As cancer remains the second leading cause of death in the United States, investigations into new cancer treatments are at the forefront of research efforts. The chemotherapeutic cisplatin has remained one of the most effective anticancer drugs; however, it has numerous toxic side effects, and its overuse has resulted in cisplatin resistant tumors. Chemotherapeutics with differing mechanisms of action may help to combat resistance and may be less toxic to healthy cells. The work presented here is focused on the synthesis and characterization of a series of Schiff-base containing copper compounds and assessment of these complexes for their anticancer properties. All compounds were characterized via single X-ray crystallography, infrared spectroscopy, UV-visible spectroscopy, and elemental analysis. Preliminary investigations into the biological activity of these new complexes included DNA cleavage studies and cancer cell proliferation assays in the presence and absence of complexes. In particular, complex-induced supercoiled (SC) DNA cleavage was observed in vitro, as demonstrated by an increase in both single (SN) and double nicked (DN) DNA with increasing complex concentration, indicating nuclease activity. Complex 2 had the greatest nuclease ability, cleaving all SC DNA at concentrations as low as 70 µM. Complex 1 had the second most cleavage followed by complex 3. To understand the mechanism of cleavage, ROS scavengers were introduced in similar experiments. It was determined that all three complexes cleave DNA using reactive oxygen species, more specifically O2-. The use of 1O2 was also prominent in the cleavage of DNA. The toxicity of the complexes was also tested against cancer cell lines and IC50 values were determined and compared to cisplatin. Cisplatin had an IC50 value of 26.3 µM, which was similar to complexes 3 and 1 at 22.8 µM and 30.1 µM respectively. Complex 2 had the highest IC50 value of 40.5 µM which was interesting because it had the highest nuclease ability. Ongoing studies are focused on further understanding the mechanism of action of these complexes to assess the potential application of these complexes as new chemotherapeutics. Additionally, testing these complexes against different cell lines such as prostate cancer, breast cancer, and healthy cell lines to understand if the complexes show any level of specificity.