Chemical Communications 2013-03-21

A new phenanthroline-oxazine ligand: synthesis, coordination chemistry and atypical DNA binding interaction.

Malachy McCann, John McGinley, Kaijie Ni, Mark O'Connor, Kevin Kavanagh, Vickie McKee, John Colleran, Michael Devereux, Nicholas Gathergood, Niall Barron, Andreea Prisecaru, Andrew Kellett

Index: Chem. Commun. (Camb.) 49(23) , 2341-3, (2013)

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Abstract

1,10-Phenanthroline-5,6-dione and l-tyrosine methyl ester react to form phenanthroline-oxazine (PDT) from which [Cu(PDT)(2)](ClO(4))(2) and [Ag(PDT)(2)]ClO(4)·2MeOH are obtained. Binding to calf-thymus DNA by Ag(I) and Cu(II) PDT complexes exceed bis-1,10-phenanthroline analogues and the minor groove binding drugs, pentamidine and netropsin. Furthermore, unlike the artificial metallonuclease, [Cu(phen)(2)](2+), the [Cu(PDT)(2)](2+) complex does not cleave DNA in the presence of added reductant indicating unique interaction with DNA.