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

Arindam Mukherjee, Shanta Dhar, Munirathinam Nethaji, Akhil R. Chakravarty

Research output: Contribution to journalArticle

59 Scopus citations

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 K app value of 4.1 × 105 M-1 and displays oxidative cleavage of supercoiled DNA in the presence of H2O 2 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.

Original languageEnglish (US)
Pages (from-to)349-353
Number of pages5
JournalDalton Transactions
Issue number2
DOIs
StatePublished - Jan 21 2005

    Fingerprint

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this