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

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

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Received: 27 May 2013; in revised form: 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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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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.

AMA Style

Meščić A, Betzel T, Müller A, Slavik R, Čermak S, Raić-Malić S, Ametamey SM. 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(7):8535-8549.

Chicago/Turabian Style

Meščić, Andrijana; Betzel, Thomas; Müller, Adrienne; Slavik, Roger; Čermak, Stjepko; Raić-Malić, Silvana; Ametamey, Simon M. 2013. "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 18, no. 7: 8535-8549.

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