N-(2-[18F]fluoroethyl)-4-piperidinol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(2-[18F]fluoroethyl)-4-piperidinol
• 英文别名: 1-(2-(18F)fluoranylethyl)piperidin-4-ol
• 化学式: C₇H₁₄FNO
• 分子量: 146.194
• InChiKey: YUPRNALANWTJTB-COJKEBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [18F]fluoroethyl-4-piperidyl acetate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.08h， 生成 N-(2-[18F]fluoroethyl)-4-piperidinol
  参考文献：
  名称：

  N-[18F]fluoroethyl-4-piperidyl acetate ([18F]FEtP4A)

  摘要：

  N-[F-18]Fluoroethyl-4-piperidyl acetate ([F-18]FEtP4A) was synthesized and evaluated as a PET tracer for imaging brain acetylcholinesterase (AchE) in vivo. [F-18]FEtP4A was previously prepared by reacting 4-piperidyl acetate (P4A) with 2-[F-18]fluoroethyl bromide ([F-18]FEtBr) at 130degreesC for 30 min in 37% radiochemical yield using an automated synthetic system. In this work, [F-18]FEtP4A was synthesized by reacting P4A with 2-[F-18]fluoroethyl iodide (([1)8F]FEtI) or 2-[F-18]fluoroethyl triflate ([F-18]FEtOTf in improved radiochemical yields, compared with [F-18]FEtBr under the corresponding condition. Ex vivo autoradiogram of rat brain and PET summation image of monkey brain after iv injection of [F-18]FEtP4A displayed a high radioactivity in the striatum, a region with the highest AchE activity in the brain. Moreover, the distribution pattern of F-18 radioactivity was consistent with that of AchE in the brain: striatum > frontal cortex > cerebellum. In the rat and monkey plasma, two radioactive metabolites were detected. However, their presence might not preclude the imaging studies for AchE in the brain, because they were too hydrophilic to pass the blood-brain barrier and to enter the brain. In the rat brain, only [F-18]fluoroethyl-4-piperidinol ([F-18]FEtP4OH) was detected at 30 min postinjection. The hydrolytic [F-18]FEtP4OH displayed a slow washout and a long retention in the monkey brain until the PET experiment (120 min). Although [F-18]FEtP4A is a potential PET tracer for imaging AchE in vivo, its lower hydrolytic rate and lower specificity for AchE than those of [C-11]MP4A may limit its usefulness for the quantitative measurement for AchE in the primate brain. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00177-9

文献信息

• N-[18F]fluoroethyl-4-piperidyl acetate ([18F]FEtP4A)
  作者：Ming-Rong Zhang、Kenji Furutsuka、Jun Maeda、Tatsuya Kikuchi、Takayo Kida、Takashi Okauchi、Toshiaki Irie、Kazutoshi Suzuki

  DOI：10.1016/s0968-0896(03)00177-9

  日期：2003.6

  N-[F-18]Fluoroethyl-4-piperidyl acetate ([F-18]FEtP4A) was synthesized and evaluated as a PET tracer for imaging brain acetylcholinesterase (AchE) in vivo. [F-18]FEtP4A was previously prepared by reacting 4-piperidyl acetate (P4A) with 2-[F-18]fluoroethyl bromide ([F-18]FEtBr) at 130degreesC for 30 min in 37% radiochemical yield using an automated synthetic system. In this work, [F-18]FEtP4A was synthesized by reacting P4A with 2-[F-18]fluoroethyl iodide (([1)8F]FEtI) or 2-[F-18]fluoroethyl triflate ([F-18]FEtOTf in improved radiochemical yields, compared with [F-18]FEtBr under the corresponding condition. Ex vivo autoradiogram of rat brain and PET summation image of monkey brain after iv injection of [F-18]FEtP4A displayed a high radioactivity in the striatum, a region with the highest AchE activity in the brain. Moreover, the distribution pattern of F-18 radioactivity was consistent with that of AchE in the brain: striatum > frontal cortex > cerebellum. In the rat and monkey plasma, two radioactive metabolites were detected. However, their presence might not preclude the imaging studies for AchE in the brain, because they were too hydrophilic to pass the blood-brain barrier and to enter the brain. In the rat brain, only [F-18]fluoroethyl-4-piperidinol ([F-18]FEtP4OH) was detected at 30 min postinjection. The hydrolytic [F-18]FEtP4OH displayed a slow washout and a long retention in the monkey brain until the PET experiment (120 min). Although [F-18]FEtP4A is a potential PET tracer for imaging AchE in vivo, its lower hydrolytic rate and lower specificity for AchE than those of [C-11]MP4A may limit its usefulness for the quantitative measurement for AchE in the primate brain. (C) 2003 Elsevier Science Ltd. All rights reserved.