[11C]epinephrine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [11C]epinephrine
• 英文别名: [11C]-Epinephrine；4-[(1R)-1-hydroxy-2-((111C)methylamino)ethyl]benzene-1,2-diol
• 化学式: C₉H₁₃NO₃
• 分子量: 182.196
• InChiKey: UCTWMZQNUQWSLP-UTDSSMFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  去甲肾上腺素 、 [11C]methyl triflate 以 二甲基亚砜 为溶剂， 生成 [11C]epinephrine
  参考文献：
  名称：

  Radiolabeled Phenethylguanidines:  Novel Imaging Agents for Cardiac Sympathetic Neurons and Adrenergic Tumors

  摘要：

  The norepinephrine transporter (NET) substrates [I-123]-m-iodobenzylguanidine (MIBG) and [C-11]-m-hydroxyephedrine (HED) are used as markers of cardiac sympathetic neurons and adrenergic tumors (pheochromocytoma, neuroblastoma). However, their rapid NET transport rates limit their ability to provide accurate measurements of cardiac nerve density. [C-11]Phenethylguanidine ([C-11]1a) and 12 analogues ([C-11]1b-m) were synthesized and evaluated as radiotracers with improved kinetics for quantifying cardiac nerve density. In isolated rat hearts, neuronal uptake rates of [C-11]1a-m ranged from 0.24 to 1.96 mL min(-1) (g wet wt)(-1), and six compounds had extremely long neuronal retention times (clearance T-1/2 > 20 h) due to efficient vesicular storage. Positron emission tomography (PET) studies in nonhuman primates with [C-11]1e, N-[C-11]guanyl-m-octopamine, which has a slow NET transport rate, showed improved myocardial kinetics compared to HED. Compound [C-11]1c, [C-11]-p-hydroxyphenethylguanidine, which has a rapid NET transport rate, avidly accumulated into rat pheochromocytoma xenograft tumors in mice. These encouraging findings demonstrate that radiolabeled phenethylguanidines deserve further investigation as radiotracers of cardiac sympathetic innervation and adrenergic tumors.

  DOI：

  10.1021/jm061398y

文献信息

• STEINBACH, J.;BEYER, G. -J.;GUNTHER, K., ZENTRALINST. KERNFORSCH. ROSSENDORF DRESDEN. <BER.>,(1989) N69, C. 29
  作者：STEINBACH, J.、BEYER, G. -J.、GUNTHER, K.

  DOI：——

  日期：——
• Radiolabeled Phenethylguanidines:  Novel Imaging Agents for Cardiac Sympathetic Neurons and Adrenergic Tumors
  作者：David M. Raffel、Yong-Woon Jung、David L. Gildersleeve、Phillip S. Sherman、James J. Moskwa、Louis J. Tluczek、Wei Chen

  DOI：10.1021/jm061398y

  日期：2007.5.1

  The norepinephrine transporter (NET) substrates [I-123]-m-iodobenzylguanidine (MIBG) and [C-11]-m-hydroxyephedrine (HED) are used as markers of cardiac sympathetic neurons and adrenergic tumors (pheochromocytoma, neuroblastoma). However, their rapid NET transport rates limit their ability to provide accurate measurements of cardiac nerve density. [C-11]Phenethylguanidine ([C-11]1a) and 12 analogues ([C-11]1b-m) were synthesized and evaluated as radiotracers with improved kinetics for quantifying cardiac nerve density. In isolated rat hearts, neuronal uptake rates of [C-11]1a-m ranged from 0.24 to 1.96 mL min(-1) (g wet wt)(-1), and six compounds had extremely long neuronal retention times (clearance T-1/2 > 20 h) due to efficient vesicular storage. Positron emission tomography (PET) studies in nonhuman primates with [C-11]1e, N-[C-11]guanyl-m-octopamine, which has a slow NET transport rate, showed improved myocardial kinetics compared to HED. Compound [C-11]1c, [C-11]-p-hydroxyphenethylguanidine, which has a rapid NET transport rate, avidly accumulated into rat pheochromocytoma xenograft tumors in mice. These encouraging findings demonstrate that radiolabeled phenethylguanidines deserve further investigation as radiotracers of cardiac sympathetic innervation and adrenergic tumors.