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Bioorthogonal Phosphorogenic Rhenium(I) Polypyridine Sydnone Complexes for Specific Lysosome Labeling.

Justin Shum¹, Pei-Zhi Zhang¹, Lawrence Cho-Cheung Lee¹

¹Department of Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong, P. R. China.

|March 25, 2020

Summary

Researchers developed novel rhenium(I) polypyridine complexes with sydnone moieties for bioorthogonal labeling. These probes exhibit enhanced phosphorescence upon reaction, enabling specific lysosomal labeling in live cells.

Keywords:

bioorthogonal reactions imaging agents phosphorogenic probes rhenium sydnones

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Area of Science:

Bioorthogonal chemistry
Coordination chemistry
Photophysics

Background:

Novel bioorthogonal reactions are crucial for chemical biology labeling.
Sydnone-based probes with phosphorescence turn-on have not been explored.
Rhenium(I) polypyridine complexes offer unique photophysical properties.

Purpose of the Study:

To synthesize and characterize rhenium(I) polypyridine complexes with sydnone moieties.
To investigate their potential as bioorthogonal phosphorogenic probes.
To evaluate their performance in biomolecule labeling and cellular imaging.

Main Methods:

Synthesis and characterization of rhenium(I) polypyridine complexes.
Photophysical studies including emission enhancement and lifetime measurements.
Bioorthogonal reactions, specifically strain-promoted sydnone-alkyne cycloaddition (SPSAC).
Conjugation with biomolecules (bovine serum albumin) and cellular imaging experiments.

Main Results:

The synthesized complexes showed significant emission enhancement (8.8-17.3) upon SPSAC with bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN-OH).
Conjugation with BCN-modified bovine serum albumin (BCN-BSA) resulted in higher emission enhancement (up to 38.9) and extended lifetimes (1.80-4.71 μs).
One complex successfully labeled lysosomes in live cells with high specificity (Pearson's coefficient of 0.83) when ligated with a morpholine derivative.

Conclusions:

Novel rhenium(I) polypyridine complexes incorporating sydnone moieties function as effective bioorthogonal phosphorogenic probes.
These probes demonstrate significant signal enhancement and specific cellular labeling capabilities.
The developed probes show promise for advanced bioimaging applications in live cells.