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Issue 24, 2012
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Cellular delivery of pyrenyl-arene ruthenium complexes by a water-soluble arene ruthenium metalla-cage

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Abstract

Three pyrenyl-arene ruthenium complexes (M111–M333) of the general formula [Ru(η6-arene-pyrenyl)Cl2(pta)] (pta = 1,3,5-triaza-7-phosphaadamantane) have been synthesised and characterised. Prior to the coordination to ruthenium, pyrene was connected to the arene ligand via an alkane chain containing different functional groups: ester (L11), ether (L22) and amide (L33), respectively. Furthermore, the pyrenyl moieties of the Mnnn complexes were encapsulated within the hydrophobic cavity of the water soluble metalla-cage, [Ru66-p-cymene)6(tpt)2(donq)3]6+ (tpt = 2,4,6-tri-(pyridin-4-yl)-1,3,5-triazine; donq = 5,8-dioxydo-1,4-naphthoquinonato), while the arene ruthenium end was pointing out of the cage, thus giving rise to the corresponding host–guest systems [Mnnn⊂Ru66-p-cymene)6(tpt)2(donq)3]6+ ([Mnnn⊂cage]6+). The antitumor activity of the pyrenyl-arene ruthenium complexes (Mnnn) and the corresponding host–guest systems [Mnnn⊂cage][CF3SO3]6 were evaluated in vitro in different types of human cancer cell lines (A549, A2780, A2780cisR, Me300 and HeLa). Complex M22, which contains an ether group within the alkane chain, demonstrated at least a 10 times higher cytotoxicity than the reference compound [Ru(η6-p-cymene)Cl2(pta)] (RAPTA-C). All host–guest systems [Mnnn⊂cage]6+ showed good anticancer activity with IC50 values ranging from 2 to 8 μM after 72 h exposure. The fluorescence of the pyrenyl moiety allowed the monitoring of the cellular uptake and revealed an increase of uptake by a factor two of the M22 complex when encapsulated in the metalla-cage [Ru66-p-cymene)6(tpt)2(donq)3]6+.

Graphical abstract: Cellular delivery of pyrenyl-arene ruthenium complexes by a water-soluble arene ruthenium metalla-cage

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Article information


Submitted
26 Jan 2012
Accepted
20 Mar 2012
First published
22 Mar 2012

Dalton Trans., 2012,41, 7201-7211
Article type
Paper

Cellular delivery of pyrenyl-arene ruthenium complexes by a water-soluble arene ruthenium metalla-cage

M. A. Furrer, F. Schmitt, M. Wiederkehr, L. Juillerat-Jeanneret and B. Therrien, Dalton Trans., 2012, 41, 7201
DOI: 10.1039/C2DT30193H

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