Click synthesis and biologic evaluation of (R)- and (S)-2-amino-3-[1-(2-[18F]fluoroethyl)-1H-[1,2,3]triazol-4-yl]propanoic acid for brain tumor imaging with positron emission tomography.

Academic Article


  • The (R)- and (S)-enantiomers of 2-amino-3-[1-(2-[18F]fluoroethyl)-1H-[1,2,3]triazol-4-yl]propanoic acid (4) were synthesized and evaluated in the rat 9L gliosarcoma brain tumor model using cell uptake assays, biodistribution studies, and micro-positron emission tomography (microPET). The (R)- and (S)-enantiomers of [18F]4 were radiolabeled separately using the click reaction in 57% and 51% decay-corrected yields, respectively. (S)-[18F]4 was a substrate for cationic amino acid transport and, to a lesser extent, system L transport in vitro. In vivo biodistribution studies demonstrated that (S)-[18F]4 provided higher tumor uptake and higher tumor to brain ratios (15:1 at the 30- and 60-minute time points) compared to the (R)-enantiomer (7:1 at the 30- and 60-minute time points). MicroPET studies with (S)-[18F]4 confirmed that this tracer provides good target to background ratios for both subcutaneous and intracranial 9L gliosarcoma tumors. Based on these results, the 1H-[1,2,3]triazole-substituted amino acid (S)-[18F]4 has promising PET properties for brain tumors and represents a novel class of radiolabeled amino acids for tumor imaging.
  • Published In

  • Molecular Imaging  Journal
  • Keywords

  • Alanine, Animals, Brain Neoplasms, Click Chemistry, Gliosarcoma, Humans, Positron-Emission Tomography, Propionates, Rats, Rats, Inbred F344, Subcutaneous Tissue, Time Factors, Tissue Distribution, Triazoles
  • Pubmed Id

  • 22586097
  • Author List

  • McConathy J; Zhou D; Shockley SE; Jones LA; Griffin EA; Lee H; Adams SJ; Mach RH
  • Start Page

  • 329
  • End Page

  • 342
  • Volume

  • 9
  • Issue

  • 6