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One Step Radiosynthesis of 6-[18F]Fluoronicotinic Acid 2,3,5,6-Tetrafluorophenyl Ester ([18F]F-Py-TFP): A New Prosthetic Group for Efficient Labeling of Biomolecules with Fluorine-18

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    One Step Radiosynthesis of 6-[18F]Fluoronicotinic Acid 2,3,5,6-Tetrafluorophenyl Ester ([18F]F-Py-TFP): A New Prosthetic Group for Efficient Labeling of Biomolecules with Fluorine-18
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    † Department of Pharmaceutics and Biopharmaceutics, Institute of Pharmacy, University of Tromsø, N-9037 Tromsø, Norway
    ‡ GE Healthcare MDx R&D, Nycoveien 2, NO-0401 Oslo, Norway
    *To whom correspondence should be addressed. Phone: +47 41517119. Fax: +47 23186014. E-mail: [email protected]
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2010, 53, 4, 1732–1740
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    https://doi.org/10.1021/jm9015813
    Published January 20, 2010
    Copyright © 2010 American Chemical Society
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    Abstract

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    The labeling of biomolecules for positron emission tomography (PET) with no-carrier-added fluorine-18 is almost exclusively accomplished using prosthetic groups in a two step procedure. The inherent complexity of the process renders full automation a challenge and leads to protracted synthesis times. Here we describe a new 18F-labeled prosthetic group based on nicotinic acid tetrafluorophenyl ester. Reaction of [18F]fluoride at 40 °C with the trimethylammonium precursor afforded 6-[18F]fluoronicotinic acid tetrafluorophenyl ester ([18F]F-Py-TFP) directly in 60−70% yield. [18F]F-Py-TFP was conveniently purified by Sep-Pak cartridge prior to incubation with a peptide containing the RGD sequence. The desired conjugate was formed rapidly and in good yields. An in vitro receptor-binding assay for the integrin αvβ3 was established to explore competition with peptide and peptidomimetic prepared from F-Py-TFP with 125I-echistatin. The nonradioactive conjugates were found to possess high binding affinities with calculated Ki values in the low nanomolar range.

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    HPLC conditions, extended radio-HPLC analytical data, synthesis conditions, affinity measurement, high resolution LC−MS, HPLC spectra, and NMR spectrum of 4. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Med. Chem. 2010, 53, 4, 1732–1740
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