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http://dx.doi.org/10.22643/JRMP.2018.4.2.57

Synthesis and biodistribution of 18F-labeled α-, β- and ω-fluorohexadecanoic acid  

Lee, Yun-Sang (Department of Nuclear Medicine, Seoul National University College of Medicine)
Kim, Young Joo (Department of Nuclear Medicine, Seoul National University College of Medicine)
Cheon, Gi Jeong (Department of Nuclear Medicine, Seoul National University College of Medicine)
Jeong, Jae Min (Department of Nuclear Medicine, Seoul National University College of Medicine)
Publication Information
Journal of Radiopharmaceuticals and Molecular Probes / v.4, no.2, 2018 , pp. 57-64 More about this Journal
Abstract
${\omega}-[^{18}F]$-Fluorohexadecanoic acid (FHA) has been used for imaging of fatty acid metabolism of myocardium. To increase retention of radiolabeled fatty acid by blocking ${\beta}$-oxidation, methyl branched analogues have been used. In this experiment, we tried to synthesize 18F-labeled ${\alpha}-$, ${\beta}-$ and ${\omega}-FHA$ for imaging of the myocardial fatty acid metabolism. We synthesized ${\alpha}-$, ${\beta}-$ and ${\omega}$-mesylated methyl hexadecanoates and labeled with $^{18}F$ by reacting with $[^{18}F]$TBAF in acetonitrile at $80^{\circ}C$ for 10 min. Methyl ester group was removed by 1 M NaOH at $80^{\circ}C$ for 5 min. The yields of ${\alpha}-[^{18}F]$ and ${\omega}-[^{18}F]FHA$ were 25.5 and 45.5%, respectively [EOS]. However, ${\beta}-[^{18}F]FHA$ was not labeled at all due to a fast elimination reaction. The biodistribution study in ICR-mice showed that ${\omega}-[^{18}F]FHA$ has higher myocardial uptake and lower liver uptake than ${\alpha}-[^{18}F]FHA$. The electron-withdrawing effect of fluorine at ${\alpha}-$ position is believed to be the major factor affecting the biodistribution.
Keywords
Myocardial imaging; Positron emission tomography; Radiolabeled fatty acid;
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