Radiosynthesis of 11-[18F]fluoroundecyltriphenylphosphonium (MitoF) as a potential mitochondria-specific positron emission tomography radiotracer

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 56; no. 14; pp. 717 - 721
• Main Authors: Li, L., Brichard, L., Larsen, L., Menon, D. K., Smith, R. A. J., Murphy, M. P., Aigbirhio, F. I.
• Format: Journal Article
• Language: English; French; German
• Published: HOBOKEN Blackwell Publishing Ltd 01.12.2013; Wiley; Wiley Subscription Services, Inc
• Subjects: Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Fluorine Radioisotopes - chemistry; fluorine-18; imaging; Isotope Labeling; Life Sciences & Biomedicine; mitochondria; Mitochondria - metabolism; MitoF; Organophosphorus Compounds - chemical synthesis; PET; Pharmacology & Pharmacy; Physical Sciences; Positron-Emission Tomography; Radiopharmaceuticals - chemical synthesis; Science & Technology; triphenylphosphonium; AGENT; THERAPEUTICS; MitoF; fluorine-18; TARGETED ANTIOXIDANT MITOQ; THERAPY; mitochondria; DISEASE; triphenylphosphonium; imaging; CATION; PET
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/jlcr.3109

Changes in the magnitude of the mitochondrial membrane potential occur in a range of important pathologies. To assess changes in membrane potential in patients, we set out to develop an improved mitochondria‐targeted positron emission tomography probe comprising a lipophilic triphenylphosphonium cation attached to a fluorine‐18 radionuclide via an 11‐carbon alkyl chain, which is well‐established to effectively transport to and localise within mitochondria. Here, we describe the radiosynthesis of this probe, 11‐[18F]fluoroundecyl‐triphenylphosphonium (MitoF), from no‐carrier‐added [18F]fluoride and a fully automated synthetic protocol to prepare it in good radiochemical yields (2–3 GBq at end‐of‐synthesis) and radiochemical purity (97–99%). Copyright © 2013 John Wiley & Sons, Ltd. Radiosynthesis of the probe, 11‐[18F]fluoroundecyl‐triphenylphosphonium (MitoF), from no‐carrier‐added [18F]fluoride.