N, N-diarylazodioxides, the dimers of nitrosoarenes such as nitrosobenzene, can act as chelating ligands for both main-group and transition metals. However, complexes of this ligand class remain rare, with only five thus far structurally characterized in the literature (including two by the Boyd research group). Previous work by our research group on the cobalt(II) complex salts [Co(bpy)(az)2](PF6)2] and [Co(az)4](PF6)2], where az = cis-N, N-diphenylazodioxide and bpy = 2,2'-bipyridyl, involved the screening of both species as possible anticancer agents against the SK-HEP-1 human liver cancer cell line. Both compounds induced substantial apoptosis as an increasing function of concentration and time. Measurements of apoptosis-related proteins indicated that both the extrinsic and intrinsic pathways of apoptosis were activated. The apoptotic activity induced by these azodioxide complexes was not displayed by the salt CoCl2, the simpler complexes Co(phen)Cl2 and Co(bpy)Cl2, or by the free molecule nitrosobenzene (PhNO), the monomeric form of the azodioxide ligand. This research describes the synthesis, structural characterization, and biological evaluation of an additional ten N, N-diphenylazodioxide complexes of the first-series transition metals manganese, nickel, copper, and zinc. The N, N-diphenylazodioxide ligand is shown to be present in both mono- and bimetallic complexes with various coordination geometries.

Synthesis and biological evaluation of azodioxide compounds of first-series transition metals

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