π-Stacking between Casiopeinas® and DNA bases

Abstract

Casiopeínas® are copper complexes with the general formula [Cu(N–N)(N–O)]NO₃ and [Cu(N–N)(O–O)]NO₃ where N–N denotes a substituted bipyridine or phenanthroline, N–O indicates α-aminoacidate or peptide and O–O represents acetylacetonate or salicylaldehyde. This family of compounds has been evaluated in vitro and in vivo showing cytotoxic, genotoxic, and antineoplastic activity. The action mechanism is still not completely elucidated, but the possibility exists that these compounds interact with DNA by intercalation due to the aromatic moiety. In this work we found, using the properties of the electron density of a π-complex model base–Casiopeína®–base, that the stacking mechanism between Casiopeínas® and DNA bases is due to an electron density deficiency of the ligand of the Casiopeína® which is compensated for by an electron transfer from adenines by a π–π interaction.