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In search of new chemical nucleases, the synthesis of dehydroacetic acid based hydrazone Schiff’s base and its colored complexes with transition metal Co(II), Ni(II), Cu(II), Mn(II) and Zn(II) has been achieved. All synthesized compounds were screened for their DNA photocleavage potential using the plasmid DNA via gel electrophoresis method. Synthesized compounds were also screened for antibacterial activity against gram (+) and gram (-) bacteria using Oxacillin as a reference standard. It has been found that activity increases significantly upon coordination. The hydrazone Schiff’s base utilized in present study has been synthesized by a condensation reaction between 2-methylmalonohydrzide and dehydroacetic acid. Further, this novel ligand was allowed to react with different transition metal salts in 1:1 ratio to synthesize transition metal complexes. All the compounds were characterized on the basis of various spectroscopic techniques like UV-Visible, 1H, 13C-NMR, elemental analysis, FTIR spectroscopy and mass spectrometry. 1H NMR data of complexes showed the coordination of -OH atom with subsequent loss of proton and FTIR spectral data revealed the participation of enolic oxygen atom of ligand in coordination with metal ion. UV-Visible data suggested square planner geometry of the synthesized metal complexes.