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

Jonathan McConathy, Dong Zhou, Stephany E. Shockley, Lynne A. Jones, Elizabeth A. Griffin, Hsiaoju Lee, Susan J. Adams, Robert H. Mach

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)329-342
Number of pages14
JournalMolecular Imaging
Volume9
Issue number6
DOIs
StatePublished - Nov 1 2010

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