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Issue 9, 2012
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Ruthenium(ii) arene complexes with chelating chloroquine analogue ligands: Synthesis, characterization and in vitroantimalarial activity

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Abstract

Three new ruthenium complexes with bidentate chloroquine analogue ligands, [Ru(η6-cym)(L1)Cl]Cl (1, cym = p-cymene, L1 = N-(2-((pyridin-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine), [Ru(η6-cym)(L2)Cl]Cl (2, L2 = N-(2-((1-methyl-1H-imidazol-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine) and [Ru(η6-cym)(L3)Cl] (3, L3 = N-(2-((2-hydroxyphenyl)methylimino)ethyl)-7-chloroquinolin-4-amine) have been synthesized and characterized. In addition, the X-ray crystal structure of 2 is reported. The antimalarial activity of complexes 1–3 and ligands L1, L2 and L3, as well as the compound N-(2-(bis((pyridin-2-yl)methyl)amino)ethyl)-7-chloroquinolin-4-amine (L4), against chloroquine sensitive and chloroquine resistant Plasmodium falciparum malaria strains was evaluated. While 1 and 2 are less active than the corresponding ligands, 3 exhibits high antimalarial activity. The chloroquine analogue L2 also shows good activity against both the chloroquine sensitive and the chloroquine resistant strains. Heme aggregation inhibition activity (HAIA) at an aqueous buffer/n-octanol interface (HAIR50) and lipophilicity (D, as measured by water/n-octanol distribution coefficients) have been measured for all ligands and metal complexes. A direct correlation between the D and HAIR50 properties cannot be made because of the relative structural diversity of the complexes, but it may be noted that these properties are enhanced upon complexation of the inactive ligand L3 to ruthenium, to give a metal complex (3) with promising antimalarial activity.

Graphical abstract: Ruthenium(ii) arene complexes with chelating chloroquine analogue ligands: Synthesis, characterization and in vitroantimalarial activity

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Supplementary files

Article information


Submitted
02 Nov 2011
Accepted
05 Dec 2011
First published
17 Jan 2012

Dalton Trans., 2012,41, 2764-2773
Article type
Paper

Ruthenium(II) arene complexes with chelating chloroquine analogue ligands: Synthesis, characterization and in vitroantimalarial activity

L. Glans, A. Ehnbom, C. de Kock, A. Martínez, J. Estrada, P. J. Smith, M. Haukka, R. A. Sánchez-Delgado and E. Nordlander, Dalton Trans., 2012, 41, 2764
DOI: 10.1039/C2DT12083F

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