ArticleNature communications2015
Lipophilic prodrugs of nucleoside triphosphates as biochemical probes and potential antivirals.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
35 citing papers in PubMed.
- Triphosphate and diphosphate nucleoside prodrugs: broadening the therapeutic potential of nucleoside-based treatments.RSC medicinal chemistry · 2026Review
- Membrane-Permeable Nucleoside T-1106 Diphosphate and Triphosphate Analogues as Antiviral Pronucleotides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Design, structure-based optimization and antiviral evaluation of potent inhibitors for the macrodomain Mac1 of SARS-CoV-2.Nature communications · 2026Article
- Design, synthesis, and X-ray structural studies of potent SARS-CoV-2 Mpro inhibitors containing tetrahydroisoquinoline-3-carboxamides as P2 ligands.RSC medicinal chemistry · 2026Article
- Controlled Delivery and Light-Induced Release of Magic Spot Nucleotides in Escherichia coli.Angewandte Chemie (International ed. in English) · 2026Article
- Live-Cell RNA Imaging via Clickable TriPPPro Nucleotide Reporters.Angewandte Chemie (International ed. in English) · 2026Article
- The Interactions of Anti-HIV Pronucleotides with a Model Phospholipid Membrane.Molecules (Basel, Switzerland) · 2024Article
- An "AND" logic gate-based supramolecular therapeutic nanoplatform for combatting drug-resistant non-small cell lung cancer.Science advances · 2024Article
- Metabolic RNA labeling in non-engineered cells following spontaneous uptake of fluorescent nucleoside phosphate analogues.Nucleic acids research · 2024Article
- MASTER-NAADP: a membrane permeable precursor of the CaNature communications · 2024Article
- Intracellular delivery and deep tissue penetration of nucleoside triphosphates using photocleavable covalently bound dendritic polycations.Chemical science · 2024Article
- Antiviral Activity of Lipophilic Nucleoside Tetraphosphate Compounds.Journal of medicinal chemistry · 2024Article
- Bioorthogonal Chemistry in Cellular Organelles.Topics in current chemistry (Cham) · 2023Review
- Lipophilic Nucleoside Triphosphate Prodrugs of Anti-HIV Active Nucleoside Analogs as Potential Antiviral Compounds.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- The Application of Prodrugs as a Tool to Enhance the Properties of Nucleoside Reverse Transcriptase Inhibitors.Viruses · 2023Review
- Cationic Polymers Enable Internalization of Negatively Charged Chemical Probes into Bacteria.ACS chemical biology · 2023Article
- Epigenetic Pyrimidine Nucleotides in Competition with Natural dNTPs as Substrates for Diverse DNA Polymerases.ACS chemical biology · 2022Article
- The First 5'-Phosphorylated 1,2,3-Triazolyl Nucleoside Analogues with Uracil and Quinazoline-2,4-Dione Moieties: A Synthesis and Antiviral Evaluation.Molecules (Basel, Switzerland) · 2022Article
- Interrogating the transcriptome with metabolically incorporated ribonucleosides.Molecular omics · 2021Review
- Cellular delivery of dinucleotides by conjugation with small molecules: targeting translation initiation for anticancer applications.Chemical science · 2021Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The antiviral activity of nucleoside reverse transcriptase inhibitors is often limited by ineffective phosphorylation. We report on a nucleoside triphosphate (NTP) prodrug approach in which the γ-phosphate of NTPs is bioreversibly modified. A series of TriPPPro-compounds bearing two lipophilic masking units at the γ-phosphate and d4T as a nucleoside analogue are synthesized. Successful delivery of d4TTP is demonstrated in human CD4(+) T-lymphocyte cell extracts by an enzyme-triggered mechanism with high selectivity. In antiviral assays, the compounds are potent inhibitors of HIV-1 and HIV-2 in CD4(+) T-cell (CEM) cultures. Highly lipophilic acyl residues lead to higher membrane permeability that results in intracellular delivery of phosphorylated metabolites in thymidine kinase-deficient CEM/TK(-) cells with higher antiviral activity than the parent nucleoside.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.