2-(trans-2-indol-3-yl-vinyl)-1-methyl-pyridinium; iodide | 76384-45-7

• 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: 2-(trans-2-indol-3-yl-vinyl)-1-methyl-pyridinium; iodide
• 英文别名: 2-(trans-2-Indol-3-yl-vinyl)-1-methyl-pyridinium; Jodid；3-<2-(2-Pyridyl)vinyl>indol-methoiodid；2-[(Z)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridin-1-ium iodide；3-[(Z)-2-(1-methylpyridin-1-ium-2-yl)ethenyl]-1H-indole;iodide
• CAS: 76384-45-7
• 化学式: C₁₆H₁₅N₂*I
• 分子量: 362.213
• InChiKey: HXJHUWLURCTLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  15.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(trans-2-indol-3-yl-vinyl)-1-methyl-pyridinium; iodide 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.2h， 生成 1-methyl-2-(1-methyl-3-indolylvinyl)pyridinium iodide
  参考文献：
  名称：

  Vinylogous anhydro bases of pyridylindoles

  摘要：

  DOI：

  10.1007/bf00496604
• 作为产物：
  描述：

  碳酸甲丙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 2-(trans-2-indol-3-yl-vinyl)-1-methyl-pyridinium; iodide
  参考文献：
  名称：

  Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

  摘要：

  A series of dimethine cyanine dyes, used as fluorescent probes, were synthesized under microwave irradiation, and identified by H-1 NMR, IR, elemental analysis and HRMS. The investigation of their spectral properties in phosphate-buffer saline (PBS) showed that the absorption and emission maxima of the dyes were in the region 370-480 nm and 471-569 nm, respectively. The properties of the dyes as fluorescent probes for living cells imaging and flow cytometry were investigated. The results showed that dyes 1, 2, 8 or 9 could penetrate an intact cell membrane, stained the cell nuclear and exhibited bright fluorescence. Little background interference, low cell cytotoxicity and little photobleaching were showed during the imaging tests. The dyes 1, 8 and 9 could be applied in flow cytometry and dye 1/PI, dye 8/PI or dye 9/PI couple could be proposed as double staining agents to measure sperm cell viability. Thus the dyes represented the cell-permeant fluorescent probes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.09.011

文献信息

• Bachurin; Fetisov; Afanas'ev, Doklady Chemistry, 1999, vol. 364, # 4-6, p. 41 - 44
  作者：Bachurin、Fetisov、Afanas'ev、Afanas'eva、Dubova、Yankovskaya、Mukhina

  DOI：——

  日期：——
• Akkerman; Veldstra, Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 629,646
  作者：Akkerman、Veldstra

  DOI：——

  日期：——
• Synthesis of Some 2-(3-Indolylethenyl)- and 2-(2-Pyrrylethenyl)-Pyridines and Hydrogenated Analogs
  作者：RAYMOND N. CASTLE、CHARLES W. WHITTLE

  DOI：10.1021/jo01091a005

  日期：1959.9
• Pyridinium and indole orientation determines the mitochondrial uncoupling and anti-cancer efficiency of F16
  作者：Juan Xu、Huan He、Lian-Jiao Zhou、Yu-Zhu Liu、Dong-Wei Li、Feng-Lei Jiang、Yi Liu

  DOI：10.1016/j.ejmech.2018.05.036

  日期：2018.6

  F16 is a mitochondria-targeted, broad-spectrum anticancer agent in the pre-clinic cancer therapy. Here we developed two fluorescent isomers of F16 (o-F16 and m-F16) with entirely different photophysical properties, uncoupling activity, and cytotoxicity by merely modifying the linking orientation of pyridinium and indole units. Individually, o-F16 acted as a strong uncoupler to reduce the mitochondrial respiration efficiency, while m-F16 could hardly uncouple the mitochondrial respiration due to its poor proton dissociation capability. Owing to their intrinsic fluorescence, o-F16 and m-F16 could specifically image mitochondria in the green and red channel, respectively. This work could provide useful information for the development of uncouplers and design of mitochondrial-targeted drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Derivatives of indole and method for the production thereof
  申请人：HOFFMANN LA ROCHE

  公开号：US02695290A1

  公开（公告）日：1954-11-23