Series of transition metal complexes [Fe (HL) 2 Cl(H 2 O)](1), [Co (HL) 2 ](2), [Ni (HL) 2 ](3) and [Cu (HL) 2 ](4) were derived on condensation of Schiff base ligand o-hydroxyacetophenone with 2-fluoroaniline in 1:1 ratio (HL) and characterized by spectral and analytical techniques. Based on the studies, complex 1 was found to be octahedral and complexes (2), ( 3) and ( 4) square planar. Coats-Redfern calculations suggest that all the complexes are nonspontaneous and thermally stable. DNA binding studies revealed intercalation binding mode, while intrinsic binding constant (K b ) and Stern-Volmer quenching constant (K sq ) support high binding abilities. The nuclease activity using CT-DNA was studied by gel electrophoresis. Docking studies were deduced using Accelry's Discovery Studio 2.1 program to understand binding affinities.The MD simulation, carried in order to analyse the stability of ligand and human topoisomerase I (PDB ID: 1T8I) complex for 100 ns using the Desmond 2020.1 from Schrödinger, LLC, revealed stable conformation of the ligand. In vivo, carrageenan induced inflammation studies in paw volume were carried out in rats, and results showed a higher rate of oedema inhibition for complex 4. Cytotoxicity and antimicrobial assay reveal that complex 4 exhibited higher cytotoxic and antimicrobial activity over other complexes and the ligand.