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Issue 2, 2005
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Ternary iron(ii) complex with an emissive imidazopyridine arm from Schiff base cyclizations and its oxidative DNA cleavage activity

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Abstract

The ternary iron(II) complex [Fe(L′)(L″)](PF6)3 (1) as a synthetic model for the bleomycins, where L′ and L″ are formed from metal-mediated cyclizations of N,N′-(2-hydroxypropane-1,3-diyl)bis(pyridine-2-aldimine) (L), is synthesized and structurally characterized by X-ray crystallography. In the six-coordinate iron(II) complex, ligands L′ and L″ show tetradentate and bidentate chelating modes of bonding. Ligand L′ is formed from an intramolecular attack of the alcoholic OH group of L to one imine moiety leading to the formation of a stereochemically constrained five-membered ring. Ligand L″ which is formed from an intermolecular reaction involving one imine moiety of L and pyridine-2-carbaldehyde has an emissive cationic imidazopyridine pendant arm. The complex binds to double-stranded DNA in the minor groove giving a Kapp value of 4.1 × 105 M−1 and displays oxidative cleavage of supercoiled DNA in the presence of H2O2 following a hydroxyl radical pathway. The complex also shows photo-induced DNA cleavage activity on UV light exposure involving formation of singlet oxygen as the reactive species.

Graphical abstract: Ternary iron(ii) complex with an emissive imidazopyridine arm from Schiff base cyclizations and its oxidative DNA cleavage activity

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Supplementary files

Article information


Submitted
01 Oct 2004
Accepted
19 Nov 2004
First published
06 Dec 2004

Dalton Trans., 2005, 349-353
Article type
Paper

Ternary iron(II) complex with an emissive imidazopyridine arm from Schiff base cyclizations and its oxidative DNA cleavage activity

A. Mukherjee, S. Dhar, M. Nethaji and A. R. Chakravarty, Dalton Trans., 2005, 349
DOI: 10.1039/B415864D

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