This paper encompasses the synthesis, structural characterization, and evaluation of supercoiled pBR322 plasmid DNA-cleavage and DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging properties of newly synthesized tetra-substituted Co-II (5), Cu-II (6), Zn-II (7) and Mg-II (8) phthalocyanines bearing 4-methyl-N-(4-morpholinophenyl)benzenesulfonamide units at non-peripheral sites of phthalocyanine skeleton. The structural characterization of these new metallated phthalocyanines were performed via UV-vis, elemental analysis, FT-IR (ATR sampling accessory), H-1-NMR and C-13-NMR spectroscopic techniques (for 7 and 8) and MALDI-TOF mass spectral data. The new compounds (5-8) exhibited good solubility in common organic solvents, and as well as no sort of aggregation was perceived at studied concentrations and solvents. Compound 7 indicated oxidative photocleavage activities in the presence of H2O2, indicating the conversion of supercoiled pBR322 plasmid DNA to nicked circular form (19.90%) and linear form (4.40%). Compound 5 displayed the highest radical scavenging activities among the tested compounds. The DPPH-radical scavenging percentages of 5 ranged from 85.35 +/- 2.45% (12.5 mu M) to 95.38 +/- 1.44% (100 mu M). These compounds are favorable for further research, owing to a broad range of biological and pharmaceutical activities of morpholine scaffold.