Turning on the red phosphorescence of a [Ru(tpy)(bpy)(Cl)]Cl complex by amide substitution: self-aggregation, toxicity, and cellular localization of an emissive ruthenium-based amphiphile

B. Siewert; M. Langerman; Y. Hontani; J. T. M. Kennis; V. H. S. van Rixel; B. Limburg; M. A. Siegler; V. Talens Saez; R. E. Kieltyka; S. Bonnet

doi:10.1039/C7CC02989F

Turning on the red phosphorescence of a [Ru(tpy)(bpy)(Cl)]Cl complex by amide substitution: self-aggregation, toxicity, and cellular localization of an emissive ruthenium-based amphiphile†

B. Siewert,

^ab M. Langerman,^a Y. Hontani,^c J. T. M. Kennis,^c V. H. S. van Rixel,^a B. Limburg,^a M. A. Siegler,^d V. Talens Saez,^a R. E. Kieltyka

^a and S. Bonnet

*^a

Author affiliations

* Corresponding authors

^a Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 233CC Leiden, The Netherlands
E-mail: bonnet@chem.leidenuniv.nl

^b Institute of Pharmacy, Pharmacognosy, University of Innsbruck, CCB, Innrain 80-82, 6020 Innsbruck, Austria

^c Department of Physics and Astronomy, Vrije Universiteit, De Boelelaan 1081, 1081HV Amsterdam, The Netherlands

^d Small Molecule X-ray Facility, Department of Chemistry Johns Hopkins University, Baltimore, MD 21218, USA

Abstract

Coupling the notoriously non-emissive complex [Ru(tpy)(bpy)Cl]Cl (tpy = 2,2′:6′,2′′-terpyridine, bpy = 2,2′-bipyridine) to a C₁₂ alkyl chain via an amide linker on the 4′ position of the terpyridine yielded a new amphiphilic ruthenium complex showing red emission and chloride-dependent aggregation properties. This emissive complex is highly cytotoxic in A549 non-small lung cancer cells where it can be followed by confocal microscopy. Uptake occurs within minutes, first by insertion into the cellular membrane, and then by migration to the peri-nuclear region.

Chemical Communications

Turning on the red phosphorescence of a [Ru(tpy)(bpy)(Cl)]Cl complex by amide substitution: self-aggregation, toxicity, and cellular localization of an emissive ruthenium-based amphiphile†

Abstract

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Turning on the red phosphorescence of a [Ru(tpy)(bpy)(Cl)]Cl complex by amide substitution: self-aggregation, toxicity, and cellular localization of an emissive ruthenium-based amphiphile

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