Journal
BIOCONJUGATE CHEMISTRY
Volume 23, Issue 3, Pages 431-437Publisher
AMER CHEMICAL SOC
DOI: 10.1021/bc2004439
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Funding
- National Research Foundation of Korea (NRF) [2011-0029941]
- Brain Korea 21 Project
- Ministry of Education, Science, and Technology
- Korean Ministry of Education, Science and Technology
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Lipophilic cations such as phosphonium salts penetrate the hydrophobic barriers of the plasma and mitochondrial membranes and accumulate in mitochondria in response to the negative inner-transmembrane potentials. Thus, as newly developed noninvasive imaging agents, [F-18]-labeled phosphonium salts may serve as molecular voltage sensor probes to investigate the role of mitochondria, particularly in myocardial disease. The present study reports the radiosynthesis of (6-fluorohexyl)triphenylphosphonium salt (3) as a potential agent for myocardial imaging by using positron emission tomography (PET). The reference compound of (6-[F-18]fluorohexyl)triphenylphosphonium salt ([F-18]3) was synthesized with 74% yield via three-step nucleophilic substitution reactions. The reference compound was radiolabeled via two-step nucleophilic substitution reactions of no-carrier-added [F-18]fluoride with the precursor hexane-1,6-diyl bis(4-methylbenzenesulfonate) in the presence of Kryptofix 2.2.2 and K2CO3. The radiolabeled compound was synthesized with 15-20% yield. The radiochemical purity was >98% by analytical HPLC, and the specific activity was >6.10-6.47 TBq/mu mol. The cellular uptake assay showed preferential uptake of [F-18]3 in cardiomyocytes. The results of biodistribution and micro-PET imaging studies of [F-18]3 in mice and rats showed preferential accumulation in the myocardium. The results suggest that this compound would be a promising candidate for myocardial imaging.
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