A new azacrown bis-macrocycle (5) and its mono–cyclic analogue (7) were synthesized and characterized by FT-IR, 1H NMR, 13C NMR, DEPT 13C NMR, MS, and elemental analysis. The reaction with copper(II) nitrate yielded the corresponding complexes, formulated as Cu(5)(NO3)2·3H2O (8), and Cu(7)(NO3)2·2.5H2O (9). Also the stoichiometries of the complexes were determined in alcoholic solution and the results show that for both complexes the ratio of ligand to metal was 1:1 in methanol. The redox behavior of both complexes has been studied by cyclic voltammetry in DMF. Cyclic voltamogram of 8 shows quasi-reversible CuII/CuI redox couple whereas 9 shows a reversible CuII/CuI redox couple. Mono- and bis-macrocycle copper(II) complexes (8 and 9 respectively) cleaved plasmid pGS2 DNA by using an oxidative mechanism with 3- mercaptopropionic acid (MPA) as the reductant under aerobic conditions. The bis-macrocycle copper(II) complex 8 showed higher cleavage efficiency than their mono-macrocycle analogue 9 at the same Cu2+ concentration.