N,N'-bis(6-O-(carboxymethyl)fluorescein ethyl ester)-L-cystine bis-t-butyl ester | 947509-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N,N'-bis(6-O-(carboxymethyl)fluorescein ethyl ester)-L-cystine bis-t-butyl ester
• CAS: 947509-71-9
• 化学式: C₆₂H₆₀N₂O₁₆S₂
• 分子量: 1153.29
• InChiKey: HOZYOPQXTLYLPI-CRKOEVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.29
• 重原子数：
  82.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  242.28
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (4-((5-nitropyridin-2-yl)disulfaneyl)butyl)triphenylphosphonium bromide 、 N,N'-bis(6-O-(carboxymethyl)fluorescein ethyl ester)-L-cystine bis-t-butyl ester 在 DL-dithiothreitol 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.75h， 以53%的产率得到
  参考文献：
  名称：

  A “Ready-To-Use” fluorescent-labelled-cysteine-TBTP (4-thiobutyltriphenylphosphonium) synthon to investigate the delivery of non-permeable PNA (peptide nucleic acids)-based compounds to cells

  摘要：

  This paper reports: (i) the facile synthesis of a cysteine synthon incorporating both a fluorescent group and a triphenylphosphonium derivative (TBTP) via the formation of a disulphide bond, which can subsequently undergo facile intracellular scission, (ii) the direct conjugation of this synthon to a non-permeable drug, (a cyclic PNA (peptide nucleic acid)-based compound has been chosen as a model), and (iii) that this conjugation enables the efficient homogenous delivery of the otherwise non-permeable cyclic PNA into the cytoplasm of cells, as demonstrated by fluorescence microscopy. Our results indicate that this fluorescent-labelled cysteine-TBTP synthon can provide a very useful tool for exploring the cellular uptake of a large range of molecules of biological interest, containing only a single reactive function. The preparation of an activated TBTP derivative is also described and this procedure could be widely used to introduce a TBTP cation to any thio-containing molecule. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2007.01.002
• 作为产物：
  描述：

  6-O-(carboxymethyl)fluorescein ethyl ester 、 L-cystine tert-butyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以78%的产率得到N,N'-bis(6-O-(carboxymethyl)fluorescein ethyl ester)-L-cystine bis-t-butyl ester
  参考文献：
  名称：

  A “Ready-To-Use” fluorescent-labelled-cysteine-TBTP (4-thiobutyltriphenylphosphonium) synthon to investigate the delivery of non-permeable PNA (peptide nucleic acids)-based compounds to cells

  摘要：

  This paper reports: (i) the facile synthesis of a cysteine synthon incorporating both a fluorescent group and a triphenylphosphonium derivative (TBTP) via the formation of a disulphide bond, which can subsequently undergo facile intracellular scission, (ii) the direct conjugation of this synthon to a non-permeable drug, (a cyclic PNA (peptide nucleic acid)-based compound has been chosen as a model), and (iii) that this conjugation enables the efficient homogenous delivery of the otherwise non-permeable cyclic PNA into the cytoplasm of cells, as demonstrated by fluorescence microscopy. Our results indicate that this fluorescent-labelled cysteine-TBTP synthon can provide a very useful tool for exploring the cellular uptake of a large range of molecules of biological interest, containing only a single reactive function. The preparation of an activated TBTP derivative is also described and this procedure could be widely used to introduce a TBTP cation to any thio-containing molecule. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2007.01.002