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    Synthesis, bioconjugation and stability studies of [18F]ethenesulfonyl fluoride

    272206.pdf (1.313Mb)
    Access Status
    Open access
    Authors
    Zhang, B.
    Pascali, G.
    Wyatt, N.
    Matesic, L.
    Klenner, M.
    Sia, T.
    Guastella, A.
    Massi, Massimiliano
    Robinson, A.
    Fraser, B.
    Date
    2018
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Zhang, B. and Pascali, G. and Wyatt, N. and Matesic, L. and Klenner, M. and Sia, T. and Guastella, A. et al. 2018. Synthesis, bioconjugation and stability studies of [18F]ethenesulfonyl fluoride Journal of Labelled Compounds and Radiopharmaceuticals. 61 (11): pp. 847-856.
    Source Title
    Journal of Labelled Compounds and Radiopharmaceuticals
    DOI
    10.1002/jlcr.3667
    ISSN
    0362-4803
    School
    School of Molecular and Life Sciences (MLS)
    URI
    http://hdl.handle.net/20.500.11937/72165
    Collection
    • Curtin Research Publications
    Abstract

    Fluorine-18 labelled prosthetic groups (PGs) are often necessary for radiolabelling sensitive biological molecules such as peptides and proteins. Several shortcomings, however, often diminish the final yield of radiotracer. In an attempt to provide higher yielding and operationally efficient tools for radiolabelling biological molecules, we describe herein the first radiochemical synthesis of [18F]ethenesulfonyl fluoride ([18F]ESF) and its Michael conjugation with amino acids and proteins. The synthesis of [18F]ESF was optimised using a microfluidic reactor under both carrier-added (c.a.) and no-carrier-added (n.c.a.) conditions, affording, in a straightforward procedure, 30-50% radiochemical yield (RCY) for c.a. [18F]ESF and 60-70% RCY for n.c.a. [18F]ESF. The conjugation reactions were performed at room temperature using 10 mg/mL precursor in aqueous/organic solvent mixtures for 15 min. The radiochemical stability of the final conjugates was evaluated in injectable formulation and rat serum, and resulted strongly substrate dependent and generally poor in rat serum. Therefore, in this work we have optimised a straightforward synthesis of [18F]ESF and its Michael conjugation with model compounds, without requiring chromatographic purification. However, given the general low stability of the final products, further studies will be required for improving conjugate stability, before assessing the use of this PG for PET imaging.

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