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- W2000473242 abstract "A novel approach to the intracellular delivery of aryl phosphates has been developed that utilizes a phosphoramidate-based prodrug approach. The prodrugs contain an ester group that undergoes reductive activation intracellularly with concomitant expulsion of a phosphoramidate anion. This anion undergoes intramolecular cyclization and hydrolysis to generate aryl phosphate exclusively with a t1/2 = ∼20 min. Phosphoramidate prodrugs (8−10) of phosphate-containing peptidomimetics that target the SH2 domain were synthesized. Evaluation of these peptidomimetic prodrugs in a growth inhibition assay and in a cell-based transcriptional assay demonstrated that the prodrugs had IC50 values in the low micromolar range. Synthesis of phosphorodiamidate analogues containing a P−NH−Ar linker (16−18) was also carried out in the hope that the phosphoramidates released might be phosphatase-resistant. Comparable activation rates and cell-based activities were observed for these prodrugs, but the intermediate phosphoramidate dianion underwent spontaneous hydrolysis with a t1/2 = ∼30 min." @default.
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- W2000473242 date "2006-05-11" @default.
- W2000473242 modified "2023-09-25" @default.
- W2000473242 title "Design and Synthesis of Phosphotyrosine Peptidomimetic Prodrugs" @default.
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- W2000473242 doi "https://doi.org/10.1021/jm060142p" @default.
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