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J Nucl Med. 2008; 49 (Supplement 1):299P
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Radiopharmaceutical Chemistry: New Chemistry-Other

New Chemistry-Other Posters

Capturing aqueous F-18 fluoride with an arylboronic ester for PET

Michael Adam1, Thomas Ruth1, Richard Ting2 and David Perrin2

1 TRIUMF, Vancouver, British Columbia, Canada; ; 2 Chemistry, UBC, Vancouver, British Columbia, Canada

1274

Objectives: Arylboronic acids represent potential captors of aqueous [18F]-fluoride that would conveniently provide [18F]-labeled PET-imaging agents composed of a pendant aryl-[18F]-trifluoroborate. 19F-NMR permitted the analysis of the arylboronic ester and its conversion to the aryltrifluoroborate. In addition, an 19F-containing fluorescent BODIPY permits a fluorescent corroboration of both the yield of radiolabeled aryl-[18F]-trifluoroborate as well as its aqueous stability to solvolytic fluoride exchange.

Methods: The synthesis of an [19F]-labeled fluorescent boronic acid was accomplished in essentially three steps starting with 2,4,6-trifluorobenzoic acid which was cleanly lithiated, boronated, and converted to its tetraphenylpincolate ester in approximately 50% yield. This compound was then coupled to amino-BODIPY (aminophenyldi(dimethylpyrro)methene boron difluoride). 2.8 µmoles was dissolved in 24.6 µL MeOH to which was added, 2 µL of water containing 1mCi of carrier-free [18F]-fluoride at pH 2-3, followed by 1.4 µL of a 4M [19F]-KHF2 solution to afford the product in 16.8% radiochemical yield and a specific activity of 89 µCi/µmol.

Results: F-18 fluorination of an arylboronic ester gave the corresponding aryltrifluoroborate in reasonable radiochemical yield. F-19 nmr, fuorescence, and F-18 labeling techniques confirmed the structure and stability of the resulting aryltrifluoroborate.

Conclusions: The idea of using boronic acids as captors of aqueous [18F]-fluoride is an attractive one given the simplicity of working with aqueous [18F]-fluoride and a precursor boronate ester. Here we have conclusively demonstrated that the resulting [18F]-trifluoroborate is both easily separated from both starting material and free [18F]-fluoride and stable to solvolytic defluoridation.

Research Support: This work was supported by the Canadian Institutes for Health Research.





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Right arrow Articles by Perrin, D.