18F-Fluorination of Unactivated C-H Bonds in Branched Aliphatic Amino Acids: Direct Synthesis of Oncological Positron Emission Tomography Imaging Agents

J Am Chem Soc. 2017 Mar 15;139(10):3595-3598. doi: 10.1021/jacs.6b11533. Epub 2017 Mar 1.

Abstract

A mild and selective photocatalytic C-H 18F-fluorination reaction has been developed that provides direct access to 18F-fluorinated amino acids. The biodistribution and uptake of three 18F-labeled leucine analogues via LAT1 mediated transport in several cancer cell lines is reported. Positron emission tomography imaging of mice bearing PC3 (prostate) or U87 (glioma) xenografts using 5-[18F]-fluorohomoleucine showed high tumor uptake and excellent tumor visualization, highlighting the utility of this strategy for rapid tracer discovery for oncology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Animals
  • Fluorine Radioisotopes
  • Glioma / diagnostic imaging*
  • Halogenation
  • Humans
  • Male
  • Mice
  • Molecular Conformation
  • Neoplasms, Experimental / diagnostic imaging
  • Positron-Emission Tomography*
  • Prostatic Neoplasms / diagnostic imaging*
  • Radioactive Tracers
  • Radiopharmaceuticals / chemistry*

Substances

  • Amino Acids
  • Fluorine Radioisotopes
  • Radioactive Tracers
  • Radiopharmaceuticals