SCN-NOTA-2-NI-N-ethylamine | 1242543-24-3

• 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: SCN-NOTA-2-NI-N-ethylamine
• 英文别名: 2-[4,7-Bis(carboxymethyl)-5-[[4-[2-(2-nitroimidazol-1-yl)ethylcarbamothioylamino]phenyl]methyl]-1,4,7-triazonan-1-yl]acetic acid
• CAS: 1242543-24-3
• 化学式: C₂₅H₃₄N₈O₈S
• 分子量: 606.66
• InChiKey: RCQBLVRIXDBIPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  241
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  SCN-NOTA 、 2-(2-硝基-1H-咪唑-1-基)乙胺盐酸盐 在 三乙胺 作用下， 以 氯仿 为溶剂， 以73%的产率得到SCN-NOTA-2-NI-N-ethylamine
  参考文献：
  名称：

  Synthesis and Characterization of Nitroimidazole Derivatives for ⁶⁸Ga-Labeling and Testing in Tumor Xenografted Mice

  摘要：

  Radiolabeled nitroimidazole (NI) derivatives have been used for imaging hypoxic tissues. We synthesized NI derivatives conjugated with bifunctional chelating agents such as 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA) and isothiocyanatobenzyl-NOTA (SCN-NOTA) via ethyleneamine bridge by formation of amide and thiourea bond, respectively. We proved that amide oxygen of Ga-NOTA-NI contributes to the formation of metal complex by X-ray crystallography. We labeled them with Ga-68 and found that both Ga-68-NOTA-NI and Ga-68- SCN-NOTA-NI were labeled in high efficiency (> 96%) and were stable at room temperature in the prepared medium and at 37 degrees C in human serum. In vitro cell uptake experiments using CHO and CT-26 cell lines showed significantly increased uptakes of both of the agents in hypoxic condition. Biodistribution study in CT-26 xenografted mice showed increasing tumor to muscle ratios. Ga-68-NOTA-NI showed lower intestine uptake than Ga-68-NOTA-SCN-NI due to hydrophilicity. Also, Ga-68-NOTA-NI showed higher tumor uptake than Ga-68-NOTA-SCN-NI in an animal PET study. In conclusion, we successfully developed Ga-68 labeled NI derivatives for hypoxic tissue imaging.

  DOI：

  10.1021/jm100545a

文献信息

• Synthesis and Characterization of Nitroimidazole Derivatives for ⁶⁸Ga-Labeling and Testing in Tumor Xenografted Mice
  作者：Lathika Hoigebazar、Jae Min Jeong、Soo Young Choi、Jae Yeon Choi、Dinesh Shetty、Yun-Sang Lee、Dong Soo Lee、June-Key Chung、Myung Chul Lee、Young Keun Chung

  DOI：10.1021/jm100545a

  日期：2010.9.9

  Radiolabeled nitroimidazole (NI) derivatives have been used for imaging hypoxic tissues. We synthesized NI derivatives conjugated with bifunctional chelating agents such as 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA) and isothiocyanatobenzyl-NOTA (SCN-NOTA) via ethyleneamine bridge by formation of amide and thiourea bond, respectively. We proved that amide oxygen of Ga-NOTA-NI contributes to the formation of metal complex by X-ray crystallography. We labeled them with Ga-68 and found that both Ga-68-NOTA-NI and Ga-68- SCN-NOTA-NI were labeled in high efficiency (> 96%) and were stable at room temperature in the prepared medium and at 37 degrees C in human serum. In vitro cell uptake experiments using CHO and CT-26 cell lines showed significantly increased uptakes of both of the agents in hypoxic condition. Biodistribution study in CT-26 xenografted mice showed increasing tumor to muscle ratios. Ga-68-NOTA-NI showed lower intestine uptake than Ga-68-NOTA-SCN-NI due to hydrophilicity. Also, Ga-68-NOTA-NI showed higher tumor uptake than Ga-68-NOTA-SCN-NI in an animal PET study. In conclusion, we successfully developed Ga-68 labeled NI derivatives for hypoxic tissue imaging.