Publication

Regulating the anticancer properties of organometallic dendrimers using pyridylferrocene entities: synthesis, cytotoxicity and DNA binding studies

Paul Joseph Dyson, Tina Riedel
2016
Journal Articles

Abstract

A new series of eight first- and second-generation heterometallic ferrocenyl-derived metal-arene metallodendrimers, containing ruthenium(II) p-cymene, ruthenium(II)-hexamethylbenzene, rhodium(III)-cyclopentadienyl or iridium(III)-cyclopentadienyl moieties have been prepared. The metallodendrimers were synthesized by first reacting DAB-(NH2)(n), (where n = 4 or 8, DAB = diaminobutane) with salicylaldehyde, and then the Schiff-base dendritic ligands were reacted in a one-pot reaction with the appropriate (eta(6)-p-iPrC(6)H(4)Me)RuCl2, (eta(6)-C6Me6)RuCl2, (eta(5)-C5Me5)IrCl2 or (eta(5)-C5Me5)RhCl2 dimers, in the presence of 4-pyridylferrocene. Heterometallic binuclear analogues were prepared as models of the larger metallodendrimers. All complexes have been characterized using analytical and spectroscopic methods. The cytotoxicity of the heterometallic metallodendrimers and their binuclear analogues were evaluated against A2780 cisplatin-sensitive and A2780cisR cisplatin-resistant human ovarian cancer cell lines and against a non-tumorigenic HEK-293 human embryonic kidney cell tine. The second generation Ru(II)-eta(6)-C6Me6 metallodendrimer is the most cytotoxic and selective compound. DNA binding experiments reveal that a possible mode-of-action of these compounds involves non-covalent interactions with DNA.

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https://infoscience.epfl.ch/entities/publication/055ececa-490f-40c2-8eee-d1ce68c372e7

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Paul Joseph Dyson, Tina Riedel
2016
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/055ececa-490f-40c2-8eee-d1ce68c372e7

About this result

Related concepts (9)

Coordinate covalent bond

In coordination chemistry, a coordinate covalent bond, also known as a dative bond, dipolar bond, or coordinate bond is a kind of two-center, two-electron covalent bond in which the two electrons derive from the same atom. The bonding of metal ions to ligands involves this kind of interaction. This type of interaction is central to Lewis acid–base theory. Coordinate bonds are commonly found in coordination compounds. Coordinate covalent bonding is ubiquitous.

Covalent bond

A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms, when they share electrons, is known as covalent bonding. For many molecules, the sharing of electrons allows each atom to attain the equivalent of a full valence shell, corresponding to a stable electronic configuration. In organic chemistry, covalent bonding is much more common than ionic bonding.

Non-covalent interaction

In chemistry, a non-covalent interaction differs from a covalent bond in that it does not involve the sharing of electrons, but rather involves more dispersed variations of electromagnetic interactions between molecules or within a molecule. The chemical energy released in the formation of non-covalent interactions is typically on the order of 1–5 kcal/mol (1000–5000 calories per 6.02 molecules). Non-covalent interactions can be classified into different categories, such as electrostatic, π-effects, van der Waals forces, and hydrophobic effects.

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