Facile synthesis of para-[18F]fluorohippurate via iodonium ylide-mediated radiofluorination for PET renography

[Display omitted] para-[18F]fluorohippurate ([18F]PFH) is a renal tubular agent suitable for conducting positron emission tomography (PET) renography. [18F]PFH is currently synthesized by a four-step two-pot procedure utilizing a classical prosthetic group, N-succinimidyl-4-[18F]fluorobenzoate, foll...

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Published in:Bioorganic & medicinal chemistry letters 2016-01, Vol.26 (2), p.479-483
Main Authors: Nkepang, Gregory N., Hedrick, Andria F., Awasthi, Vibhudutta, Gali, Hariprasad
Format: Article
Language:English
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Summary:[Display omitted] para-[18F]fluorohippurate ([18F]PFH) is a renal tubular agent suitable for conducting positron emission tomography (PET) renography. [18F]PFH is currently synthesized by a four-step two-pot procedure utilizing a classical prosthetic group, N-succinimidyl-4-[18F]fluorobenzoate, followed by glycine conjugation. Considering the short half-life of fluorine-18 (110min), it is important to reduce the number of synthetic steps and overall production time for successful translation of any fluorine-18 radiopharmaceutical in to clinical practice. Here, we report a new two-step one-pot procedure using a novel spirocyclic iodonium ylide precursor for producing a dose of [18F]PFH suitable for human use in 45min including HPLC purification with an overall decay-corrected radiochemical yield of 46.4±2.9% (n=3) and radiochemical purity of >99%.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2015.11.091