1-methyl-4-[(3-methyl-2(3H)-benzothiazolylidene)cyanomethyl]quinolinium iodide | 1416045-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-methyl-4-[(3-methyl-2(3H)-benzothiazolylidene)cyanomethyl]quinolinium iodide
• 英文别名: 2-(3-Methyl-1,3-benzothiazol-2-ylidene)-2-(1-methylquinolin-1-ium-4-yl)acetonitrile;iodide
• CAS: 1416045-49-2
• 化学式: C₂₀H₁₆N₃S*I
• 分子量: 457.338
• InChiKey: NLFWRCCSIJQPHC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基-2-(甲硫基)-苯并噻唑鎓碘化物(1:1) 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 1-methyl-4-[(3-methyl-2(3H)-benzothiazolylidene)cyanomethyl]quinolinium iodide
  参考文献：
  名称：

  Twisted Cyanines: A Non-Planar Fluorogenic Dye with Superior Photostability and its Use in a Protein-Based Fluoromodule

  摘要：

  The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffers from low photostability. Here, we report the synthesis of a bridge-substituted version of TO named alpha-CN-TO, where the central methine hydrogen of TO is replaced by an electron withdrawing cyano group, which was expected to decrease the susceptibility of the dye toward singlet oxygen-mediated degradation. An X-ray crystal structure shows that alpha-CN-TO is twisted drastically out of plane, in contrast to TO, which crystallizes in the planar conformation. alpha-CN-TO retains the fluorogenic behavior of the parent dye TO in viscous glycerol/water solvent, but direct irradiation and indirect bleaching studies showed that alpha-CN-TO is essentially inert to visible light and singlet oxygen. In addition, the twisted conformation of alpha-CN-TO mitigates nonspecific binding and fluorescence activation by DNA and a previously selected TO-binding protein and exhibits low background fluorescence in HeLa cell culture. alpha-CN-TO was then used to select a new protein that binds and activates fluorescence from the dye. The new alpha-CN-TO/protein fluoromodule exhibits superior photostability to an analogous TO/protein fluoromodule. These properties indicate that alpha-CN-TO will be a useful fluorogenic dye in combination with specific RNA and protein binding partners for both in vitro and cell-based applications. More broadly, structural features that promote nonplanar conformations can provide an effective method for reducing nonspecific binding of cationic dyes to nucleic acids and other biomolecules.

  DOI：

  10.1021/ja308629w