1,3,3-trimethyl-2-[7-(1,3,3-trimethyl-2H-indol-2-yl)hepta-2,4,6-trienylidene]indole | 137143-11-4

• 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: 1,3,3-trimethyl-2-[7-(1,3,3-trimethyl-2H-indol-2-yl)hepta-2,4,6-trienylidene]indole
• CAS: 137143-11-4
• 化学式: C₂₉H₃₄N₂
• 分子量: 410.602
• InChiKey: XXFVOUIBFZDUSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,3-trimethyl-2-[7-(1,3,3-trimethyl-2H-indol-2-yl)hepta-2,4,6-trienylidene]indole 在 superoxide dismutase 、 xanthine oxidase 、 黄嘌呤 作用下， 生成 1,3,3,1',3',3'-Hexamethylindotricarbocyanin
  参考文献：
  名称：

  动力学同位素效应显着提高自由基氧化剂探针的功效

  摘要：

  呼吸新鲜空气：二氢乙锭和氢菁自由基氧化剂探针的空气氧化率可以通过氘化选择性降低（见图）。由于两个反应之间的机理差异，氘代化合物和超氧化物自由基之间的反应速率降低了一个小得多的因素。在体外、细胞培养和体内，氘化探针比它们的氢类似物更有效。

  DOI：

  10.1002/anie.201002228
• 作为产物：
  描述：

  1,3,3,1',3',3'-Hexamethylindotricarbocyanin 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 1,3,3-trimethyl-2-[7-(1,3,3-trimethyl-2H-indol-2-yl)hepta-2,4,6-trienylidene]indole
  参考文献：
  名称：

  Imaging of radicals following injury or acute stress in peripheral nerves with activatable fluorescent probes

  摘要：

  Peripheral nerve injury evokes a complex cascade of chemical reactions including generation of molecular radicals. Conversely, the reactions within nerve induced by stress are difficult to directly detect or measure to establish causality. Monitoring these reactions in vivo would enable deeper understanding of the nature of the injury and healing processes. Here, we utilized near-infrared fluorescence molecular probes delivered via intraneural injection technique to enable live, in vivo imaging of tissue response associated with nerve injury and stress. These initially quenched fluorescent probes featured specific sensitivity to hydroxyl radicals and become fluorescent upon encountering reactive oxygen species (ROS). Intraneurally delivered probes demonstrated rapid activation in injured rat sciatic nerve but minimal activation in normal, uninjured nerve. In addition, these probes reported activation within sciatic nerves of living rats after a stress caused by a pinprick stimulus to the abdomen. This imaging approach was more sensitive to detecting changes within nerves due to the induced stress than other techniques to evaluate cellular and molecular changes. Specifically, neither histological analysis of the sciatic nerves, nor the expression of pain and stress associated genes in dorsal root ganglia could provide statistically significant differences between the control and stressed groups. Overall, the results demonstrate a novel imaging approach to measure ROS in addition to the impact of ROS within nerve in live animals.

  DOI：

  10.1016/j.freeradbiomed.2016.09.028

文献信息

• 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。