2,7-Difluoroaminopyronins are a novel set of fluorescent compounds which have the ability to rapidly form covalent bonds with amines via unique SNAr reaction. In this SNAr reaction, the aminopyronin fluorophore can be attacked by a free amino residue at the 9 position resulting in the substitution of the existing amino group. Previous studies on these compounds have shown that they can be used to selectively track favorable protein-protein interactions, via transfer from lysine residues. In this project, we have synthesized and determined the physical and photophysical properties of a small library of seven 2,7-difluoroaminopyronins analogs and have tested these analogs on bacterial and eurkaryotic cellular culture. We have found that two of the analogs readily pass through cell membranes and accumulate in a variety of cellular cultures (HeLa, Fiberblast, E.coli, and B.subtillis) at low toxicities, thus producing highly fluorescent cell lines for up to twelve days after a single fifteen minute incubation period. It is likely that these analogs, once diffused through the cell membrane, react with the amino groups of lysine residues of numerous proteins within cells thereby preventing the fluorophore molecules from escaping the cells. Fluorophore concentrations can then build up within the cell at low toxicities and persists through multiple cell division cycles.

Synthesis of aminopyonin analogs and their biological use

255th National Meeting (2018)

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