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Radiosynthesis and preliminary biological evaluation of a new 18 F‐labeled triethylene glycol derivative of triphenylphosphonium
Author(s) -
Tominaga Takahiro,
Ito Hiroaki,
Ishikawa Yoichi,
Iwata Ren,
Ishiwata Kiichi,
Furumoto Shozo
Publication year - 2016
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3379
Subject(s) - chemistry , triethylene glycol , hydrobromide , biodistribution , bromide , radiosynthesis , radiochemistry , derivative (finance) , in vitro , nuclear chemistry , polymer chemistry , nuclear medicine , biochemistry , positron emission tomography , organic chemistry , medicine , economics , financial economics
Delocalized lipophilic cations such as [ 18 F]fluorobenzyltriphenylphosphonium ([ 18 F]FBnTP) can accumulate in mitochondria and have been used in myocardial perfusion imaging (MPI). In this study, we established a simplified method for [ 18 F]FBnTP synthesis using triphenylphosphine hydrobromide (PPh 3 •HBr) without preparing an intermediate that contains benzyl bromide structure. Applying this new method, we synthesized and evaluated a novel 18 F‐labeled PEGylated BnTP derivative ([ 18 F]FPEGBnTP). In vitro cellular uptake study demonstrated that [ 18 F]FPEGBnTP accumulated in cells in proportion to the relative intensity of mitochondrial membrane potential. Biodistribution study revealed that the heart : liver uptake ratio of [ 18 F]FPEGBnTP (4.00 at 60 min) was superior to that of [ 18 F]FBnTP (1.50 at 60 min). However, [ 18 F]FPEGBnTP showed slow blood clearance and high radioactivity uptake in bone at 120‐min post‐injection. These results imply the possibility of [ 18 F]FPEGBnTP being used as a MPI agent. However, there is a need of further structural optimization and flow‐dependent uptake study.