1,1,2-Trimethyl-3-pent-4-ynyl-benzo[e]indol-3-ium iodide | 1354932-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1,2-Trimethyl-3-pent-4-ynyl-benzo[e]indol-3-ium iodide
• 英文别名: 1,1,2-trimethyl-3-pent-4-ynylbenzo[e]indol-3-ium;iodide
• CAS: 1354932-45-8
• 化学式: C₂₀H₂₂N*I
• 分子量: 403.306
• InChiKey: QIYYGEMDTWHZPO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1,2-Trimethyl-3-pent-4-ynyl-benzo[e]indol-3-ium iodide 在 哌啶 、 三溴化硼 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  TME-targeting theranostic agent uses NIR tracking for tumor diagnosis and surgical resection and acts as chemotherapeutic showing enhanced efficiency and minimal toxicity

  摘要：

  理由：肿瘤微环境（TME）的精确诊断和有效治疗仍然是一个挑战。目前已报道用于监测原发性肿瘤的荧光示踪剂；然而，他们在手术过程中实时准确描绘肿瘤面临挑战，包括背景干扰和肿瘤部位成像试剂积累不足。此外，虽然天然产物鬼臼毒素（PPT）具有强大而广泛的抗肿瘤活性，但PPT的肿瘤靶点特异性差和毒性大极大限制了其临床应用。

  DOI：

  10.7150/thno.68074
• 作为产物：
  描述：

  1,1,2-三甲基苯-1H-苯并[e]吲哚 、 5-氯戊炔 在 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以69%的产率得到1,1,2-Trimethyl-3-pent-4-ynyl-benzo[e]indol-3-ium iodide
  参考文献：
  名称：

  TME-targeting theranostic agent uses NIR tracking for tumor diagnosis and surgical resection and acts as chemotherapeutic showing enhanced efficiency and minimal toxicity

  摘要：

  理由：肿瘤微环境（TME）的精确诊断和有效治疗仍然是一个挑战。目前已报道用于监测原发性肿瘤的荧光示踪剂；然而，他们在手术过程中实时准确描绘肿瘤面临挑战，包括背景干扰和肿瘤部位成像试剂积累不足。此外，虽然天然产物鬼臼毒素（PPT）具有强大而广泛的抗肿瘤活性，但PPT的肿瘤靶点特异性差和毒性大极大限制了其临床应用。

  DOI：

  10.7150/thno.68074

文献信息

• Efficient reverse click labeling of azide oligonucleotides with multiple alkynyl Cy-Dyes applied to the synthesis of HyBeacon probes for genetic analysis
  作者：Marta Gerowska、Lucy Hall、James Richardson、Montserrat Shelbourne、Tom Brown

  DOI：10.1016/j.tet.2011.11.041

  日期：2012.1

  A convenient method of oligonucleotide labeling using click chemistry has been developed. A 2'-mesyloxyethyl ribothymidine phosphoramidite monomer was incorporated into DNA at several loci during solid phase oligonucleotide synthesis and converted to 2'-azidoethyl ribothymidine in high yield on the synthesis resin. The resultant azide oligonucleotides were doubly and triply labeled with alkynemodified cyanine dyes and their biophysical properties were studied. The influence of the dye structures and method of labeling on the fluorescence properties of the DNA probes is discussed and compared with a standard labeling method using active esters of Cy-Dyes. (C) 2011 Elsevier Ltd. All rights reserved.
• MemBright: A Family of Fluorescent Membrane Probes for Advanced Cellular Imaging and Neuroscience
  作者：Mayeul Collot、Pichandi Ashokkumar、Halina Anton、Emmanuel Boutant、Orestis Faklaris、Thierry Galli、Yves Mély、Lydia Danglot、Andrey S. Klymchenko

  DOI：10.1016/j.chembiol.2019.01.009

  日期：2019.4

  The proper staining of the plasma membrane (PM) is critical in bioimaging as it delimits the cell. Herein, we developed MemBright, a family of six cyanine-based fluorescent turn-on PM probes that emit from orange to near infrared when reaching the PM, and enable homogeneous and selective PM staining with excellent contrast in mono- and two-photon microscopy. These probes are compatible with long-term live-cell imaging and immunostaining. Moreover, MemBright label neurons in a brighter manner than surrounding cells, allowing identification of neurons in acute brain tissue sections and neuromuscular junctions without any use of transfection or transgenic animals. In addition, MemBright probes were used in super-resolution imaging to unravel the neck of dendritic spines. 3D multicolor dSTORM in combination with immunostaining revealed en-passant synapse displaying endogenous glutamate receptors clustered at the axonal-dendritic contact site. MemBright probes thus constitute a universal toolkit for cell biology and neuroscience biomembrane imaging with a variety of microscopy techniques.
• Redox-Activatable Theranostic Co-Prodrug for Precise Tumor Diagnosis and Selective Combination Chemotherapy
  作者：Jianqiang Qian、Zhongyuan Xu、Chi Meng、Yun Liu、Hongmei Wu、Yunyun Wang、Jinxian Yang、Hongwei Zheng、Fansheng Ran、Gong-Qing Liu、Yong Ling

  DOI：10.1021/acs.jmedchem.2c00130

  日期：2022.8.11