1H-苯并[e]吲哚正离子,3-乙基-2-[3-(3-乙基-1,3-二氢-1,1-二甲基-2H-苯并[e]吲哚-2-亚基)-1-丙烯基]-1,1-二甲基-,碘化 | 186818-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1H-苯并[e]吲哚正离子,3-乙基-2-[3-(3-乙基-1,3-二氢-1,1-二甲基-2H-苯并[e]吲哚-2-亚基)-1-丙烯基]-1,1-二甲基-,碘化
• 英文名称: 3-ethyl-2-((1E,3E)-3-(3-ethyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)prop-1-en-1-yl)-1,1-dimethyl-1H-benzo[e]indol-3-ium iodide
• 英文别名: E-5；3-ethyl-2-[(E)-3-(3-ethyl-1,1-dimethylbenzo[e]indol-3-ium-2-yl)prop-2-enylidene]-1,1-dimethylbenzo[e]indole;iodide
• CAS: 186818-80-4
• 化学式: C₃₅H₃₇N₂*I
• 分子量: 612.597
• InChiKey: RDCWRZDJSZMFQA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,1,2-三甲基苯-1H-苯并[e]吲哚 在 乙酸酐 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 1H-苯并[e]吲哚正离子,3-乙基-2-[3-(3-乙基-1,3-二氢-1,1-二甲基-2H-苯并[e]吲哚-2-亚基)-1-丙烯基]-1,1-二甲基-,碘化
  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 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.