5-carboxy-1-(p-carboxybenzyl)-2,3,3-trimethylindolenium bromide | 1211408-63-7

• 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: 5-carboxy-1-(p-carboxybenzyl)-2,3,3-trimethylindolenium bromide
• 英文别名: 5-carboxy-1-(4-carboxybenzyl)-2,3,3-trimethyl-3H-indol-1-ium bromide
• CAS: 1211408-63-7
• 化学式: Br*C₂₀H₂₀NO₄
• 分子量: 418.287
• InChiKey: CMZVNGZTUQJULT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.61
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-carboxy-1-(p-carboxybenzyl)-2,3,3-trimethylindolenium bromide 、 2-氯-1-甲酰-3-羟基亚甲基环己烯 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 反应 0.5h， 以100 mg的产率得到2-[4'-chloro-7'-(1''-(p-carboxybenzyl)-3'',3''-dimethylindolenine)-3',5'-trimethylenehepta-trien-1-yl]-1-(p-carboxybenzyl)-3,3-dimethylindolenium bromide
  参考文献：
  名称：

  Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes

  摘要：

  Reactive oxygen species (ROS) operate as signaling molecules under various physiological conditions, and overproduction of ROS is involved in the pathogenesis of many diseases. Therefore, fluorescent probes for visualizing ROS are promising tools with which to uncover the molecular mechanisms of physiological and pathological processes and might also be useful for diagnosis. Here we describe a novel fluorescence probe, FOSCY-1, operating in the physiologically favorable near-infrared region. The probe consists of two differentially ROS-reactive cyanine dyes connected by a linker; reaction of the more susceptible dye with ROS releases intramolecular fluorescence quenching of the less susceptible dye. We successfully applied this probe to detect ROS produced by HL60 cells and porcine neutrophils and for imaging oxidative stress in a mouse model of peritonitis.

  DOI：

  10.1021/ja910090v
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 4-肼基苯甲酸 在 sodium acetate 、 溶剂黄146 作用下， 以 邻二氯苯 为溶剂， 反应 8.5h， 生成 5-carboxy-1-(p-carboxybenzyl)-2,3,3-trimethylindolenium bromide
  参考文献：
  名称：

  Near-infrared heptamethine cyanine dye-based nanoscale coordination polymers with intrinsic nucleus-targeting for low temperature photothermal therapy

  摘要：

  Effective photothermal therapy (PTT) under low temperature (< 50 degrees C) and power density (< 0.4 W/cm(2)) avoiding the damage of skin and normal organs. Here, we report a novel heptamethine cyanine dye-based nanoscale coordination polymer (NCP), Hf-HI-4COOH, as an exceptionally effective photosensitizer for nucleus-targeting low temperature PTT. Hf-HI-4COOH shows strong near-infrared absorption and high photothermal conversion efficiency (39.51 %). Further, it exhibits intrinsic nucleus-targeting property and cell inhibition under low power density in vitro. Moreover, the long blood circulation, high tumor accumulation, and nucleus-targeting contribute to significant inhibition of breast tumors in tumor-bearing mice under low temperature (48 degrees C) and power density (0.3 W/cm(2)) without obvious toxicity. In general, we establish a nucleus-targeting Hf-HI-4COOH for enhanced PTT with low temperature and power density. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.nantod.2020.100910