The complexes [Cu(salH) 2(H 2O)] (1), [Cu(dipsH) 2(H 2O)] (2), {Cu(3-MeOsal)(H 2O) 0.75} n (3), [Cu(dipsH) 2(BZDH) 2] (4), [Cu(dipsH) 2(2-MeOHBZDH) 2]•EtOH (5), [Cu(sal)(phen)] (6), [Cu(dips)(phen)]•H 2O (7), and [Cu(3-MeOsal)(phen)] •H 2O (8) (salH 2 = salicylic acid; dipsH 2 = 3,5-diisopropylsalicylic acid; 3-MeOsalH 2 = 3-methoxysalicylic acid; BZDH = benzimidazole; 2-MeOHBZDH = 2 methanolbenzimidazole and phen =1,10-phenanthroline) were prepared and characterized. Structures of 4, 5, and 8 were determined by X-ray crystallography. Compounds 1-8 are potent superoxide dismutase mimetics, and they are inactive as inhibitors of COX-2 activity. Compounds 1, 4, and 5 exhibit moderate inhibition of COX-1. Complexes 6-8 display rapid micromolar cytotoxicity against cisplatin sensitive (breast (MCF-7), prostate (DU145), and colon (HT29)) and cisplatin resistant (ovarian (SK-OV-3)) cell lines compared to 1-5, and they exhibit potent in vitro DNA binding and cleavage capabilities. © 2012 American Chemical Society.