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Molecules 2014, 19(5), 6031-6046; doi:10.3390/molecules19056031
Article

Exploiting Natural Products to Build Metalla-Assemblies: The Anticancer Activity of Embelin-Derived Rh(III) and Ir(III) Metalla-Rectangles

1
,
2
,
1
,
2
 and
1,*
1 Institute of Chemistry, University of Neuchatel, Avenue de Bellevaux 51, CH-2000 Neuchatel, Switzerland 2 CSIR-Centre for Cellular and Molecular Biology, Uppal Road, Habsiguda, Hyderabad-500 007, India
* Author to whom correspondence should be addressed.
Received: 23 April 2014 / Revised: 6 May 2014 / Accepted: 7 May 2014 / Published: 12 May 2014
(This article belongs to the Special Issue Practical Applications of Metal Complexes)
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Abstract

Six new pentamethylcyclopentadienyl Rh(III) and Ir(III) metalla-rectangles ([3](CF3SO3)4–[8](CF3SO3)4) have been prepared by a self-assembly strategy using the embelin-derived metalla-clips (η5-C5Me5)2M24-C6HRO4O)Cl2 (M = Rh, 1; M = Ir, 2; R = (CH2)10CH3) and the linear ditopic ligands, pyrazine, 4,4'-bipyridine and 1,2-bis (4-pyridyl)ethylene. These new metalla-rectangles have been obtained in high yield and isolated as their triflate salts. The complexes have been fully characterized by standard spectroscopic techniques and the antiproliferative activity of these tetranuclear complexes was evaluated in vitro on cancerous (DU-145, A-549, HeLa) and noncancerous (HEK-293) cell lines. The biological study has showed a better activity for the rhodium derivatives over the iridium analogs and for all complexes a very good selectivity for cancerous over noncancerous cells. The presence of lipophilic side chains coupled with the positive charge of the tetranuclear complexes suggested a cytotoxic activity involving the mitochondrial machinery, as demonstrated by multiple biological experiments.
Keywords: bioinorganic chemistry; metalla-assemblies; coordination-driven self-assembly; anticancer activity; half-sandwich complexes bioinorganic chemistry; metalla-assemblies; coordination-driven self-assembly; anticancer activity; half-sandwich complexes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Gupta, G.; Kumar, J.M.; Garci, A.; Nagesh, N.; Therrien, B. Exploiting Natural Products to Build Metalla-Assemblies: The Anticancer Activity of Embelin-Derived Rh(III) and Ir(III) Metalla-Rectangles. Molecules 2014, 19, 6031-6046.

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