bis(pentafluorophenyl)azobis(4-cyanovalerate)

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis(pentafluorophenyl)azobis(4-cyanovalerate)
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 4-cyano-4-[[2-cyano-5-oxo-5-(2,3,4,5,6-pentafluorophenoxy)pentan-2-yl]diazenyl]pentanoate；(2,3,4,5,6-pentafluorophenyl) 4-cyano-4-[[2-cyano-5-oxo-5-(2,3,4,5,6-pentafluorophenoxy)pentan-2-yl]diazenyl]pentanoate
• 化学式: C₂₄H₁₄F₁₀N₄O₄
• 分子量: 612.384
• InChiKey: UCEWSUMUFCOEMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  bis(pentafluorophenyl)azobis(4-cyanovalerate) 、 双(硫代苯甲酰基)二硫化物 以 乙酸乙酯 为溶剂， 反应 16.0h， 以63%的产率得到pentafluorophenyl (4-phenylthiocarbonylthio-4-cyanovalerate)
  参考文献：
  名称：

  Biotinylated Polyacrylamide-Based Metal-Chelating Polymers and Their Influence on Antigen Recognition Following Conjugation to a Trastuzumab Fab Fragment

  摘要：

  We report the synthesis and characterization of metal-chelating polymers (MCPs) with a terminal biotin and a polyacrylamide backbone harboring multiple diethylenetriaminepentaacetic acid (DTPA) chelating sites. These polymers are conjugated to a streptavidin (SAv)-modified Fab fragment of trastuzumab (tmFab) and subsequently complexed with In-111 through DTPA. Trastuzumab has specific targeting ability toward human epidermal growth factor receptor-2 (HER2), which is overexpressed on some types of breast cancer cells and ovarian cancer cells. In-111 can generate Auger electrons which cause lethal DNA double strand breaks. The radioimmunoconjugates (RICs) were designed to target HER2 overexpressing cancer cells and carry multiple copies of In-111 to these cells. The mole maximum specific activities of these polymers were investigated by loading the polymers with In-111 at an increasing In-111 to polymer ratio. The polymers show 55-fold to 138-fold higher maximum specific activity than DTPA modified tmFab-SAv. Moreover, the HER2 immunoreactivities of these RICs were evaluated by measuring their specific binding ability toward HER2 overexpressing SKOV-3 ovarian cancer cells. The results demonstrate that although in the presence of polymer there is increased nonspecific binding, HER2 targeting ability was retained, ensuring the radionuclide delivery ability of these RICs.

  DOI：

  10.1021/bm300843u
• 作为产物：
  描述：

  三氟乙酸五氟苯酯 、 4,4'-偶氮双(4-氰基戊酸) 以 二氯甲烷 为溶剂， 反应 6.0h， 以25%的产率得到bis(pentafluorophenyl)azobis(4-cyanovalerate)
  参考文献：
  名称：

  模型细胞表面的分层组装：粘蛋白模拟聚合物的合成及其在支撑双层上的显示

  摘要：

  细胞表面现象的分子水平分析可以受益于包含结构定义组件的模型系统。在这里，我们展示了模型细胞表面自下而上组装的第一步 - 粘蛋白模拟物的合成及其与人工膜的结合。天然粘蛋白是密集糖基化的 O 联糖蛋白，在细胞表面具有多种功能。它们的大尺寸和广泛的糖基化使得这些生物聚合物的合成不切实际。我们设计了合成易处理的糖基化聚合物，其具有类似于天然粘蛋白的棒状扩展构象。糖基化聚合物被脂质基团末端官能化并嵌入支持的脂质双层中，在那里它们以结构依赖的方式与蛋白质受体相互作用。此外，它们在合成膜中的动态行为反映了天然生物分子的动态行为。该系统提供了一个独特的框架，用于在受控的细胞表面模拟环境中研究粘蛋白样大分子的行为。

  DOI：

  10.1021/ja067819i

文献信息

• Hierarchical Assembly of Model Cell Surfaces:  Synthesis of Mucin Mimetic Polymers and Their Display on Supported Bilayers
  作者：David Rabuka、Raghuveer Parthasarathy、Goo Soo Lee、Xing Chen、Jay T. Groves、Carolyn R. Bertozzi

  DOI：10.1021/ja067819i

  日期：2007.5.1

  impractical. We designed synthetically tractable glycosylated polymers that possess rodlike extended conformations similar to natural mucins. The glycosylated polymers were end-functionalized with lipid groups and embedded into supported lipid bilayers where they interact with protein receptors in a structure-dependent manner. Furthermore, their dynamic behavior in synthetic membranes mirrored that of natural

  细胞表面现象的分子水平分析可以受益于包含结构定义组件的模型系统。在这里，我们展示了模型细胞表面自下而上组装的第一步 - 粘蛋白模拟物的合成及其与人工膜的结合。天然粘蛋白是密集糖基化的 O 联糖蛋白，在细胞表面具有多种功能。它们的大尺寸和广泛的糖基化使得这些生物聚合物的合成不切实际。我们设计了合成易处理的糖基化聚合物，其具有类似于天然粘蛋白的棒状扩展构象。糖基化聚合物被脂质基团末端官能化并嵌入支持的脂质双层中，在那里它们以结构依赖的方式与蛋白质受体相互作用。此外，它们在合成膜中的动态行为反映了天然生物分子的动态行为。该系统提供了一个独特的框架，用于在受控的细胞表面模拟环境中研究粘蛋白样大分子的行为。
• Biotinylated Polyacrylamide-Based Metal-Chelating Polymers and Their Influence on Antigen Recognition Following Conjugation to a Trastuzumab Fab Fragment
  作者：Peng Liu、Amanda J. Boyle、Yijie Lu、Raymond M. Reilly、Mitchell A. Winnik

  DOI：10.1021/bm300843u

  日期：2012.9.10

  We report the synthesis and characterization of metal-chelating polymers (MCPs) with a terminal biotin and a polyacrylamide backbone harboring multiple diethylenetriaminepentaacetic acid (DTPA) chelating sites. These polymers are conjugated to a streptavidin (SAv)-modified Fab fragment of trastuzumab (tmFab) and subsequently complexed with In-111 through DTPA. Trastuzumab has specific targeting ability toward human epidermal growth factor receptor-2 (HER2), which is overexpressed on some types of breast cancer cells and ovarian cancer cells. In-111 can generate Auger electrons which cause lethal DNA double strand breaks. The radioimmunoconjugates (RICs) were designed to target HER2 overexpressing cancer cells and carry multiple copies of In-111 to these cells. The mole maximum specific activities of these polymers were investigated by loading the polymers with In-111 at an increasing In-111 to polymer ratio. The polymers show 55-fold to 138-fold higher maximum specific activity than DTPA modified tmFab-SAv. Moreover, the HER2 immunoreactivities of these RICs were evaluated by measuring their specific binding ability toward HER2 overexpressing SKOV-3 ovarian cancer cells. The results demonstrate that although in the presence of polymer there is increased nonspecific binding, HER2 targeting ability was retained, ensuring the radionuclide delivery ability of these RICs.