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

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dc.contributor.authorZhang, Ben_AU
dc.contributor.authorPascali, Gen_AU
dc.contributor.authorWyatt, NAen_AU
dc.contributor.authorMatesic, Len_AU
dc.contributor.authorKlenner, MAen_AU
dc.contributor.authorSia, TRen_AU
dc.contributor.authorGuastella, AJen_AU
dc.contributor.authorMassi, Men_AU
dc.contributor.authorRobinson, AJen_AU
dc.contributor.authorFraser, BHen_AU
dc.date.accessioned2021-08-10T02:19:02Zen_AU
dc.date.available2021-08-10T02:19:02Zen_AU
dc.date.issued2018-06-20en_AU
dc.date.statistics2021-08-10en_AU
dc.description.abstractFluorine-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. © 2018 John Wiley & Sons, Inc.en_AU
dc.identifier.citationZhang, B., Pascali, G., Wyatt, N., Matesic, L., Klenner, M. A., Sia, T. R., Guastella, A. J., Massi, M., Robinson, A. J. & Fraser, B. H. (2018). Synthesis, bioconjugation and stability studies of [18F]ethenesulfonyl fluoride. Journal of Labelled Compounds and Radiopharmaceuticals, 61(11), 847-856. doi:10.1002/jlcr.3667en_AU
dc.identifier.issn1099-1344en_AU
dc.identifier.issue11en_AU
dc.identifier.journaltitleJournal of Labelled Compounds and Radiopharmaceuticalsen_AU
dc.identifier.pagination847-856en_AU
dc.identifier.urihttps://doi.org/10.1002/jlcr.3667en_AU
dc.identifier.urihttps://apo.ansto.gov.au/dspace/handle/10238/11294en_AU
dc.identifier.volume61en_AU
dc.language.isoenen_AU
dc.publisherJohn Wiley & Sons, Incen_AU
dc.subjectFluorine 18en_AU
dc.subjectLabellingen_AU
dc.subjectPeptidesen_AU
dc.subjectProteinsen_AU
dc.subjectMoleculesen_AU
dc.subjectYieldsen_AU
dc.subjectTracer techniquesen_AU
dc.subjectAmino acidsen_AU
dc.subjectCarriersen_AU
dc.subjectPositron computed tomographyen_AU
dc.titleSynthesis, bioconjugation and stability studies of [18F]ethenesulfonyl fluorideen_AU
dc.typeJournal Articleen_AU
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