The synthesis of a novel class of cyclometalated gold(III) complexes supported by benzoylpyridine, benzylpyridine, and (1,2)-(+)-1,2-diaminocyclohexane (DACH) ligands, along with their crystal structures, is reported. These compounds provide a new scaffold to investigate biological properties of gold(III) complexes. The six complexes were prepared and characterized, following reactions of (C,N) cyclometalated gold(III) scaffolds, [Au(C^N)Cl] with DACH, which yielded a new series of cyclometaled gold(III), -, of the type [Au(C^NH)(DACH)] and the nitrogen-substituted cyclometalated Au(III), -, of the type [Au(C^N)(DACH)]. Antiproliferative activity of these complexes in a panel of cancer cells showed promising results with IC in the micromolar range and selectivity over normal epithelial cells, MRC5. Whereas shows minimal interaction with superhelical DNA except at high gold concentrations of 500 μM, complex does not show interaction even at 1000 μM. The complexes display significant uptake in OVCAR8 cancer cells within 200-1200 pmol/million cells with the exception of complex . Differential cellular uptake was observed for the complexes; for example, while and display significant uptake, showed minimal uptake. The compounds proved to be stable under physiological conditions and were minimally affected by either glutathione or sodium ascorbate. Cell cycle studies reveal a G1 arrest induced by representative complexes. The results reveal that enhanced Au(III) stabilization promoted by combined cyclometalated and DACH ligands may offer ligand tuning insights for novel anticancer drug design.