2-[3-(1,3-dihydro-3,3-dimethyl-1-butyl-2H-indol-2-yliden)-1-propen-1-yl]-3,3-dimethyl-1-butyl-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: 2-[3-(1,3-dihydro-3,3-dimethyl-1-butyl-2H-indol-2-yliden)-1-propen-1-yl]-3,3-dimethyl-1-butyl-indolium iodide
• 英文别名: 1-Butyl-2-[3-(1-butyl-3,3-dimethylindol-1-ium-2-yl)prop-2-enylidene]-3,3-dimethylindole;iodide；1-butyl-2-[3-(1-butyl-3,3-dimethylindol-1-ium-2-yl)prop-2-enylidene]-3,3-dimethylindole;iodide
• 化学式: C₃₁H₄₁N₂*I
• 分子量: 568.584
• InChiKey: CVTQMCMIKOZBTI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[3-(1,3-dihydro-3,3-dimethyl-1-butyl-2H-indol-2-yliden)-1-propen-1-yl]-3,3-dimethyl-1-butyl-indolium iodide 、 以 N-甲基吡咯烷酮 为溶剂， 反应 1.0h， 以85%的产率得到
  参考文献：
  名称：

  TWI518143

  摘要：

  公开号：
• 作为产物：
  描述：

  苯肼,盐酸盐 在 乙酸酐 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 72.5h， 生成 2-[3-(1,3-dihydro-3,3-dimethyl-1-butyl-2H-indol-2-yliden)-1-propen-1-yl]-3,3-dimethyl-1-butyl-indolium iodide
  参考文献：
  名称：

  Selective G-Quadruplex DNA Recognition by a New Class of Designed Cyanines

  摘要：

  多种菁染料作为DNA染料和传感器具有多功能性和灵敏性，并已通过结构修饰，以序列依赖的方式结合于DNA小沟。同样，我们正在开发一套新的菁染料，这些染料被设计用于高度选择性地结合DNA G-四链体，而对DNA双链的结合力较弱。系统地合成了结构类似的三甲川菁染料并评估了其对四链体的靶向作用。结果显示，增强四链体结合和特异性对多甲川链长度、杂环结构和化合物的固有电荷非常敏感。生物物理实验表明，这些化合物对四链体结合表现出显著的选择性，更偏好于平行链四链体，如cMYC。核磁共振研究揭示了主要通过末端堆积模式结合，表面等离子体共振研究显示最强的化合物主要的解离常数值低于100 nM，而对双链体的结合力几乎弱了100倍。这些新设计的三甲川菁染料对四链体的高度选择性以及它们区分不同四链体的能力是非常有前景的特性，有望开发它们作为体内靶向四链体的新型探针。

  DOI：

  10.3390/molecules181113588

文献信息

• Design, Synthesis and Biological Evaluation of Trimethine Cyanine Dyes as Fluorescent Probes for the Detection of Tau Fibrils in Alzheimer’s Disease Brain and Olfactory Epithelium
  作者：Jiamin Gu、Upendra Rao Anumala、Roland Heyny-von Haußen、Jana Hölzer、Valérie Goetschy-Meyer、Gerhard Mall、Ingrid Hilger、Christian Czech、Boris Schmidt

  DOI：10.1002/cmdc.201300090

  日期：2013.6

  Shedding light on grey matter: Fluorescent trimethine cyanines were evaluated as imaging probes for neurofibrillary tangles in post‐mortem brain sections of Alzheimer's disease patients. These probes bind to neurofibrillary tangles with high contrast and selectivity over amyloid β plaques.

  灰质上的光芒：荧光三甲胺花青被评估为阿尔茨海默氏病患者死后脑切片中神经原纤维缠结的成像探针。这些探针以比淀粉样蛋白β斑块更高的对比度和选择性与神经原纤维缠结结合。
• COMPOUNDS FOR THE DIAGNOSIS OF NEURODEGENERATIVE DISORDERS ON THE OLFACTORY EPITHELIUM
  申请人：Schmidt Boris

  公开号：US20130287700A1

  公开（公告）日：2013-10-31

  Subject of the present invention are compounds with high affinity for the Aβ protein, α-synuclein or for Tau-PHF aggregates, which are suitable as preferably fluorescent probes for the in vivo diagnosis of neurodegenerative disorders like e.g. Alzheimer's disease and Parkinson's disease. The compounds are characterized by suitable physicochemical properties (excitation wavelength, emission wavelength, Stokes shift, extinction) as well as a high affinity and selectivity for the target proteins.

  本发明的主题是具有高亲和力的化合物，用于Aβ蛋白、α-突触核蛋白或Tau-PHF聚集物，适用于作为体内诊断神经退行性疾病（如阿尔茨海默病和帕金森病）的首选荧光探针。这些化合物具有适当的物理化学性质（激发波长、发射波长、斯托克斯位移、消光），以及对目标蛋白的高亲和力和选择性。
• Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents
  作者：Sarmistha Halder Sinha、Eric A. Owens、You Feng、Yutao Yang、Yan Xie、Yaping Tu、Maged Henary、Yujun George Zheng

  DOI：10.1016/j.ejmech.2012.06.017

  日期：2012.8

  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.
• External iodine atoms influence over the intersystem crossing rate of cyanine iodide ion pair in benzene solution
  作者：Bjorn Sauerwein、Gary B. Schuster

  DOI：10.1021/j100158a006

  日期：1991.3

  The photochemical and photophysical properties of N,N'-dibutyltetramethylindocarbocyanine iodide [TMIC]Bu+I-} in benzene solution were examined by absorption spectroscopy and flash photolysis on a picosecond time scale. In benzene solution, the dye iodide exists nearly exclusively as an ion pair. Under these conditions the absorption spectrum of the cyanine dye is perturbed by the iodide ion by a dispersion interaction. Irradiation of the cyanine iodide ion pair generates the triplet-state cyanine.
• VERBINDUNGEN FÜR DIE DIAGNOSTIK NEURODEGENERATIVER ERKRANKUNGEN AN DER RETINA
  申请人：Technische Universität Darmstadt

  公开号：EP2619590A2

  公开（公告）日：2013-07-31