1-ethyl-2-((1E,3E)-3-(1-ethyl-3,3-dimethylindolin-2-ylidene)prop-1-en-1-yl)-3,3-dimethyl-3H-indolium iodide

• 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-ethyl-2-((1E,3E)-3-(1-ethyl-3,3-dimethylindolin-2-ylidene)prop-1-en-1-yl)-3,3-dimethyl-3H-indolium iodide
• 英文别名: 1,1'-diethyl-3,3,3',3'-tetramethylindocarbocyanine iodide；1,1'-diethyl-3,3,3',3'-tetramethylindocarbocyanine；E-14
• 化学式: C27H33IN2
• 分子量: 512.5
• InChiKey: LGRNGKUSEZTBMB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  1-乙基-2,3,3-三甲基吲哚鎓碘化物 、 原甲酸三乙酯 在 乙酸酐 作用下， 反应 2.0h， 以77%的产率得到1-ethyl-2-((1E,3E)-3-(1-ethyl-3,3-dimethylindolin-2-ylidene)prop-1-en-1-yl)-3,3-dimethyl-3H-indolium iodide
  参考文献：
  名称：

  Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents

  摘要：

  Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.017

文献信息

• Synthesis and physical performance of indole and benzimidazole cyanine dyes
  作者：Zheng-Hong Peng、Li Qun、Xiang-Feng Zhou、Suzanne Carroll、Herman. J. Geise、Bi-xian Peng、Roger Dommisse、Robert Carleer

  DOI：10.1039/jm9960600559

  日期：——

  Nine indole and benzimidazole cyanine dyes, used as green-sensitizing dyes in photographic emulsions, are synthesized. The compounds are characterized from mass spectrometric and NMR spectroscopic data, and elemental analysis. FAB mass spectrometry proved to be an efficient method for determining the structure of the compounds. From UV–VIS data of the compounds the sensitizing properties of the cyanine dyes are predicted. The reflection spectrum of Gs2-9 coated in photographic emulsions showed J-aggregation behaviour at λ= 560 nm. Unsymmetric benzimidazole–indole cyanine dyes showed good to excellent green sensitizing properties in photographic emulsions, whereas symmetric indole cyanine dyes showed heavy residual colour and no sensitizing properties.

  合成了九种吲哚和苯并咪唑青链染料，作为摄影乳剂中的绿敏化染料。通过质谱、核磁共振光谱数据和元素分析对这些化合物进行了表征。FAB质谱证明是一种有效的确定化合物结构的方法。根据化合物的UV–VIS数据，可以预测青链染料的敏化特性。涂覆在摄影乳剂中的Gs2-9的反射光谱在λ= 560 nm处表现出J聚集行为。不对称的苯并咪唑–吲哚青链染料在摄影乳剂中表现出良好至优异的绿敏化特性，而对称的吲哚青链染料则显示出严重的残留颜色且没有敏化特性。
• Survey, fluorescence spectra, and solubility of liquid cyanine dyes
  作者：Masaki Matsui、Takaya Yamamoto、Yasuhiro Kubota、Kazumasa Funabiki

  DOI：10.1039/c6nj02160c

  日期：——

  synthesized four liquid cyanine dyes, namely N,N′-didodecyl 44,N,N′-dioctadecyl indolenium 45,N,N′-bis(2,5,8-trioxa-10-octadecanyl)benzoxazolium 50 and benzothiazolium 51, which have a bis(perfluorobutylsulfonyl)imide anion. In the neat form, these liquid dyes exhibit more intense fluorescence at −196 °C than at 25 °C. The liquid N,N′-dialkylated indolenium derivatives 44 and 45 exhibited larger solubility

