5-bromo-2,2'-bithiophene-5'-succinimidyl ester | 876754-66-4

• 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-bromo-2,2'-bithiophene-5'-succinimidyl ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 5-(5-bromothiophen-2-yl)thiophene-2-carboxylate
• CAS: 876754-66-4
• 化学式: C₁₃H₈BrNO₄S₂
• 分子量: 386.247
• InChiKey: OIDFHGHTYYIIHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(1-哌啶基)苯硼酸频哪酯 、 5-bromo-2,2'-bithiophene-5'-succinimidyl ester 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以70%的产率得到2,5-dioxopyrrolidin-1-yl 5'-(4-(piperidin-1-yl)phenyl)-2,2'-bithiophene-5-carboxylate
  参考文献：
  名称：

  Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

  摘要：

  开发了一系列结构相关的细胞渗透性噻吩荧光团，其特征是活体小鼠胚胎成纤维细胞内强烈的绿色或红色荧光。荧光团表现出快速内化、细胞内出色的保留以及胞质环境中的高光学稳定性，并且不会改变细胞活力和重现性。根据分子结构，它们在细胞内经历了不同的命运：从细胞质的明亮而持久的染色到一小组球状蛋白的选择性标记。

  DOI：

  10.1039/c3ob41982g
• 作为产物：
  描述：

  (2,5-Dioxopyrrolidin-1-yl) 5-thiophen-2-ylthiophene-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 生成 5-bromo-2,2'-bithiophene-5'-succinimidyl ester
  参考文献：
  名称：

  推挽式氨基琥珀酰亚胺基噻吩基荧光染料：合成和光学表征

  摘要：

  介绍了新型荧光染料的设计和合成，该染料的发射范围为490–650 nm。它们的结构和电子特性已通过实验技术和量子化学计算进行了表征。发色团是具有苯基和噻吩环的π桥的供体-π-桥-受体推挽化合物及其组合。与以前的噻吩荧光团相比，这些染料在吸收和发射光谱中显示出明显的红移，并提供紧凑的红色发光荧光团。该染料具有氨基琥珀酰亚胺基活性酯，可以很容易地与蛋白质，聚合物和其他含氨基的物质结合。

  DOI：

  10.1002/chem.201100142

文献信息

• Oligonucleotide Probes
  申请人：Barbarella Giovanna

  公开号：US20090137789A1

  公开（公告）日：2009-05-28

  Fluorescent oligonucleotide probe having a general formula (I), wherein Onu represents an oligonucleotide residue, Thio n represents a fluorescent oligothiophene containing n thiophenic rings, n being an integer lower than 8, L representing a binder conceived to maintain Thio n mobile in relation to Onu in a manner so that Thio n can perform its fluorescent action correctly, and Onu can perform its hybridization action. (I)=Onu-L-Thio n .

  具有一般式（I）的荧光寡核苷酸探针，其中Onu代表寡核苷酸残基，Thion代表含有n个噻吩环的荧光寡噻吩，n为小于8的整数，L代表绑定剂，旨在以一种使Thion能够正确发挥其荧光作用的方式将Thion与Onu相关联，而Onu可以发挥其杂交作用。（I）= Onu-L-Thion。
• Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils
  作者：Ilaria Palamà、Francesca Di Maria、Ilenia Viola、Eduardo Fabiano、Giuseppe Gigli、Cristian Bettini、Giovanna Barbarella

  DOI：10.1021/ja2065522

  日期：2011.11.9

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.
• Push–Pull Amino Succinimidyl Ester Thiophene‐Based Fluorescent Dyes: Synthesis and Optical Characterization
  作者：Giovanna Sotgiu、Matteo Galeotti、Cristian Samorí、Alessandro Bongini、Andrea Mazzanti

  DOI：10.1002/chem.201100142

  日期：2011.7.4

  The design and synthesis of new fluorescent dyes with emission range at 490–650 nm are described. Their structural and electronic properties have been characterized by both experimental techniques and quantum‐chemical calculations. The chromophores are donor–π‐bridge–acceptor push–pull compounds with a π bridge of phenyl and thiophene rings and their combination. Compared with previous thiophene fluorophores

  介绍了新型荧光染料的设计和合成，该染料的发射范围为490–650 nm。它们的结构和电子特性已通过实验技术和量子化学计算进行了表征。发色团是具有苯基和噻吩环的π桥的供体-π-桥-受体推挽化合物及其组合。与以前的噻吩荧光团相比，这些染料在吸收和发射光谱中显示出明显的红移，并提供紧凑的红色发光荧光团。该染料具有氨基琥珀酰亚胺基活性酯，可以很容易地与蛋白质，聚合物和其他含氨基的物质结合。
• Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores
  作者：F. Di Maria、I. E. Palamà、M. Baroncini、A. Barbieri、A. Bongini、R. Bizzarri、G. Gigli、G. Barbarella

  DOI：10.1039/c3ob41982g

  日期：——

  A structurally correlated series of cell-permeant thiophene fluorophores, characterized by intense green or red fluorescence inside live mouse embryonic fibroblasts, was developed. The fluorophores displayed rapid internalization, excellent retention inside the cells, and high optical stability in the cytosolic environment and did not alter cell viability and reproducibility. Depending on the molecular structure, they experienced distinct fate inside the cells: from bright and lasting staining of the cytoplasm to selective tagging of a small set of globular proteins.

  开发了一系列结构相关的细胞渗透性噻吩荧光团，其特征是活体小鼠胚胎成纤维细胞内强烈的绿色或红色荧光。荧光团表现出快速内化、细胞内出色的保留以及胞质环境中的高光学稳定性，并且不会改变细胞活力和重现性。根据分子结构，它们在细胞内经历了不同的命运：从细胞质的明亮而持久的染色到一小组球状蛋白的选择性标记。