Synthesis of [F-18]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC): a PET tracer for tumor delineation

Abstract

Fluorine‐18 labeled 1‐amino‐3‐fluorocyclobutane‐1‐carboxylic acid (FACBC), a new tumor‐avid amino acid, was synthesized for positron emission tomography. [18F]FACBC was prepared with high specific activity by nucleophilic displacement with an overall radiochemical yield of 12% (EOB). Synthesis of the triflate precursor was accomplished in nine steps starting from the reaction of benzyl bromide with epichlorohydrin which gave 1‐chloro‐2‐benzyloxy‐3‐brompropane. A key step involves conversion of 3‐benzyloxy‐cyclobutane‐1,1‐dicarboxylate diamide to a mixture of diastereomeric 2‐benzyloxycyclobutane hydantoins. Copyright © 1999 John Wiley & Sons, Ltd.

Distinguishing Progression from Pseudoprogression in Glioblastoma Using18F-Fluciclovine PET

“…PET and DSC perfusion imaging were found to have added value in some studies (34,48,49), but these consisted of heterogeneous cohorts with grades 2-4 glioma, and the final diagnosis was based on histology in only a subset of patients. Our results showed that the accuracy of DSC MRI was comparable to that observed in prior studies, and multiparametric analysis of PET and MRI provided improved accuracy in our study, consistent with prior 18 F-FET studies (34,47,49).…”

“…Conversely, normalization of SUV max to the pituitary gland showed similar accuracy to SUV max in differentiation of TP/mixed TP from pseudoprogression. Previous studies with 18 F-FET demonstrated the usefulness of a time-activity curve with curve pattern II or III and a TTP of less than 45 min for differentiating TP from treatment-related changes (34,35,50). In our study, we did not find TTP and time-activity curve patterns to be useful because almost all patients demonstrated a type II (plateau) pattern, consistent with a prior study on pretreatment glioma (17).…”

“…In this study, we demonstrated that 18 F-fluciclovine PET can accurately differentiate pseudoprogression from TP/mixed TP in glioblastoma patients after chemoradiotherapy. The accuracy of 18 F-fluciclovine PET in our study is in the higher range of prior studies using 18 F-FET and 18 F-fluorodopa and higher than with 11 C-methionine PET (13,14,16,28,(33)(34)(35)(36)(37)(38)(39)(40)(41). In addition, we demonstrated that 18 F-fluciclovine PET has higher accuracy than advanced MRI sequences and that combining 18 F-fluciclovine PET with DSC perfusion MRI resulted in even better performance for differentiation between TP/mixed TP and pseudoprogression.…”

Quantitative PET imaging and modeling of molecular blood-brain barrier permeability

“…16,17,23 The method was also able to accurately estimate an extraction fraction equal or close to 100% for the freely diffused tracer 11 C-butanol 16 and a small extraction fraction for 18 F-fluciclovine, the latter known to have low uptake in the brain. 34,63 Second, FDG BBB PS in healthy subjects was also comparable to those reported in the literature by other methods. 12,13 Our observed negative association of FDG BBB PS with age is concordant with evidence that the expression of GLUT1 at the BBB decreases with age.…”

18F-FACBC and 18F-FDG PET/MRI in the evaluation of 3 patients with primary central nervous system lymphoma: a pilot study

“…2 and Table 2 ). The high 18 F-FACBC lesion contrast was a result of a very low 18 F-FACBC uptake in normal brain tissue, consistent with findings from previous BM and glioma studies (Tsuyuguchi et al 2017 ; Kondo et al 2016 ; Wakabayashi et al 2017 ; Michaud et al 2020 ; Bogsrud et al 2019 ; Karlberg et al 2017 , 2019 ; Johannessen et al 2021 ; Parent et al 2020 ; Shoup et al 1999 ; Øen et al 2022 ). This is likely due to slightly different 18 F-FACBC transport mechanisms across the BBB compared to other AA-PET tracers.…”