3,6,9,12-tetraoxatetradecanoic acid 14-[[tetrahydro-2H-pyran-2-yl]oxy]phenylmethyl ester | 1318760-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6,9,12-tetraoxatetradecanoic acid 14-[[tetrahydro-2H-pyran-2-yl]oxy]phenylmethyl ester
• 英文别名: 3,6,9,12-Tetraoxatetradecanoic acid, 14-[(tetrahydro-2H-pyran-2-yl)oxy]-, phenylmethyl ester；benzyl 2-[2-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethoxy]ethoxy]acetate
• CAS: 1318760-40-5
• 化学式: C₂₂H₃₄O₈
• 分子量: 426.507
• InChiKey: RLISXXSRWCYCKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  30.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,6,9,12-tetraoxatetradecanoic acid 14-[[tetrahydro-2H-pyran-2-yl]oxy]phenylmethyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以83%的产率得到1-Benzyl 3,6,9,12,15-pentaoxadecanoate ester
  参考文献：
  名称：

  Cell uptake of a biosensor detected by hyperpolarized 129Xe NMR: The transferrin case

  摘要：

  For detection of biological events in vitro, sensors using hyperpolarized Xe-129 NMR can become a powerful tool, provided the approach can bridge the gap in sensitivity. Here we propose constructs based on the non-selective grafting of cryptophane precursors on holo-transferrin. This biological system was chosen because there are many receptors on the cell surface, and endocytosis further increases this density. The study of these biosensors with K562 cell suspensions via fluorescence microscopy and Xe-129 NMR indicates a strong interaction, as well as interesting features such as the capacity of xenon to enter the cryptophane even when the biosensor is endocytosed, while keeping a high level of polarization. Despite a lack of specificity for transferrin receptors, undoubtedly due to the hydrophobic character of the cryptophane moiety that attracts the biosensor into the cell membrane, these biosensors allow the first in-cell probing of biological events using hyperpolarized xenon. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.002
• 作为产物：
  描述：

  溴甲苯 、 四氢吡喃醚-四聚乙二醇 、 溴乙酸 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 33.0h， 以75%的产率得到3,6,9,12-tetraoxatetradecanoic acid 14-[[tetrahydro-2H-pyran-2-yl]oxy]phenylmethyl ester
  参考文献：
  名称：

  Cell uptake of a biosensor detected by hyperpolarized 129Xe NMR: The transferrin case

  摘要：

  For detection of biological events in vitro, sensors using hyperpolarized Xe-129 NMR can become a powerful tool, provided the approach can bridge the gap in sensitivity. Here we propose constructs based on the non-selective grafting of cryptophane precursors on holo-transferrin. This biological system was chosen because there are many receptors on the cell surface, and endocytosis further increases this density. The study of these biosensors with K562 cell suspensions via fluorescence microscopy and Xe-129 NMR indicates a strong interaction, as well as interesting features such as the capacity of xenon to enter the cryptophane even when the biosensor is endocytosed, while keeping a high level of polarization. Despite a lack of specificity for transferrin receptors, undoubtedly due to the hydrophobic character of the cryptophane moiety that attracts the biosensor into the cell membrane, these biosensors allow the first in-cell probing of biological events using hyperpolarized xenon. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.002