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• W2511601009 abstract "Naturally occurring Nω-hydroxy-l-arginine (NOHA, 1) is the best substrate of NO synthases (NOS). The development of stable and bioavailable prodrugs would provide a pharmacologically valuable strategy for the treatment of cardiovascular diseases that are associated with endothelial dysfunction. To improve NOHAs druglike properties, we demonstrate that O-substitution by (glycosylic) acetal formation greatly increased the chemical stability of the hydroxyguanidine moiety and provided a nontoxic group that could be easily bioactivated by glycosidases. A straightforward synthetic concept was devised and afforded a series of diversely substituted prodrugs by O-conjugation of the hydroxyguanidine moiety with different monosaccharides. Systematic exploration of their bioactivation profile revealed that glucose-based prodrugs were more efficiently bioactivated than their galactose counterparts. NOS-dependent cytosolic NO release was quantified by automated fluorescence microscopy in a cell-based assay with murine macrophages. Glucose-based prodrugs performed particularly well and delivered cellular NO levels comparable to 1, demonstrating proof-of-concept." @default.
• W2511601009 created "2016-09-16" @default.
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• W2511601009 date "2016-08-29" @default.
• W2511601009 modified "2023-09-23" @default.
• W2511601009 title "Design, Synthesis, and Bioactivation of <i>O</i>-Glycosylated Prodrugs of the Natural Nitric Oxide Precursor <i>N</i>^ω-Hydroxy-<scp>l</scp>-arginine" @default.
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• W2511601009 doi "https://doi.org/10.1021/acs.jmedchem.6b00810" @default.
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