[11C]-m-hydroxy-phenethylguanidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [11C]-m-hydroxy-phenethylguanidine
• 英文别名: (11)C-meta-hydroxyphenethylguanidine；2-[2-(3-Hydroxyphenyl)ethyl]guanidine
• 化学式: C₉H₁₃N₃O
• mdl: MFCD20547474
• 分子量: 179.222
• InChiKey: OZGANZKCVKSMQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-羟基苯乙胺盐酸盐 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 5.0h， 生成 [11C]-m-hydroxy-phenethylguanidine
  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

• Imaging agents
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US10259781B2

  公开（公告）日：2019-04-16

  Provided herein is technology relating to imaging agents and particularly, but not exclusively, to methods of manufacturing fluorine-18-labeled phenethylguanidines and uses thereof.

  本文提供的是与成像剂有关的技术，特别是（但不限于）制造氟-18 标记的苯乙胍及其用途的方法。
• IMAGING AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20150246142A1

  公开（公告）日：2015-09-03

  Provided herein is technology relating to imaging agents and particularly, but not exclusively, to methods of manufacturing fluorine-18-labeled phenethylguanidines and uses thereof.
• US7534418B2
  申请人：——

  公开号：US7534418B2

  公开（公告）日：2009-05-19
• 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.