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

doi:10.1039/C3CC38710K

A new phenanthroline–oxazine ligand: synthesis, coordination chemistry and atypical DNA binding interaction†

Malachy McCann,*^a John McGinley,^a Kaijie Ni,^a Mark O'Connor,^a Kevin Kavanagh,^b Vickie McKee,^c John Colleran,^d Michael Devereux,^d Nicholas Gathergood,^e Niall Barron,^e Andreea Prisecaru^e and Andrew Kellett*^e

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* Corresponding authors

^a Department of Chemistry, National University of Ireland Maynooth, Maynooth, Co. Kildare, Ireland
E-mail: mmcann@nuim.ie
Tel: +353 1 7083767

^b Department of Biology, National University of Ireland Maynooth, Maynooth, Co. Kildare, Ireland

^c Chemistry Department, Loughborough University, Loughborough, Leics, UK

^d The Inorganic Pharmaceutical and Biomimetic Research Centre, Focas Research Institute, Dublin Institute of Technology, Camden Row, Dublin 8, Ireland

^e School of Chemical Sciences and National Institute of Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland
E-mail: andrew.kellett@gmail.com
Tel: +353 1 7005461

Abstract

1,10-Phenanthroline-5,6-dione and L-tyrosine methyl ester react to form phenanthroline–oxazine (PDT) from which [Cu(PDT)₂](ClO₄)₂ and [Ag(PDT)₂]ClO₄·2MeOH 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.

Chemical Communications

A new phenanthroline–oxazine ligand: synthesis, coordination chemistry and atypical DNA binding interaction†

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

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