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

McCann M., McGinley J., Ni K., O'Connor M., Kavanagh K., McKee V., Colleran J., Devereux M., Gathergood N., Barron N., Prisecaru A. and Kellett A. 

Chemical Communications49, 2341-2343, 2013.

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.