2,2'-(7-(2-oxo-2-((2-(11-(tritylthio)undecanamido)ethyl)amino)ethyl)-1,4,7-triazonane-1,4-diyl)diacetic acid | 1513787-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,2'-(7-(2-oxo-2-((2-(11-(tritylthio)undecanamido)ethyl)amino)ethyl)-1,4,7-triazonane-1,4-diyl)diacetic acid
• CAS: 1513787-39-7
• 化学式: C₅₂H₇₇N₅O₆S
• 分子量: 900.279
• InChiKey: PSHAVWOYCKUWIL-UHFFFAOYSA-N

物化性质

• 沸点：
  938.9±65.0 °C(predicted)
• 密度：
  1.085±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  64.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  120.52
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,2'-(7-(2-oxo-2-((2-(11-(tritylthio)undecanamido)ethyl)amino)ethyl)-1,4,7-triazonane-1,4-diyl)diacetic acid 在 三氟乙酸 作用下， 以 乙硫醇 为溶剂， 反应 96.0h， 以52%的产率得到2,2'-(7-(2-((2-(11-mercaptoundecanamido)ethyl)amino)-2-oxoethyl)-1,4,7-triazonane-1,4-diyl)diacetic acid
  参考文献：
  名称：

  ⁶⁸Ga-Labeled Gold Glyconanoparticles for Exploring Blood–Brain Barrier Permeability: Preparation, Biodistribution Studies, and Improved Brain Uptake via Neuropeptide Conjugation

  摘要：

  New tools and techniques to improve brain visualization and assess drug permeability across the blood brain barrier (BBB) are critically needed. Positron emission tomography (PET) is a highly sensitive, noninvasive technique that allows the evaluation of the BBB permeability under normal and disease-state conditions. In this work, we have developed the synthesis of novel water-soluble and biocompatible glucose-coated gold nanoparticles (GNPs) carrying BBB-permeable neuropeptides and a chelator of the positron emitter Ga-68 as a PET reporter for in vivo tracking biodistribution. The small GNPs (2 nm) are stabilized and solubilized by a glucose conjugate. A NOTA ligand is the chelating agent for the Ga-68, and two related opioid peptides are used as targeting ligands for improving BBB crossing. The radioactive labeling of the GNPs is completed in 30 min at 70 degrees C followed by purification via centrifugal filtration. As a proof of principle, a biodistribution study in rats is performed for the different Ga-68-GNPs. The accumulation of radioactivity in different organs after intravenous administration is measured by whole body PET imaging and gamma counter measurements of selected organs. The biodistribution of the Ga-68-GNPs varies depending on the ligands, as GNPs with the same gold core size show different distribution profiles. One of the targeted Ga-68-GNPs improves BBB crossing near 3-fold (0.020 +/- 0.0050% ID/g) compared to nontargeted GNPs (0.0073 +/- 0.0024% ID/g) as measured by dissection and tissue counting.

  DOI：

  10.1021/ja411096m
• 作为产物：
  描述：

  11-(tritylthio)undecanoic acid 、 di-tert-butyl 2,2'-(7-(2-((2-aminoethyl)amino)-2-oxoethyl)-1,4,7-triazonane-1,4-diyl)diacetate 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium 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 20.5h， 以54%的产率得到2,2'-(7-(2-oxo-2-((2-(11-(tritylthio)undecanamido)ethyl)amino)ethyl)-1,4,7-triazonane-1,4-diyl)diacetic acid
  参考文献：
  名称：

  ⁶⁸Ga-Labeled Gold Glyconanoparticles for Exploring Blood–Brain Barrier Permeability: Preparation, Biodistribution Studies, and Improved Brain Uptake via Neuropeptide Conjugation

  摘要：

  New tools and techniques to improve brain visualization and assess drug permeability across the blood brain barrier (BBB) are critically needed. Positron emission tomography (PET) is a highly sensitive, noninvasive technique that allows the evaluation of the BBB permeability under normal and disease-state conditions. In this work, we have developed the synthesis of novel water-soluble and biocompatible glucose-coated gold nanoparticles (GNPs) carrying BBB-permeable neuropeptides and a chelator of the positron emitter Ga-68 as a PET reporter for in vivo tracking biodistribution. The small GNPs (2 nm) are stabilized and solubilized by a glucose conjugate. A NOTA ligand is the chelating agent for the Ga-68, and two related opioid peptides are used as targeting ligands for improving BBB crossing. The radioactive labeling of the GNPs is completed in 30 min at 70 degrees C followed by purification via centrifugal filtration. As a proof of principle, a biodistribution study in rats is performed for the different Ga-68-GNPs. The accumulation of radioactivity in different organs after intravenous administration is measured by whole body PET imaging and gamma counter measurements of selected organs. The biodistribution of the Ga-68-GNPs varies depending on the ligands, as GNPs with the same gold core size show different distribution profiles. One of the targeted Ga-68-GNPs improves BBB crossing near 3-fold (0.020 +/- 0.0050% ID/g) compared to nontargeted GNPs (0.0073 +/- 0.0024% ID/g) as measured by dissection and tissue counting.

  DOI：

  10.1021/ja411096m