5,5'-dimethoxy-1,1',3,3,3',3'-hexamethylindodicarbocyanine iodide | 1200441-59-3

• 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: 5,5'-dimethoxy-1,1',3,3,3',3'-hexamethylindodicarbocyanine iodide
• 英文别名: 5-methoxy-2-[5-(5-methoxy-1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]-1,3,3-trimethylindole;iodide
• CAS: 1200441-59-3
• 化学式: C₂₉H₃₅N₂O₂*I
• 分子量: 570.514
• InChiKey: GRHCPAASZFEDFV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-methoxy-1,2,3,3-tetramethyl-3H-indolium iodide 、 1-anilino-3-phenyliminopropene 在 sodium acetate 、 乙酸酐 作用下， 反应 4.0h， 以75%的产率得到5,5'-dimethoxy-1,1',3,3,3',3'-hexamethylindodicarbocyanine iodide
  参考文献：
  名称：

  Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

  摘要：

  Our initial efforts to prepare tissue-specific near infrared (NIR) fluorescent compounds generated successful correlation between physicochemical, properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.

  DOI：

  10.1021/acs.jmedchem.6b00038

文献信息

• Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes
  作者：Daihi Oushiki、Hirotatsu Kojima、Takuya Terai、Makoto Arita、Kenjiro Hanaoka、Yasuteru Urano、Tetsuo Nagano

  DOI：10.1021/ja910090v

  日期：2010.3.3

  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.
• Near-Infrared Illumination of Native Tissues for Image-Guided Surgery
  作者：Eric A. Owens、Hoon Hyun、Tyler L. Dost、Jeong Heon Lee、GwangLi Park、Dang Huan Pham、Min Ho Park、Hak Soo Choi、Maged Henary

  DOI：10.1021/acs.jmedchem.6b00038

  日期：2016.6.9

  Our initial efforts to prepare tissue-specific near infrared (NIR) fluorescent compounds generated successful correlation between physicochemical, properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.