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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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Publication details

The article was received on 01 Oct 2004, accepted on 19 Nov 2004 and first published on 06 Dec 2004


Article type: Paper
DOI: 10.1039/B415864D
Citation: Dalton Trans., 2005, 349-353
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    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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