Cellular uptake of small molecules and their linker-extended derivatives is defined by their chemical properties including lipophilicity and molecular weight. Simple modifications by fatty acids have been used to improve cellular uptake; however, it remains poorly understood whether such conjugates deliver the in-cell biological activity. We introduce conjugation with bile acids, relying on deoxycholic acid as a class representative, to enhance the cell permeability of linker-extended probes. When compared to more traditional chemical modification strategies (incl. palmitoylation, stearylation, biotinylation), these molecular systems show increased potency of bringing about the anticipated phenotypic effects at concentrations similar to those of the parent compounds.

Bile acid conjugation as a tool for enhancing intracellular delivery of biofunctional linker-extended constructs

256th National Meeting (2018)

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