9-(2-羧基苯基)-3,6-二(二甲基氨基)呫吨鎓高氯酸盐 | 62669-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 9-(2-羧基苯基)-3,6-二(二甲基氨基)呫吨鎓高氯酸盐
• 英文名称: Tetramethylrhodamine
• 英文别名: 2-[3-(Dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate;perchloric acid
• CAS: 62669-72-1
• 化学式: C₂₄H₂₃N₂O₃*ClO₄
• 分子量: 486.909
• InChiKey: PQIPFCFHSJBFSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯酐 、 3-羟基-N,N-二甲基苯胺 在 高氯酸 作用下， 以25%的产率得到9-(2-羧基苯基)-3,6-二(二甲基氨基)呫吨鎓高氯酸盐
  参考文献：
  名称：

  Small-Molecule Labeling of Live Cell Surfaces for Three-Dimensional Super-Resolution Microscopy

  摘要：

  Precise imaging of the cell surface of fluorescently labeled bacteria requires super-resolution methods because the size-scale of these cells is on the order of the diffraction limit. In this work, we present a photocontrollable small-molecule rhodamine spirolactam emitter suitable for non-toxic and specific labeling of the outer surface of cells for three-dimensional (3D) super-resolution (SR) imaging. Conventional rhodamine spirolactams photoswitch to the emitting form with UV light; however, these wavelengths can damage cells. We extended photoswitching to visible wavelengths >400 nm by iterative synthesis and spectroscopic characterization to optimize the substitution on the spirolactam. Further, an N-hydroxysuccinimide-functionalized derivative enabled covalent labeling of amines on the surface of live Caulobacter crescentus cells. Resulting 3D SR reconstructions of the labeled cell surface reveal uniform and specific sampling with thousands of localizations per cell and excellent localization precision in x, y, and z. The distribution of cell stalk lengths (a sub-diffraction-sized cellular structure) was quantified for a mixed population of cells. Pulse-chase experiments identified sites of cell surface growth. Covalent labeling with the optimized rhodamine spirolactam label provides a general strategy to study the surfaces of living cells with high specificity and resolution down to 10-20 nm.

  DOI：

  10.1021/ja508028h