Synthesis, Radiolabeling, and Biological Evaluation of the trans-Stereoisomers of 1‑Amino-3-(fluoro-18F)-4-fluorocyclopentane-1-carboxylic Acid as PET Imaging Agents

The enantiomeric non-natural cyclic amino acids (3R,4R)-1-amino-3-fluoro-4-(fluoro-18F)­cyclopentane-1-carboxylic acid and (3S,4S)-1-amino-3-fluoro-4-(fluoro-18F)­cyclopentane-1-carboxylic acid ([ 18 F]­5) have been prepared as a racemic mixture in 1.3% decay corrected radiochemical yield and in gre...

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Published inACS pharmacology & translational science Vol. 4; no. 3; pp. 1195 - 1203
Main Authors Pickel, Thomas C, Pashikanti, Gouthami, Voll, Ronald J, Yu, Weiping, Zhang, Zhaobin, Nye, Jonathon A, Bacsa, John, Olson, Jeffrey J, Liebeskind, Lanny S, Goodman, Mark M
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 11.06.2021
Subjects
cyclic-AA
9L
microPET
DU145
U87
F-18
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Summary:The enantiomeric non-natural cyclic amino acids (3R,4R)-1-amino-3-fluoro-4-(fluoro-18F)­cyclopentane-1-carboxylic acid and (3S,4S)-1-amino-3-fluoro-4-(fluoro-18F)­cyclopentane-1-carboxylic acid ([ 18 F]­5) have been prepared as a racemic mixture in 1.3% decay corrected radiochemical yield and in greater than 99% radiochemical purity. [ 18 F]­5 is transported primarily via system L with some transport occurring via system ASC, as assessed in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells. In rats bearing intracranial 9L gliosarcoma, [ 18 F]­5 gave tumor to contralateral brain tissue ratios of up to 2.8. Biodistribution studies in healthy rats demonstrated that bladder accumulation is delayed until 10 min postinjection.
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ISSN:2575-9108
2575-9108
DOI:10.1021/acsptsci.1c00062