Structure-inherent near-infrared fluorescent probe mediates apoptosis imaging and targeted drug delivery in vivo
  作者：Xianghan Zhang、Na Zhao、Bo Wang、Zuhong Tian、Yunpeng Dai、Pengbo Ning、Dan Chen

  DOI：10.1016/j.dyepig.2016.11.022

  日期：2017.3

  Imaging of tumor apoptosis can provide invaluable information in regards to drug treatment effectiveness, drug development and tumor therapeutic response. Thus, the development of apoptotic specific and sensitive targeted fluorescence probes is critically needed. In this work, we developed a novel and simple one-step synthetic method for producing monocarboxylate near-infrared cyanine dyes. The hydrophobic cationic dyes possess advantageous optical properties and good membrane permeability. One hydrophilic zwitterionic probe is able to both increase specificity and image apoptotic cells owing to its inherent chemical structure. Furthermore, we conjugated the probe with the antitumor drug gemcitabine for effective apoptosis imaging and therapeutic targeting of gastric tumors in vitro and in vivo. The novel dye-drug conjugate imaged apoptosis successfully in vitro and in vivo and restricted the growth of SGC7901 subcutaneous xenograft models. This strategy may offer the advantages of NIR apoptosis imaging probes for non-invasive tumor imaging and should provide the application for targeted drug delivery and the evaluation of therapeutic efficacy. (C) 2016 Elsevier Ltd. All rights reserved.