Open AccessSynthesis, Radiolabeling, and Biological Evaluation of the trans-Stereoisomers of 1-Amino-3-(fluoro-18F)-4-fluorocyclopentane-1-carboxylic Acid as PET Imaging Agents
Author(s) -
Thomas C. Pickel,
Pashikanti Gouthami,
Ronald J. Voll,
Winston Yu,
Zhaobin Zhang,
Jonathon A. Nye,
John Bacsa,
Jeffrey J. Olson,
Lanny S. Liebeskind,
Mark M. Goodman
Publication year - 2021
Publication title -
acs pharmacology and translational science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.271
H-Index - 10
ISSN - 2575-9108
DOI - 10.1021/acsptsci.1c00062
Subject(s) - gliosarcoma , du145 , chemistry , biodistribution , enantiomer , carboxylic acid , amino acid , radiochemistry , yield (engineering) , stereochemistry , prostate , glioblastoma , biochemistry , cancer research , medicine , in vitro , lncap , materials science , cancer , metallurgy
The enantiomeric non-natural cyclic amino acids (3 R ,4 R )-1-amino-3-fluoro-4-(fluoro- 18 F)cyclopentane-1-carboxylic acid and (3 S ,4 S )-1-amino-3-fluoro-4-(fluoro- 18 F)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.