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dc.contributor.author
Meščić, Andrijana
dc.contributor.author
Krištafor, Svjetlana
dc.contributor.author
Novakovic, Ivana
dc.contributor.author
Osmanović, Amar
dc.contributor.author
Müller, Ursina
dc.contributor.author
Završnik, Davorka
dc.contributor.author
Ametamey, Simon M.
dc.contributor.author
Scapozza, Leonardo
dc.contributor.author
Raić-Malić, Silvana
dc.date.accessioned
2019-06-27T14:27:57Z
dc.date.available
2017-06-10T17:53:30Z
dc.date.available
2019-06-27T14:27:57Z
dc.date.issued
2013-04-02
dc.identifier.issn
1420-3049
dc.identifier.other
10.3390/molecules18055104
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/67864
dc.identifier.doi
10.3929/ethz-b-000067864
dc.description.abstract
The efficient syntheses of 5-(2-hydroxyethyl)- and 5-(3-hydroxypropyl)-substituted pyrimidine derivatives bearing 2,3-dihydroxypropyl, acyclovir-, ganciclovir- and penciclovir-like side chains are reported. A synthetic approach that included the alkylation of an N-anionic-5-substituted pyrimidine intermediate (method A) provided the target acyclonucleosides in significantly higher overall yields in comparison to those obtained by method B using sylilation reaction. The phosphorylation assays of novel compounds as potential substrates for thymidine kinase of herpes simplex virus type 1 (HSV-1 TK) showed that solely pyrimidine 5-substituted acyclonucleosides with a penciclovir-like side chain acted as a fraudulent substrates of HSV-1 TK. Moreover, the uracil derivative with penciclovir-like side chain with less bulky 2-hydroxyethyl substituent at C-5 proved to be a better substrate than the corresponding one with a 3-hydroxypropyl substituent. Therefore, this acyclonucleoside was selected as a lead compound for the development of a positron emission tomography HSV-1 TK activity imaging agent.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
MDPI
en_US
dc.rights.uri
http://creativecommons.org/licenses/by/3.0/
dc.subject
Acyclic nucleoside analogues
en_US
dc.subject
5-substituted pyrimidines
en_US
dc.subject
Herpes simplex
en_US
dc.subject
Virus type 1 thymidine kinase (HSV-1 TK)
en_US
dc.subject
Positron emission tomography (PET)
en_US
dc.title
C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluation
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution 3.0 Unported
ethz.journal.title
Molecules
ethz.journal.volume
18
en_US
ethz.journal.issue
5
en_US
ethz.journal.abbreviated
Molecules
ethz.pages.start
5104
en_US
ethz.pages.end
5124
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.wos
ethz.publication.place
Basel
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02534 - Institut für Pharmazeutische Wiss. / Institute of Pharmaceutical Sciences::03688 - Schibli, Roger / Schibli, Roger
en_US
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02534 - Institut für Pharmazeutische Wiss. / Institute of Pharmaceutical Sciences::03688 - Schibli, Roger / Schibli, Roger
ethz.date.deposited
2017-06-10T17:54:51Z
ethz.source
ECIT
ethz.identifier.importid
imp593650ad63fb861144
ethz.ecitpid
pub:107940
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2017-07-19T11:01:51Z
ethz.rosetta.lastUpdated
2024-02-02T08:23:45Z
ethz.rosetta.versionExported
true
ethz.COinS
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