2-((1E,3Z,5E)-3-bromo-5-(1,1,3-trimethyl-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1,1,3-trimethyl-1H-benzo[e]indol-3-ium iodide | 36954-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((1E,3Z,5E)-3-bromo-5-(1,1,3-trimethyl-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1,1,3-trimethyl-1H-benzo[e]indol-3-ium iodide
• 英文别名: (2E)-2-[(2Z,4E)-3-bromo-5-(1,1,3-trimethylbenzo[e]indol-3-ium-2-yl)penta-2,4-dienylidene]-1,1,3-trimethylbenzo[e]indole;iodide
• CAS: 36954-18-4
• 化学式: C₃₅H₃₄BrN₂*I
• 分子量: 689.477
• InChiKey: YGOTXSOMNHYFNH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 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 sodium acetate 作用下， 以 乙酸酐 、 乙腈 为溶剂， 生成 2-((1E,3Z,5E)-3-bromo-5-(1,1,3-trimethyl-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1,1,3-trimethyl-1H-benzo[e]indol-3-ium iodide
  参考文献：
  名称：

  五甲叉菁花青染料在长波长可见光照射下的氧化氧化作用

  摘要：

  这里，我们报告七种对称羰花青染料，其中两个氮取代的苯并〔合成ë ]吲哚鎓环通过五甲桥，其接合内消旋与氯或溴与氢取代。苯并[ e ]吲哚的杂原子被苯丙基，甲基或阳离子季铵基团改性。在含有微摩尔浓度的卤化染料的反应中，在575、588、623或700 nm处进行辐照可对质粒DNA进行良好的光裂解。紫外可见光谱表明，花青素呈H聚集和单体形式。清道夫实验指出单重态氧和羟基自由基参与DNA光裂解。

  DOI：

  10.1016/j.bmcl.2013.11.035

文献信息

• Oxidative cleavage of DNA by pentamethine carbocyanine dyes irradiated with long-wavelength visible light
  作者：Carla T. Mapp、Eric A. Owens、Maged Henary、Kathryn B. Grant

  DOI：10.1016/j.bmcl.2013.11.035

  日期：2014.1

  containing micro molar concentrations of halogenated dye, irradiation at 575, 588, 623, or 700 nm produces good photocleavage of plasmid DNA. UV–visible spectra show that the carbocyanines are in their H-aggregated and monomeric forms. Scavenger experiments point to the involvement of singlet oxygen and hydroxyl radicals in DNA photocleavage.

  这里，我们报告七种对称羰花青染料，其中两个氮取代的苯并〔合成ë ]吲哚鎓环通过五甲桥，其接合内消旋与氯或溴与氢取代。苯并[ e ]吲哚的杂原子被苯丙基，甲基或阳离子季铵基团改性。在含有微摩尔浓度的卤化染料的反应中，在575、588、623或700 nm处进行辐照可对质粒DNA进行良好的光裂解。紫外可见光谱表明，花青素呈H聚集和单体形式。清道夫实验指出单重态氧和羟基自由基参与DNA光裂解。
• Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake
  作者：Eric A. Owens、Hoon Hyun、Joseph G. Tawney、Hak Soo Choi、Maged Henary

  DOI：10.1021/acs.jmedchem.5b00475

  日期：2015.5.28

  Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical, properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the,delineation of delicate glands.