Department of Chemistry, S. N. Vanitha Mahavidyalaya, Hyderabad-500 001, Telangana, India Department of Chemistry, Womens College, Osmania University, Hyderabad-500 095, Telangana, India Department of Chemistry, Nizam College, Osmania University, Hyderabad-500 001, Telangana, India Department of Chemistry, Osmania University, Hyderabad-500 007, Telangana, India E-mail : dr_saraladevich@yahoo.com Manuscript received online 28 August 2016, accepted 01 October 2016 In an attempt to understand the properties of compounds with potent anti-tumor and metal chelator properties, the structural aspects of (E)-N1 -[(3-hydroxy-5-(hydroxyl methyl)-2-methyl pyridine 4-yl)methylene]aceto hydrazone hydrochloride (HHMMPMAH) were studied by various spectral techniques. To understand chelation properties of the same compound, its CuII complex was synthesized and characterized by employing various spectro-analytical tools viz. Mass, IR, UV-Vis, TGA, ESR, magnetic measurements, SEM and EDX. The pH-metric titrations with title compound carried out at constant temperature 303 K and 0.1 M KNO3 ionic strength inferred number of dissociable protons in it and further studies with spectrophotometric technique employing Job’s continuous variation method enabled in establishing the composition of its CuII complex. Further DNA cleavage and biological activity studies against Gram-positive and Gram-negative bacteria in present investigation are informative to throw an insight for future scheming of in vitro, in vivo studies. Hyper Chem 7.5 tools were employed to compute the contour maps of frontier orbitals, binding energies, QSAR and molecular parameters. The contour maps of electrostatic potentials for both ionic and molecular forms of title hydrazone were computed to envisage the donor properties.