Structural Control of Cell Permeability with Highly Emissive Europium(III) Complexes Permits Different Microscopy Applications

Four anionic europium complexes are described based on triazacyclononane tris-carboxylate or phosphinate ligands. In each case, the three sensitising chromophores comprise a substituted aryl-alkynyl pyridine group, with complex brightness in water falling in the range 4 to 23 mM^-1 cm^-1. para-Substitution of the aryl ring with carboxymethyl groups gives complexes that are taken into cells, stain the lysosomes selectively and unexpectedly permit lifetime measurements of lysosomal pH. In contrast, the introduction of sulfonate groups inhibits cell uptake enabling the Eu complex to be used as an extracellular donor for FRET applications at the membrane surface. Using time-gated FRET microscopy, the cell membrane structure was highlighted, in which Cell Mask Deep Red was used as a membrane- localized FRET acceptor.