Lipophilic Nucleoside Triphosphate Prodrugs of Anti-HIV Active Nucleoside Analogs as Potential Antiviral Compounds.
antiviral activity
nucleoside analog
nucleoside diphosphates
nucleoside triphosphates
prodrugs
Journal
Advanced science (Weinheim, Baden-Wurttemberg, Germany)
ISSN: 2198-3844
Titre abrégé: Adv Sci (Weinh)
Pays: Germany
ID NLM: 101664569
Informations de publication
Date de publication:
26 Oct 2023
26 Oct 2023
Historique:
received:
24
08
2023
medline:
27
10
2023
pubmed:
27
10
2023
entrez:
26
10
2023
Statut:
aheadofprint
Résumé
Nucleoside analogs require three phosphorylation steps catalyzed by cellular kinases to give their triphosphorylated metabolites. Herein, the synthesis of two types of triphosphate prodrugs of different nucleoside analogs is disclosed. Triphosphates comprising: i) a γ-phosphate or γ-phosphonate bearing a bioreversible acyloxybenzyl group and a long alkyl group and ii) γ-dialkyl phosphate/phosphonate modified nucleoside triphosphate analogs. Almost selective conversion of the former TriPPPro-compounds into the corresponding γ-alkylated nucleoside triphosphate derivatives is demonstrated in CEM/0 cell extracts that proved to be stable toward further hydrolysis. The latter γ-dialkylated triphosphate derivatives lead to the slow formation of the corresponding NDPs. Both types of TriPPPro-compounds are highly potent in wild-type CEM/0 cells and more importantly, they exhibit even better activities against HIV-2 replication in CEM/TK
Identifiants
pubmed: 37884485
doi: 10.1002/advs.202306021
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2306021Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : Me1161/13-1
Organisme : Deutsche Forschungsgemeinschaft
ID : Me1161/15-1
Organisme : Deutsche Forschungsgemeinschaft
ID : Me1161/17-1
Organisme : Society of the Friendly Sons of St. Patrick for the Relief of Emigrants from Ireland
Informations de copyright
© 2023 The Authors. Advanced Science published by Wiley-VCH GmbH.
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