(S,S,S)-2-(2-carboxycyclopropyl)-2-(3-[(11)C]methoxyphenethyl)glycine dimethyl ester | 1364738-92-0

• 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: (S,S,S)-2-(2-carboxycyclopropyl)-2-(3-[(11)C]methoxyphenethyl)glycine dimethyl ester
• 英文别名: methyl (1S,2S)-2-[(2S)-2-amino-1-methoxy-4-(3-(111C)methoxyphenyl)-1-oxobutan-2-yl]cyclopropane-1-carboxylate
• CAS: 1364738-92-0
• 化学式: C₁₇H₂₃NO₅
• 分子量: 320.362
• InChiKey: QIRMFCODGRJNBR-PVRMTJJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (1S,2S)-2-((S)-2-((tert-butoxycarbonyl)amino)-1-methoxy-4-(3-(methoxy-11C)phenyl)-1-oxobutan-2-yl)cyclopropane-1-carboxylate 在 三氟乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.2h， 生成 (S,S,S)-2-(2-carboxycyclopropyl)-2-(3-[(11)C]methoxyphenethyl)glycine dimethyl ester
  参考文献：
  名称：

  Radiosynthesis of PET radiotracer as a prodrug for imaging group II metabotropic glutamate receptors in vivo

  摘要：

  Group II metabotropic glutamate receptors (mGluRs) have been implicated in a variety of neurological and psychiatric disorders in recent studies. As a noninvasive medical imaging technique and a powerful tool in neurological research, positron emission tomography (PET) offers the possibility to visualize and study group II mGluRs in vivo under physiologic and pathologic conditions. We synthesized a PET tracer, (S,S,S)-2-(2-carboxycyclopropyl)-2-(3-[C-11]methoxyphenethyl) glycine dimethyl ester ([C-11]CMGDE), as a prodrug for group II mGluRs, and studied its preliminary biological properties in Sprague-Dawley rats to visualize group II mGluRs. The microPET studies demonstrated that [C-11]CMGDE readily penetrated into the brain and the radiotracer generated from [C-11]CMGDE had fast reversible binding in the group II mGluRs rich regions including striatum, hippocampus and different cortical areas. Blocking studies with LY341495 showed 20-30% decrease of binding of the radiotracer generated from [C-11]CMGDE in all brain areas with the highest decrease in the striatum 31.5 +/- 3.2%. The results show [C-11]CMGDE is the first PET tracer that is brain penetrating and can be used to image group II mGluRs in vivo. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.039

文献信息

• Radiosynthesis of PET radiotracer as a prodrug for imaging group II metabotropic glutamate receptors in vivo
  作者：Ji-Quan Wang、Zhaoda Zhang、Darshini Kuruppu、Anna-Liisa Brownell

  DOI：10.1016/j.bmcl.2012.01.039

  日期：2012.3

  Group II metabotropic glutamate receptors (mGluRs) have been implicated in a variety of neurological and psychiatric disorders in recent studies. As a noninvasive medical imaging technique and a powerful tool in neurological research, positron emission tomography (PET) offers the possibility to visualize and study group II mGluRs in vivo under physiologic and pathologic conditions. We synthesized a PET tracer, (S,S,S)-2-(2-carboxycyclopropyl)-2-(3-[C-11]methoxyphenethyl) glycine dimethyl ester ([C-11]CMGDE), as a prodrug for group II mGluRs, and studied its preliminary biological properties in Sprague-Dawley rats to visualize group II mGluRs. The microPET studies demonstrated that [C-11]CMGDE readily penetrated into the brain and the radiotracer generated from [C-11]CMGDE had fast reversible binding in the group II mGluRs rich regions including striatum, hippocampus and different cortical areas. Blocking studies with LY341495 showed 20-30% decrease of binding of the radiotracer generated from [C-11]CMGDE in all brain areas with the highest decrease in the striatum 31.5 +/- 3.2%. The results show [C-11]CMGDE is the first PET tracer that is brain penetrating and can be used to image group II mGluRs in vivo. (c) 2012 Elsevier Ltd. All rights reserved.