Issue 23, 2013
From the journal:

Chemical Communications

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 Prisecarue  and  Andrew Kellett*e  

* 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.

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

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Article information

DOI
https://doi.org/10.1039/C3CC38710K
Article type
Communication
Submitted
04 Dec 2012
Accepted
05 Feb 2013
First published
06 Feb 2013

Chem. Commun., 2013,49, 2341-2343

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

M. McCann, J. McGinley, K. Ni, M. O'Connor, K. Kavanagh, V. McKee, J. Colleran, M. Devereux, N. Gathergood, N. Barron, A. Prisecaru and A. Kellett, Chem. Commun., 2013, 49, 2341 DOI: 10.1039/C3CC38710K

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