4-<18F>fluoro-m-tyramine

• 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: 4-<18F>fluoro-m-tyramine
• 英文别名: 4-[¹⁸F]fluoro-m-tyramine；[¹⁸F]4F-MTA；5-(2-aminoethyl)-2-(18F)fluoranylphenol
• 化学式: C₈H₁₀FNO
• 分子量: 154.173
• InChiKey: BQDIGRQKBKSZPE-RVRFMXCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴化氰 、 4-<18F>fluoro-m-tyramine 在 ammonium hydroxide 、 溴化铵 作用下， 以 乙腈 为溶剂， 反应 0.3h， 生成 (4-[¹⁸F]fluoro-m-hydroxyphenethyl)guanidine
  参考文献：
  名称：

  Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation

  摘要：

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.106
• 作为产物：
  描述：

  3-benzyloxy-4-N,N-dimethylaminobenzaldehyde 在 lithium aluminium tetrahydride 、 Kryptofix [2.2.2] 、 ammonium acetate 、 溶剂黄146 、 diborane(6) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-<18F>fluoro-m-tyramine
  参考文献：
  名称：

  Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation

  摘要：

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.106

文献信息

• Synthesis of 6-[18F]fluorodopamine, 6-[18F]fluoro-m-tyramine and 4-[18F]fluoro-m-tyramine+
  作者：Mohammad Namavari、N. Satyamurthy、Jorge R. Barrio

  DOI：10.1002/jlcr.2580360903

  日期：1995.9

  A new method for the preparation of 6-[18F]fluorodopamine (3) and [18F]fluorinated analogs of m-tyramine based on a regioselective radiofluorodestannylation reaction has been developed. The radiofluorodestannylation of 6-trimethylstannyldopamine derivative 1 was carried out with [18F]F2 to give the corresponding [18F]fluoro intermediate 2. Acid deprotection of 2 with 48% HBr followed by HPLC purification afforded 6-[18F]fluorodopamine (3) in 18% radiochemical yield. Similarly, 6- and 4-[18F]fluoro-m-tyramines (6a and 6b) were prepared from their corresponding trimethylstannyl-m-tyramine derivatives in 25 and 8% radiochemical yields, respectively. In all cases, after HPLC purification of the final products, tin concentrations were found to be <15 ppb.

  基于位点选择性放射性氟化脱锡反应，我们开发了一种制备6-[18F]氟多巴胺（3）和[18F]氟代间酪胺类似物的新方法。用[18F]F2对6-三甲基锡代多巴胺衍生物1进行放射性氟化脱锡反应，得到相应的[18F]氟中间体2。用48%的HBr对2进行酸脱保护，然后进行HPLC纯化，得到6-[18F]氟多巴胺（3），放射化学收率为18%。同样，6-和4-[18F]氟-间酪胺（6a和6b）分别由其相应的三甲基锡代-间酪胺衍生物制备，放射化学收率分别为25%和8%。在所有情况下，对最终产物进行HPLC纯化后，锡浓度均小于15ppb。
• Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation
  作者：Keun Sam Jang、Yong-Woon Jung、Phillip S. Sherman、Carole A. Quesada、Guie Gu、David M. Raffel

  DOI：10.1016/j.bmcl.2013.01.106

  日期：2013.3

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.