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Molecules 2013, 18(7), 8535-8549; doi:10.3390/molecules18078535

Synthesis and Biological Evaluation of a New Acyclic Pyrimidine Derivative as a Probe for Imaging Herpes Simplex Virus Type 1 Thymidine Kinase Gene Expression

1
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P.O. Box 177, HR-10 000 Zagreb, Croatia
2
Center for Radiopharmaceutical Sciences, ETH Zurich (Swiss Federal Institute of Technology), Wolfgang-Pauli-Strasse 10, CH-8093 Zurich, Switzerland
*
Authors to whom correspondence should be addressed.
Received: 27 May 2013 / Revised: 12 July 2013 / Accepted: 16 July 2013 / Published: 19 July 2013
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
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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 [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-2-one. The radiosynthesis of HHB-[18F]-FEP was accomplished by nucleophilic radiofluorination of a tosylate precursor using [18F]fluoride-cryptate complex in 45% ± 4 (n = 4) radiochemical yields and high purity (>99%). The biological evaluation indicated the feasibility of using HHB-5-[18F]FEP as a PET radiotracer for monitoring HSV1-tk expression in vivo.
Keywords: acyclic pyrimidine nucleoside analogues; PCV-like side chain; fluorination; radiosynthesis; positron emission tomography (PET); HSV1-TK acyclic pyrimidine nucleoside analogues; PCV-like side chain; fluorination; radiosynthesis; positron emission tomography (PET); HSV1-TK
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Meščić, A.; Betzel, T.; Müller, A.; Slavik, R.; Čermak, S.; Raić-Malić, S.; Ametamey, S.M. Synthesis and Biological Evaluation of a New Acyclic Pyrimidine Derivative as a Probe for Imaging Herpes Simplex Virus Type 1 Thymidine Kinase Gene Expression. Molecules 2013, 18, 8535-8549.

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