1,1',3,3,3',3'-六甲基-4,5,4',5'-二苯并吲哚二碳菁碘化物 | 56289-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,1',3,3,3',3'-六甲基-4,5,4',5'-二苯并吲哚二碳菁碘化物
• 中文别名: 1,1`,3,3,3`,3`-六甲基-4,5,4`,5`-二苯并吲哚二碳花青
• 英文名称: IR-676 iodide
• 英文别名: (2E)-1,1,3-trimethyl-2-[5-(1,1,3-trimethylbenzo[e]indol-3-ium-2-yl)penta-2,4-dienylidene]benzo[e]indole;iodide
• CAS: 56289-64-6
• 化学式: C₃₅H₃₅N₂*I
• 分子量: 610.581
• InChiKey: PXXBSYXTQAWFHV-UHFFFAOYSA-M

物化性质

• 熔点：
  270 °C (dec.)(lit.)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  38.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  6.25
• 氢给体数：
  0.0
• 氢受体数：
  1.0

安全信息

• 危险类别码：
  R42/43,R61
• 安全说明：
  S22,S36/37/39,S45,S53

反应信息

• 作为反应物：
  描述：

  1,1',3,3,3',3'-六甲基-4,5,4',5'-二苯并吲哚二碳菁碘化物 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以93%的产率得到1,1,3-trimethyl-2-[5-(1,1,3-trimethyl-2H-benzo[e]indol-2-yl)penta-2,4-dienylidene]benzo[e]indole
  参考文献：
  名称：

  氢菁：一类可以对细胞培养、组织和体内的活性氧物质进行成像的荧光传感器

  摘要：

  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。

  DOI：

  10.1002/anie.200804851

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.
• 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。