Publication

Is the aromatic fragment of piano-stool ruthenium compounds an essential feature for anticancer activity? The development of new Ru-II-[9]aneS(3) analogues

Paul Joseph Dyson, Claudine Scolaro
2005
Journal Articles

Abstract

New half-sandwich R-II-[9]aneS(3) complexes ([9]aneS(3) = 1,4,7-trithiacyclononane), namely [RuCl2(PTA)([9]aneS(3))] (4), [RuCl(PTA)(2)([9]aneS(3))][OTf] (5), [RuCl(en)([9]aneS(3))][OTf] (6), [RuCl(enac)([9]aneS(3))][OTf] (7), [RuCl(bipy)([9]ane-S-3)][OTf] (8), and [Ru(dmso-S)(bipy)([9]aneS(3))]OTf (9) [PTA = 1,3,5-triaza-7-phosphaadamantane; enac = 1,2-bis-(isopropyleneimino)ethane; OTf = CF3SO3-] were prepared from Ru-[9]aneS(3)-dmso precursors and structurally characterized, both in solution and in the solid state by X-ray crystallography. Some of them are analogs of known cytotoxic organometallic Ru-II-(eta(6)-arene) and Ru-II-(eta(5)-cyclopentadienyl) compounds, in which the aromatic fragment is replaced by the sulfur macrocycle 1,4,7-trithiacyclononane, while the rest of the coordination sphere is left unchanged. Similarly to the aromatic analogs for which data are available, in aqueous solution the Ru-[9]aneS(3) complexes (with the exception of 5) hydrolyze a chloride (or a dmso in the case of 9) to give the corresponding aquo species. This process is rapidly reversed in the presence of free chloride, and coordination of phosphate is likely to occur to the aquo species in phosphate buffered solutions at physiological pH. Preliminary in vitro tests performed on complexes 4-6 against the mouse adenocarcinoma cancer cell line (TS/A) and the human mammary normal cell line (HBL-100) showed that, in general, the Ru-[9]aneS(3) compounds have a cytotoxicity comparable to that of the corresponding organometallic analogs. These results suggest that the aromatic fragment of the piano-stool Ru-II compounds is not an essential feature for the in vitro anticancer activity, and it might be effectively replaced by another face-capping ligand with a low steric demand, such as [9]aneS(3). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Paul Joseph Dyson, Claudine Scolaro
2005
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/b3c77e34-0e14-4087-baab-de91ed117fc0

About this result

Related concepts (32)

Coordination complex

A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the coordination centre, and a surrounding array of bound molecules or ions, that are in turn known as ligands or complexing agents. Many metal-containing compounds, especially those that include transition metals (elements like titanium that belong to the periodic table's d-block), are coordination complexes. Coordination complexes are so pervasive that their structures and reactions are described in many ways, sometimes confusingly.

Coordination sphere

In coordination chemistry, the first coordination sphere refers to the array of molecules and ions (the ligands) directly attached to the central metal atom. The second coordination sphere consists of molecules and ions that attached in various ways to the first coordination sphere. The first coordination sphere refers to the molecules that are attached directly to the metal. The interactions between the first and second coordination spheres usually involve hydrogen-bonding. For charged complexes, ion pairing is important.

Coordination number

In chemistry, crystallography, and materials science, the coordination number, also called ligancy, of a central atom in a molecule or crystal is the number of atoms, molecules or ions bonded to it. The ion/molecule/atom surrounding the central ion/molecule/atom is called a ligand. This number is determined somewhat differently for molecules than for crystals. For molecules and polyatomic ions the coordination number of an atom is determined by simply counting the other atoms to which it is bonded (by either single or multiple bonds).

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