Synthesis and cellular uptake of neutral rhenium() morpholine complexes

Morpholine motifs have been used extensively as targeting moieties for lysosomes, primarily in fluorescence imaging agents. Traditionally these imaging agents are based on organic molecules which have several shortcomings including small Stokes shifts, short emission lifetimes, and susceptibility to...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2024-02, Vol.53 (7), p.347-3413
Main Authors: Bader, Christie A, Simpson, Peter V, Dallerba, Elena, Stagni, Stefano, Johnson, Ian R. D, Hickey, Shane M, Sorvina, Alexandra, Hackett, Mark, Sobolev, Alexandre N, Brooks, Doug A, Massi, Massimiliano, Plush, Sally E
Format: Article
Language:English
Subjects:
Emission
Endosomes
Fluorescence
Imaging
Low concentrations
Lysosomes
Morpholine
Organic chemistry
Phosphorescence
Rhenium
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Summary:Morpholine motifs have been used extensively as targeting moieties for lysosomes, primarily in fluorescence imaging agents. Traditionally these imaging agents are based on organic molecules which have several shortcomings including small Stokes shifts, short emission lifetimes, and susceptibility to photobleaching. To explore alternative lysosome targeting imaging agents we have used a rhenium based phosphorescent platform which has been previously demonstrated to have an improved Stokes shift, a long lifetime emission, and is highly photostable. Rhenium complexes containing morpholine substituted ligands were designed to accumulate in acidic compartments. Two of the three complexes prepared exhibited bright emission in cells, when incubated at low concentrations (20 μM) and were non-toxic at concentrations as high as 100 μM, making them suitable for live cell imaging. We show that the rhenium complexes are amenable to chemical modification and that the morpholine targeted derivatives can be used for live cell confocal fluorescence imaging of endosomes-lysosomes. Neutral Re(I) morpholine complexes exhibiting long emission lifetimes, high photo- and pH stability and low cytotoxicity for imaging endosome-lysosome compartments.
ISSN:1477-9226
1477-9234
DOI:10.1039/d3dt03067a