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Synthesis and biological evaluation of a new acyclic pyrimidine derivative as a probe for imaging herpes simplex virus type 1 thymidine kinase gene expression.

ABSTRACT: With the idea of finding a more selective radiotracer for imaging herpes simplex virus type 1 thymidine kinase (HSV1-tk) gene expression by means of positron emission tomography (PET), a novel [¹?F]fluorine radiolabeled pyrimidine with 4-hydroxy-3-(hydroxymethyl)butyl side chain at N-1 (HHB-5-[¹?F]FEP) was prepared and evaluated as a potential PET probe. Unlabeled reference compound, HHB-5-FEP, was synthesized via a five-step reaction sequence starting from 5-(2-acetoxyethyl)-4-methoxypyrimidin-2-one. The radiosynthesis of HHB-[¹?F]-FEP was accomplished by nucleophilic radiofluorination of a tosylate precursor using [¹?F]fluoride-cryptate complex in 45% ± 4 (n = 4) radiochemical yields and high purity (>99%). The biological evaluation indicated the feasibility of using HHB-5-[¹?F]FEP as a PET radiotracer for monitoring HSV1-tk expression in vivo.

SUBMITTER: Mescic A 

PROVIDER: S-EPMC6270388 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Synthesis and biological evaluation of a new acyclic pyrimidine derivative as a probe for imaging herpes simplex virus type 1 thymidine kinase gene expression.

Meščić Andrijana A   Betzel Thomas T   Müller Adrienne A   Slavik Roger R   Cermak Stjepko S   Raić-Malić Silvana S   Ametamey Simon M SM  

Molecules (Basel, Switzerland) 20130719 7

With the idea of finding a more selective radiotracer for imaging herpes simplex virus type 1 thymidine kinase (HSV1-tk) gene expression by means of positron emission tomography (PET), a novel [¹⁸F]fluorine radiolabeled pyrimidine with 4-hydroxy-3-(hydroxymethyl)butyl side chain at N-1 (HHB-5-[¹⁸F]FEP) was prepared and evaluated as a potential PET probe. Unlabeled reference compound, HHB-5-FEP, was synthesized via a five-step reaction sequence starting from 5-(2-acetoxyethyl)-4-methoxypyrimidin-  ...[more]

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