2-(2-nitroimidazo-1-yl)ethanamine-DOTA | 1300727-13-2

• 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: 2-(2-nitroimidazo-1-yl)ethanamine-DOTA
• 英文别名: 2-[4,7-Bis(carboxymethyl)-10-[2-[2-(2-nitroimidazol-1-yl)ethylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 1300727-13-2
• 化学式: C₂₁H₃₄N₈O₉
• 分子量: 542.549
• InChiKey: FFRGXRHWQLVNHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  218
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸 、 2-(2-硝基-1H-咪唑-1-基)乙胺盐酸盐 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以53.7%的产率得到2-(2-nitroimidazo-1-yl)ethanamine-DOTA
  参考文献：
  名称：

  Synthesis of 68Ga-labeled DOTA-nitroimidazole derivatives and their feasibilities as hypoxia imaging PET tracers

  摘要：

  The imaging of hypoxia is important for therapeutic decision making in various diseases. Ga-68 is an important radionuclide for positron emission tomography (PET), and its usage is increasing, due to the development of the Ge-68/Ga-68-generator. In the present study, the authors synthesized two nitroimidazole derivatives by conjugating nitroimidazole and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) via an amide bond (4) and a thiourea bond (5). Both derivatives were labeled with Ga-68 with high labeling efficiency and were stable after labeling. The low partition coefficients (log P) of Ga-68-4 (-4.6) and Ga-68-5 (-4.5) demonstrated the hydrophilic natures of the derivatives, and both showed higher uptake in cancer cell lines cultured under hypoxic condition than under normoxic condition. However, Ga-68-5 showed higher liver uptake than Ga-68-4 in a biodistribution study due to higher lipophilicity. In an animal PET study, Ga-68-4 showed higher standard uptake values (SUV) in tumors than Ga-68-5 in mice xenografted with CT-26 mouse colon cancer cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.041