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Cyanine‐ and Rhodamine‐Derived Alkynes for the Selective Targeting of Cancerous Mitochondria through Radical Thiol‐Yne Coupling in Live Cells.

Cyanine‐ and Rhodamine‐Derived Alkynes for the Selective Targeting of Cancerous Mitochondria through Radical Thiol‐Yne Coupling in Live Cells.

Authors :
Köckenberger, Johannes
Klemt, Insa
Sauer, Caroline
Arkhypov, Anton
Reshetnikov, Viktor
Mokhir, Andriy
Heinrich, Markus R.
Source :
Chemistry - A European Journal. 8/10/2023, Vol. 29 Issue 45, p1-12. 12p.
Publication Year :
2023

Abstract

Despite their long history and their synthetic potential underlined by various recent advances, radical thiol‐yne coupling reactions have so far only rarely been exploited for the functionalization of biomolecules, and no examples yet exist for their application in live cells ‐ although natural thiols show widespread occurrence therein. By taking advantage of the particular cellular conditions of mitochondria in cancer cells, we have demonstrated that radical thiol‐yne coupling represents a powerful reaction principle for the selective targeting of these organelles. Within our studies, fluorescently labeled reactive alkyne probes were investigated, for which the fluorescent moiety was chosen to enable both mitochondria accumulation as well as highly sensitive detection. After preliminary studies under cell‐free conditions, the most promising alkyne‐dye conjugates were evaluated in various cellular experiments comprising analysis by flow cytometry and microscopy. All in all, these results pave the way for improved future therapeutic strategies relying on live‐cell compatibility and selectivity among cellular compartments. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09476539
Volume :
29
Issue :
45
Database :
Academic Search Index
Journal :
Chemistry - A European Journal
Publication Type :
Academic Journal
Accession number :
169875215
Full Text :
https://doi.org/10.1002/chem.202301340