(S)-2-amino-3-(4-((1s,3R)-3-(fluoro-18F)cyclobutoxy)phenyl)propanoic acid | 1262278-79-4

• 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)-2-amino-3-(4-((1s,3R)-3-(fluoro-18F)cyclobutoxy)phenyl)propanoic acid
• CAS: 1262278-79-4
• 化学式: C₁₃H₁₆FNO₃
• 分子量: 252.275
• InChiKey: AJZRDQFGXMMUPH-PJKDETSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  trans-3-[18F]fluorocyclobutyl toluene-4-sulfonate 、 L-酪氨酸 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以8%的产率得到(S)-2-amino-3-(4-((1s,3R)-3-(fluoro-18F)cyclobutoxy)phenyl)propanoic acid
  参考文献：
  名称：

  Investigations into the synthesis, radiofluorination and conjugation of a new [18F]fluorocyclobutyl prosthetic group and its in vitro stability using a tyrosine model system

  摘要：

  The [F-18]fluorocyclobutyl group has the potential to be a metabolically stable prosthetic group for PET tracers. The synthesis of the radiolabeling precursor cis-cyclobutane-1,3-diyl bis(toluene-4-sulfonate) 8 was obtained from epibromohydrin in 7 steps (2% overall yield). The radiolabeling of this precursor 8 and its conjugation to L-tyrosine as a model system was successfully achieved to give the new non-natural amino acid 3-[F-18]fluorocyclobutyl-L-tyrosine (L-3-[F-18]FCBT) [F-18] 17 in 8% decay-corrected yield from the non-carrier-added [F-18] fluoride. L-3-[F-18] FCBT was investigated in vitro in different cancer cell lines to determine the uptake and stability. The tracer [F-18] 17 showed a time dependent uptake into different tumor cell lines (A549, NCI-H460, DU145) with the best uptake of 5.8% injected dose per 5 x 10(5) cells after 30 min in human lung carcinoma cells A549. The stability of L-3-[F-18] FCBT in human and rat plasma and the stability of the non-radioactive L-3-FCBT in rat hepatocytes were both found to be excellent. These results show that the non-natural amino acid L-3-[F-18] FCBT is a promising metabolically stable radiotracer for positron emission tomography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.049

文献信息

• Radiolabelling Method Using Cycloalkyl Groups
  申请人：Graham Keith

  公开号：US20120189546A1

  公开（公告）日：2012-07-26

  This invention relates to novel cyclo alkyl compounds suitable for labeling by 18 F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by positron emission tomography (PET).

  本发明涉及新型环烷基化合物，适用于18F标记，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒以及这种化合物、组合物或试剂盒在正电子发射断层扫描（PET）诊断成像中的用途。
• Investigations into the synthesis, radiofluorination and conjugation of a new [18F]fluorocyclobutyl prosthetic group and its in vitro stability using a tyrosine model system
  作者：Dominic Franck、Torsten Kniess、Jörg Steinbach、Sabine Zitzmann-Kolbe、Matthias Friebe、Ludger M. Dinkelborg、Keith Graham

  DOI：10.1016/j.bmc.2012.11.049

  日期：2013.2

  The [F-18]fluorocyclobutyl group has the potential to be a metabolically stable prosthetic group for PET tracers. The synthesis of the radiolabeling precursor cis-cyclobutane-1,3-diyl bis(toluene-4-sulfonate) 8 was obtained from epibromohydrin in 7 steps (2% overall yield). The radiolabeling of this precursor 8 and its conjugation to L-tyrosine as a model system was successfully achieved to give the new non-natural amino acid 3-[F-18]fluorocyclobutyl-L-tyrosine (L-3-[F-18]FCBT) [F-18] 17 in 8% decay-corrected yield from the non-carrier-added [F-18] fluoride. L-3-[F-18] FCBT was investigated in vitro in different cancer cell lines to determine the uptake and stability. The tracer [F-18] 17 showed a time dependent uptake into different tumor cell lines (A549, NCI-H460, DU145) with the best uptake of 5.8% injected dose per 5 x 10(5) cells after 30 min in human lung carcinoma cells A549. The stability of L-3-[F-18] FCBT in human and rat plasma and the stability of the non-radioactive L-3-FCBT in rat hepatocytes were both found to be excellent. These results show that the non-natural amino acid L-3-[F-18] FCBT is a promising metabolically stable radiotracer for positron emission tomography. (C) 2012 Elsevier Ltd. All rights reserved.