Synthesis of [18F]-labeled (2-(2-fluoroethoxy)ethyl)tris(4-methoxyphenyl)phosphonium cation as a potential agent for positron emission tomography myocardial imaging

Nuclear Medicine and Biology
Dong-Yeon KimJung-Joon Min

Abstract

Established radiotracers for positron emission tomography (PET) myocardial perfusion study are commonly labeled with short-lived radio-isotopes that limit their widespread clinical use. Thus, we synthesized (2-(2-[(18)F]fluoroethoxy)ethyl)tris(4-methoxyphenyl)phosphonium salt ([(18)F]FETMP) as a novel myocardial perfusion agent that penetrates the hydrophobic barriers of the plasma and mitochondrial membranes and accumulate in mitochondria of cardiomyocytes in response to the negative inner-transmembrane potentials. The [(18)F]FETMP was synthesized via two-step nucleophilic substitution reactions of no-carrier-added [(18)F]fluoride with the precursor 2,2'-oxybis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate) in the presence of Kryptofix 2.2.2 and K(2)CO(3). The [(18)F]FETMP accumulation was measured in cell culture with rat embryonic cardiomyoblast (H9c2) and mouse normal fibroblast (NIH/3T3) cell lines. The mitochondrial membrane potential-dependent cellular uptake of [(18)F]FETMP was further assessed using the H9c2 cells treated with carbonyl cyanide m-chlorophenylhydrazone (CCCP) which is a protonophore that selectively abolishes the mitochondrial membrane potential. Biodistribution and micro-PET studies were performed in nor...Continue Reading

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Citations

Sep 23, 2014·Seminars in Nuclear Medicine·Jamshid Maddahi, René R S Packard
Aug 20, 2016·Nuclear Medicine and Molecular Imaging·Dong-Yeon Kim, Jung-Joon Min
Mar 31, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tiantian Mou, Xianzhong Zhang
Jun 14, 2017·Chemical Society Reviews·Dion van der BornDanielle J Vugts
Jun 24, 2017·BioMed Research International·Jinhui LiYou Zhou
Oct 23, 2018·Medicina·Eglė KazakauskaitėRenaldas Jurkevičius
Aug 14, 2018·Nuclear Medicine and Molecular Imaging·Dong-Yeon KimHee-Seung Bom
Jun 13, 2015·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Dong-Yeon KimJung-Joon Min
Aug 24, 2021·Nuclear Medicine and Molecular Imaging·Sang-Geon ChoIhnho Cho

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