ArticleChemMedChem2008
D-(+)-iso-methanocarbathymidine: a high-affinity substrate for herpes simplex virus 1 thymidine kinase.
Article in ChemMedChem, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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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
6 citing papers in PubMed, 8 citations in OpenAlex.
- Synthesis and Evaluation of Artificial Nucleic Acid Bearing an Oxanorbornane Scaffold.Molecules (Basel, Switzerland) · 2020Article
- Construction of an isonucleoside on a 2,6-dioxobicyclo[3.2.0]-heptane skeleton.Molecules (Basel, Switzerland) · 2015Article
- Highlights in antiviral drug research: antivirals at the horizon.Medicinal research reviews · 2013Review
- Antiviral activity of diarylheptanoid stereoisomers against respiratory syncytial virus in vitro and in vivo.Journal of natural medicines · 2013Article
- The effects of RNase H inhibitors and nevirapine on the susceptibility of HIV-1 to AZT and 3TC.Virology · 2011Article
- 4'-C-methyl-2'-deoxyadenosine and 4'-C-ethyl-2'-deoxyadenosine inhibit HIV-1 replication.Antimicrobial agents and chemotherapy · 2011Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
Abstract
The stereoselective syntheses of the (+)-D and (-)-L enantiomers of iso-methanocarbathymidine (iso-MCT) was achieved through two independent linear approaches that converged on two antipodal enantiomers, common to a key precursor used in the synthesis of racemic iso-MCT. In the study reported herein we identified (+)-3 [D-(+)-iso-MCT] as the active enantiomer that was exclusively recognized by the herpes simplex virus 1 thymidine kinase (HSV1-tk), as was predicted by molecular modeling. For this purpose, a human osteosarcoma (HOS) cell line modified to contain and express HSV1-tk from herpes simplex virus 1 (HSV1) was used to determine the cytotoxicity of the compounds by an assay that measures the level of ATP in the cells. The work demonstrates that changes in the substitution pattern of rigid bicyclo[3.1.0]hexane nucleosides, which, relative to normal nucleosides, appear unconventional, can lead to the spatial optimization of pharmacophores and vastly improved substrate recognition.
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Registered trials
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