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Synthesis and biological evaluation of a lipophilic, fluorine-18-labeled 5-ethynyl-2′-deoxyuridine derivative

✍ Scribed by Satish K. Chitneni; Tom De Ruymaeker; Jan Balzarini; Alfons M. Verbruggen; Guy M. Bormans

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
125 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis and preliminary biological evaluation of a lipophilic, fluorine‐18‐labeled 5‐ethynyl‐2′‐deoxyuridine derivative [^18^F]‐3 is described. Initially, 5‐ethynyl‐2′‐deoxyuridine 5 was synthesized by coupling trimethylsilyl protected acetylene to 5‐iodo‐2′‐deoxyuridine 4, followed by deprotection in alkaline conditions. Compound 5 was then reacted with 4‐(4′‐iodophenyl)phenol to give 5‐[4(4′‐hydroxyphenyl)phenyl]ethynyl‐2′‐deoxyuridine 6. Compound 6 was reacted with BrCH~2~CHF as alkylating agent to give stable or radiolabeled 3. The crude products were purified using reversed phase‐high performance liquid chromatography to obtain compound 3 and [^18^F]‐3 in 33 and 7.4% yield (decay corrected), respectively. The synthesis time to obtain pure [^18^F]‐3 was about 60 min (starting from BrCH~2~CHF). The specific radioactivity of the tracer was between 74 and 222 GBq/µmol. The log P~7.4~ of [^18^F]‐3 was found to be 2.4. However, biodistribution study in normal mice showed low uptake of the tracer in the brain. The affinity of compounds 6 and 3 for varicella‐zoster virus thymidine kinase enzyme (VZV‐TK) was examined in vitro and the results revealed that the fluorinated analog 3 has a poor affinity for the enzyme in contrast to the phenol precursor 6. Copyright © 2007 John Wiley & Sons, Ltd.

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