Stereoselective synthesis and biological evaluation of syn-1-amino-3-[18F]fluorocyclobutyl-1-carboxylic acid as a potential positron emission tomography brain tumor imaging agent |
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| Authors: | Weiping Yu Larry Williams Vernon M. Camp Eugene Malveaux Jeffrey J. Olson Mark M. Goodman |
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| Affiliation: | 1. Department of Radiology, School of Medicine, Emory University, Atlanta, GA 30322, USA;2. Department of Neurosurgery, School of Medicine, Emory University, Atlanta, GA 30322, USA |
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| Abstract: | Amino acid syn-1-amino-3-fluoro-cyclobutyl-1-carboxylic acid (syn-FACBC) 12, the isomer of anti-FACBC, has been selectively synthesized and [18F] radiofluorinated in 52% decay-corrected yield using no-carrier-added [18F]fluoride. The key step in the synthesis of the desired isomer involved stereoselective reduction using lithium alkylborohydride/zinc chloride, which improved the ratio of anti-alcohol to syn-alcohol from 17:83 to 97:3. syn-FACBC 12 entered rat 9L gliosarcoma cells primarily via L-type amino acid transport in vitro with high uptake of 16% injected dose per 5 × 105 cells. Biodistribution studies in rats with 9L gliosarcoma brain tumors demonstrated high tumor to brain ratio of 12:1 at 30 min post injection. In this model, amino acid syn-[18F]FACBC 12 is a promising metabolically based radiotracer for positron emission tomography brain tumor imaging. |
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