  我们合成了四种液体花青染料，分别是N，N'-二十二烷基44，N，N'-二十八烷基吲哚45，N，N'-双（2,5,8-三恶唑-10-十八烷基）苯并恶唑50和苯并噻唑鎓51，其具有双（全氟丁基磺酰基）酰亚胺阴离子。以纯净的形式，这些液体染料在-196°C处比在25°C下表现出更强的荧光。液态的N，N'-二烷基化的吲哚衍生物44和45在己烷中的溶解度大于相应的固态衍生物。另外，液态氮，N′-双（2,5,8-三氧杂-10-十八烷基）苯并恶唑鎓和苯并噻唑鎓衍生物50和51比相应的固体衍生物更易溶于丙醇。
• 着色組成物、カラーフィルタ用着色組成物、および、カラーフィルタ
  申请人：東洋インキＳＣホールディングス株式会社

  公开号：JP2015137300A

  公开（公告）日：2015-07-30

  【課題】溶剤に可溶でかつ、鮮明な赤色染料として利用可能な造塩化合物を用いた着色組成物、カラーフィルタ用途として使用する場合に、明度、耐熱性、コントラスト比に優れたカラーフィルタ用着色組成物、並びに塗膜への異物発生もないカラーフィルタの提供。【解決手段】一般式（１−１）で表されるカチオン性シアニン系染料の造塩化合物、及び有機溶剤を含有する着色組成物。[Ａ1及びＡ2は各々独立に、−ＣＲ12（Ｒ13）−、又は、−Ｓ−；Ｒ1〜Ｒ11は各々独立に、Ｈ、置換もしくは無置換のアルキル基等；Ｒ12及びＲ13は各々独立に、置換もしくは無置換のアルキル基等；Anion-は特定の硫酸アニオン]【選択図】なし

  使用可溶于溶剂且作为鲜明红色染料的造盐化合物的着色组合物，用于彩色滤光片，具有优异的亮度、耐热性和对比度，以及无异物生成在涂层上的彩色滤光片的提供。含有由通式（1-1）表示的阳离子性吖啶系染料的造盐化合物和有机溶剂的着色组合物。【A1和A2各自独立表示- CR12（R13）-或-S-；R1〜R11各自独立表示H，取代或未取代的烷基等；R12和R13各自独立表示取代或未取代的烷基等；Anion-表示特定的硫酸根阴离子】。【选择图】无
• A new Vilsmeier-type reaction for one-pot synthesis of pH sensitive fluorescent cyanine dyes
  作者：Reda M. El-Shishtawy、Paulo Almeida

  DOI：10.1016/j.tet.2006.05.063

  日期：2006.8

  A new Vilsmeier-type reaction is suggested for the synthesis of novel indocarbocyanine pH sensors, which are fluorescent when protonated but nonfluorescent upon proton abstraction. These sensors show significant ratiometric UV–visible as well as fluorescence spectral changes upon subtle variation of pHs with pKa values near neutral.

  建议使用新的Vilsmeier型反应来合成新型吲哚并花菁pH传感器，该传感器在质子化时发出荧光，而在质子提取时发出荧光。当pH值的微妙变化（p K a值接近中性）时，这些传感器显示出明显的比例紫外线可见光以及荧光光谱变化。
• Hydrocyanines: A Class of Fluorescent Sensors That Can Image Reactive Oxygen Species in Cell Culture, Tissue, and In Vivo
  作者：Kousik Kundu、Sarah F. Knight、Nick Willett、Sungmun Lee、W. Robert Taylor、Niren Murthy

  DOI：10.1002/anie.200804851

  日期：2009.1.2

  Accurate and tunable: The title compounds can detect reactive oxygen species (ROS) in cell culture, tissue explants, and for the first time in vivo. The hydrocyanines are synthesized by reduction of the cyanine dyes with NaBH4. They can accurately detect nanomolar levels of ROS, have excellent stability against autoxidation, and have tunable emission wavelengths in the range 560–830 nm.

  准确且可调：标题化合物可以检测细胞培养物、组织外植体中的活性氧 (ROS)，这是首次在体内检测。氢花青是通过用 NaBH 4还原花青染料来合成的。它们可以准确检测纳摩尔水平的 ROS，对自氧化具有出色的稳定性，并且具有 560-830 nm 范围内的可调发射波长。