9-(2-羧基苯基)-3,6-二(二乙基氨基)呫吨鎓高氯酸盐 | 23857-51-4

• 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(二乙基氨基)呫吨鎓高氯酸盐
• 英文名称: rhodamine B perchlorate
• 英文别名: rhodamine B；2-[3-(Diethylamino)-6-diethylazaniumylidenexanthen-9-yl]benzoate;perchloric acid
• CAS: 23857-51-4
• 化学式: C₂₈H₃₁N₂O₃*ClO₄
• 分子量: 543.016
• InChiKey: GZFMWASBMSLFDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(2-羧基苯基)-3,6-二(二乙基氨基)呫吨鎓高氯酸盐 在 三(3,6-二氧杂庚基)胺 、 palladium diacetate 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成
  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
• 作为产物：
  描述：

  苯酐 、 3-羟基-N,N-二乙基苯胺 在 高氯酸 作用下， 以35%的产率得到9-(2-羧基苯基)-3,6-二(二乙基氨基)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

文献信息

• ELECTRO-SPUN FIBERS AND APPLICATIONS THEREFOR
  申请人：The Ohio State University Research Foundation

  公开号：EP2329064A1

  公开（公告）日：2011-06-08
• ELECTRO-SPUN FIBERS AND APPLICATIONS THEREFORE
  申请人：Olesik Susan V.

  公开号：US20110214487A1

  公开（公告）日：2011-09-08

  A supported nanofiber medium useful for segregating chemical species is provided by selecting a polymer, selecting a substrate; and electrospinning the polymer to form a nanofiber medium on the supporting substrate. When the substrate is a planar surface, the nanofiber medium will be a mat suitable for conducting chromatographic separation. When the substrate is a filament, the nanofiber medium is an annular mat suitable for solid phase microextraction. The nanofiber media formed may be selectively cross-linked and at least partially carbonized to carbon nanofibers. The nanofiber medium is supported on the substrate without the use of binder material.
• ELECTRO-SPUN FIBERS AND APPLICATIONS THEREOF
  申请人：THE OHIO STATE UNIVERSITY RESEARCH FOUNDATION

  公开号：US20170016144A1

  公开（公告）日：2017-01-19

  A supported nanofiber medium useful for segregating chemical species is provided by selecting a polymer, selecting a substrate; and electrospinning the polymer to form a nanofiber medium on the supporting substrate. When the substrate is a planar surface, the nanofiber medium will be a mat suitable for conducting chromatographic separation. When the substrate is a filament, the nanofiber medium is an annular mat suitable for solid phase microextraction. The nanofiber media formed may be selectively cross-linked and at least partially carbonized to carbon nanofibers. The nanofiber medium is supported on the substrate without the use of binder material.
• US8568587B2
  申请人：——

  公开号：US8568587B2

  公开（公告）日：2013-10-29
• [EN] ELECTRO-SPUN FIBERS AND APPLICATIONS THEREFOR<br/>[FR] FIBRES OBTENUES PAR FILAGE ÉLECTRIQUE ET APPLICATIONS DE CELLES-CI
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2010030900A1

  公开（公告）日：2010-03-18

  A supported nanofiber medium useful for segregating chemical species is provided by selecting a polymer, selecting a substrate; and electrospinning the polymer to form a nanofiber medium on the supporting substrate. When the substrate is a planar surface, the nanofiber medium will be a mat suitable for conducting chromatographic separation. When the substrate is a filament, the nanofiber medium is an annular mat suitable for solid phase microextraction. The nanofiber media formed may be selectively cross-linked and at least partially carbonized to carbon nanofibers. The nanofiber medium is supported on the substrate without the use of binder material.