5-(2-aminoethyl)-2,2':5',2''-terthiophene | 385369-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-(2-aminoethyl)-2,2':5',2''-terthiophene
• 英文别名: 2-[5-(5-Thiophen-2-ylthiophen-2-yl)thiophen-2-yl]ethanamine
• CAS: 385369-24-4
• 化学式: C₁₄H₁₃NS₃
• 分子量: 291.462
• InChiKey: KZBPGRUIVBBOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二吡啶硫碳酸酯 、 5-(2-aminoethyl)-2,2':5',2''-terthiophene 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-(2-isothiocyanatoethyl)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Oligothiophene Isothiocyanates as a New Class of Fluorescent Markers for Biopolymers

  摘要：

  The regioselective synthesis of fluorescent oligothiophene isothiocyanates is described. The isothiocyanates were reacted with bovine serum albumin (BSA) following standard procedures and the optical properties of the oligothiophene-BSA conjugates were analyzed as a function of oligomer concentration, time, and irradiation power. The oligothiophene-BSA conjugates were chemically very stable and their photoluminescence characteristics persisted unaltered for several months. Photoluminescence data relative to the conjugate of an oligothiophene-S,S-dioxide isothiocyanate with monoclonal anti-CD8 antibody are reported. No fluorescence quenching was observed following the binding of the isothiocyanate to the antibody and the conjugate displayed high chemical stability and photostability.

  DOI：

  10.1021/ja011209v
• 作为产物：
  描述：

  5-(2-azidoethyl)-2,2':5',2''-terthiophene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 5-(2-aminoethyl)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Oligothiophene Isothiocyanates as a New Class of Fluorescent Markers for Biopolymers

  摘要：

  The regioselective synthesis of fluorescent oligothiophene isothiocyanates is described. The isothiocyanates were reacted with bovine serum albumin (BSA) following standard procedures and the optical properties of the oligothiophene-BSA conjugates were analyzed as a function of oligomer concentration, time, and irradiation power. The oligothiophene-BSA conjugates were chemically very stable and their photoluminescence characteristics persisted unaltered for several months. Photoluminescence data relative to the conjugate of an oligothiophene-S,S-dioxide isothiocyanate with monoclonal anti-CD8 antibody are reported. No fluorescence quenching was observed following the binding of the isothiocyanate to the antibody and the conjugate displayed high chemical stability and photostability.

  DOI：

  10.1021/ja011209v

文献信息

• Fluorescent labeling of human mesenchymal stem cells by thiophene fluorophores conjugated to a lipophilic carrier
  作者：Maria Duca、Barbara Dozza、Enrico Lucarelli、Spartaco Santi、Audrey Di Giorgio、Giovanna Barbarella

  DOI：10.1039/c0cc01918f

  日期：——

  Fluorescent labeling of human mesenchymal stem cells (hMSCs) is essential for their study in vitro and in vivo. Here, we report a new chemical biodelivery method for labeling hMSCs using a series of very efficient and highly versatile thiophene-based fluorescent dyes. Such conjugates contribute to a stable and viable labeling of hMSCs and constitute a promising strategy for in vivo applications.

  人类间充质干细胞（hMSCs）的荧光标记对其体外和体内研究至关重要。在此，我们报告了一种新的化学生物递送方法，利用一系列非常高效且用途广泛的噻吩基荧光染料对 hMSCs 进行标记。这种共轭物有助于对 hMSCs 进行稳定而可行的标记，是一种很有前途的体内应用策略。