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
2013 Chemical Communications  
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 Á2MeOH 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
more » ... icating unique interaction with DNA. Scheme 1 Proposed reaction mechanism of phendio with L-tyrosine methyl ester leading to the formation of PDT.
doi:10.1039/c3cc38710k pmid:23407675 fatcat:eiakzy4tfnhfdehq6zroh37rla