ArticleACS medicinal chemistry letters2019
Synthesis and Bioactivity of the Alanyl Phosphonamidate Stereoisomers Derived from a Butyrophilin Ligand.
Article in ACS medicinal chemistry letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
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Who cites it
11 citing papers in PubMed, 14 citations in OpenAlex.
- Benzoic Acid Derivatives Improve Plasma Stability of Diester Butyrophilin Ligand Prodrugs.Journal of medicinal chemistry · 2026Article
- Synthesis and evaluation of triazole-containing aryl/acyloxy prodrugs of a BTN3A1 ligand.European journal of medicinal chemistry · 2025Article
- Enhanced Plasma Stability and Potency of Aryl/Acyloxy Prodrugs of a BTN3A1 Ligand.ACS medicinal chemistry letters · 2024Article
- Diester Prodrugs of a Phosphonate Butyrophilin Ligand Display Improved Cell Potency, Plasma Stability, and Payload Internalization.Journal of medicinal chemistry · 2023Article
- Efficiency of bis-amidate phosphonate prodrugs.Bioorganic & medicinal chemistry letters · 2022Article
- Synthesis and Metabolism of BTN3A1 Ligands: Studies on Diene Modifications to the Phosphoantigen Scaffold.ACS medicinal chemistry letters · 2022Article
- Synthesis and Metabolism of BTN3A1 Ligands: Studies on Modifications of the Allylic Alcohol.ACS medicinal chemistry letters · 2021Article
- Potent double prodrug forms of synthetic phosphoantigens.Bioorganic & medicinal chemistry · 2020Article
- Metabolic Efficacy of Phosphate Prodrugs and the Remdesivir Paradigm.ACS pharmacology & translational science · 2020Review
- Structure-Activity Relationships of Butyrophilin 3 Ligands.ChemMedChem · 2020Review
- A luciferase lysis assay reveals in vivo malignant cell sensitization by phosphoantigen prodrugs.Biochemical pharmacology · 2019Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Aryloxy phosphonamidate derivatives of a butyrophilin 3A1 ligand are stimulants of Vγ9 Vδ2 T cells. However, when bonded to an aryl ester and an amine, the phosphorus is stereogenic, and past compounds were studied as racemates. To determine the impact of stereochemistry on the activity, we now have prepared phosphonate derivatives of l- and d-alanine ethyl ester, separated the diastereomers, and evaluated their biological activity as single stereoisomers. The results demonstrate that phosphonamidates substituted with l-alanine stimulate Vγ9 Vδ2 T cells at lower concentrations than the racemic glycine counterpart, while those derived from d-alanine require higher concentrations. All four diastereomers are more active than charged phosphoantigens such as HMBPP. Surprisingly, only a 2-fold difference was observed between the l-alanine phosphorus isomers, with the
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Registered trials
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