2-[2-[4-(1-pyrrolidinyl)phenyl]ethenyl]-1,3,3-trimethyl-3H-indolium iodide | 25850-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-[2-[4-(1-pyrrolidinyl)phenyl]ethenyl]-1,3,3-trimethyl-3H-indolium iodide
• 英文别名: 1,3,3-Trimethyl-2-[2-(4-pyrrolidin-1-ylphenyl)ethenyl]indol-1-ium;iodide；1,3,3-trimethyl-2-[2-(4-pyrrolidin-1-ylphenyl)ethenyl]indol-1-ium;iodide
• CAS: 25850-25-3
• 化学式: C₂₃H₂₇N₂*I
• 分子量: 458.385
• InChiKey: BYUCENOZTGVBAU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁酮 在 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 2-[2-[4-(1-pyrrolidinyl)phenyl]ethenyl]-1,3,3-trimethyl-3H-indolium iodide
  参考文献：
  名称：

  2-Styrylindolium based fluorescent probes visualize neurofibrillary tangles in Alzheimer’s disease

  摘要：

  We evaluated 2-styrylindolium derivatives (6-11) as novel and selective probes for neurofibrillary tangles (NFTs) on brain sections of AD patients. The staining experiments indicated that these compounds may bind selectively to NFTs in the presence of beta-amyloid (A beta) plaques. Cell free binding assays confirmed that 2-[2-[4-(1-pyrrolidinyl) phenyl]ethenyl]-1,3,3-trimethyl-3H-indolium iodide (9) and 2-[2-[4-(diethylamino) phenyl] ethenyl]-1-butyl-3,3-dimethyl-3H-indolium iodide (11) display excellent affinities to Tau-aggregates (IC50 values of 5.1 and 1.4 nM, respectively) in the displacement of Thiazin Red R. These probes have good solubility in distilled water and low or no cytotoxicity in zebrafish embryo and liver hepatocellular carcinoma cell assays. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.109

文献信息

• OFF/ON Red-Emitting Fluorescent Probes for Casein Recognition and Quantification Based on Indolium Derivatives
  作者：Wei Yang、Chunlin Liu、Qingyun Gao、Jinya Du、Ping Shen、Changying Yang

  DOI：10.1007/s10895-016-1967-0

  日期：2017.1

  (H1 - H5) were synthesized for the determination of proteins. H3, a sensitive red-emitting fluorescent probe, was found for the discrimination of hydrophobic proteins from hydrophilic. The OFF - ON fluorescence switch of H3 was caused by the formation of twisted intramolecular charge-transfer (TICT) state when it combined with hydrophobic proteins in aqueous buffer. There was a good linear relationship

  合成了含有不同电子供体基团（H1-H5）的5种2、3、3-三甲基-3H-吲哚衍生物，用于蛋白质的测定。发现了H3，一种敏感的发红光荧光探针，用于区分疏水性蛋白质和亲水性蛋白质。H3的OFF-ON荧光开关是由于在水性缓冲液中与疏水蛋白结合时形成的扭曲分子内电荷转移（TICT）状态引起的。H3的发射强度与酪蛋白浓度（r = 0.9989）。在此基础上，开发了一种新型酪蛋白定量测定方法，并将该方法用于奶粉样品中酪蛋白的测定。成功地，结果与Biuret方法非常吻合。此外，由于三种酪蛋白组分（α-，β-和κ-酪蛋白）与H3探针的结合常数相差很大，因此建立了一种简单而灵敏的方法来区分和定量三种酪蛋白组分。
• 2-Styrylindolium based fluorescent probes visualize neurofibrillary tangles in Alzheimer’s disease
  作者：Jiamin Gu、Upendra Rao Anumala、Fabio Lo Monte、Thomas Kramer、Roland Heyny von Haußen、Jana Hölzer、Valérie Goetschy-Meyer、Gerhard Mall、Ingrid Hilger、Christian Czech、Boris Schmidt

  DOI：10.1016/j.bmcl.2012.09.109

  日期：2012.12

  We evaluated 2-styrylindolium derivatives (6-11) as novel and selective probes for neurofibrillary tangles (NFTs) on brain sections of AD patients. The staining experiments indicated that these compounds may bind selectively to NFTs in the presence of beta-amyloid (A beta) plaques. Cell free binding assays confirmed that 2-[2-[4-(1-pyrrolidinyl) phenyl]ethenyl]-1,3,3-trimethyl-3H-indolium iodide (9) and 2-[2-[4-(diethylamino) phenyl] ethenyl]-1-butyl-3,3-dimethyl-3H-indolium iodide (11) display excellent affinities to Tau-aggregates (IC50 values of 5.1 and 1.4 nM, respectively) in the displacement of Thiazin Red R. These probes have good solubility in distilled water and low or no cytotoxicity in zebrafish embryo and liver hepatocellular carcinoma cell assays. (C) 2012 Elsevier Ltd. All rights reserved.