Tuning The Intracellular Distribution of [3+2+1] Iridium(III) Complexes In Bacterial And Mammalian Cells By iClick Reaction With Biomolecular Carriers Functionalized With Alkynone Groups

Mueller, Victoria V. L. and Moreth, Dominik and Kowalski, Konrad and Kowalczyk, Aleksandra and Gapinska, Magdalena and Kutta, Roger Jan and Nuernberger, Patrick and Schatzschneider, Ulrich (2024) Tuning The Intracellular Distribution of [3+2+1] Iridium(III) Complexes In Bacterial And Mammalian Cells By iClick Reaction With Biomolecular Carriers Functionalized With Alkynone Groups. CHEMISTRY-A EUROPEAN JOURNAL, 30 (56): e202401603. ISSN 0947-6539, 1521-3765

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Abstract

Three iridium(III) triazolato complexes of the general formula [Ir(triazolato(R,R'))(ppy)(terpy)]PF6 with ppy=2-phenylpyridine and terpy=2,2':6',2''-terpyridine were efficiently prepared by iClick reaction of [Ir(N-3)(ppy)(terpy)]PF6, with alkynes and alkynones, which allowed facile introduction of biological carriers such as biotin and cholic acid. In contrast to the precursor azido complex, which decomposed upon photoexcitation on a very short time scale, the triazolato complexes were stable in solution for up to 48 h. They emit in the spectral region around 540 nm with a quantum yield of 15-35 % in aerated acetonitrile solution and exhibit low cytotoxicity with IC50 values >50 mu M for most complexes in L929 and HeLa cells, demonstrating their high suitability as luminescent probes. Cell uptake studies with confocal luminescence microscopy in prokaryotic Gram-positive S. aureus and Gram-negative E. coli bacteria as well as eukaryotic mammalian L929 and HeLa cells showed significant uptake in particular of the cholic acid conjugates iridium(III) moiety and distinct intracellular distribution modulated by the nature of the peripheral functional groups that can easily be modified by the iClick reaction.

Item Type: Article
Uncontrolled Keywords: ELECTRON-POOR ALKYNES; CYCLOMETALATED IRIDIUM(III); PROTEIN-BINDING; AZIDE; CYCLOADDITION; PALLADIUM(II); LUMINESCENCE; RHODIUM(III); PLATINUM(II); TRACKING
Subjects: 500 Science > 540 Chemistry & allied sciences
500 Science > 570 Life sciences
Divisions: Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Physical Chemistry I > Prof. Dr. Patrick Nürnberger
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Jan 2026 06:02
Last Modified: 14 Jan 2026 06:02
URI: https://pred.uni-regensburg.de/id/eprint/65055

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