Synthesis, characterization of 4-{[(E)-{2-hydroxy-3-[(Z)-1,3-thiazol-2-yldiazeneyl]napthalen-1-yl}methylidene]amino}benzoic acid and its transition metal complexes; biopharmaceutical activities and electrochemical detection of ciplactin

Abstract

A Schiff base derivative, 4-{[(E)-{2‑hydroxy-3-[(Z)-1,3-thiazol-2-yldiazeneyl]napthalen-1-yl}methylidene]amino}benzoic acid (ENB) and some of its transition metal complexes were synthesised. The structure of the ENB and its complexes were characterised by NMR, FT-IR, mass spectra, TGA, UV–visible, PXRD and ESR techniques. Physico-chemical data suggest an octahedral geometry nature. Molecular docking for all the synthesised compounds has been performed to predict the binding affinity. The [Ni(ENB)2] exhibited excellent binding score of -284.32 kcal/mol In vitro cytotoxicity activities on lungs cell line A459 exhibited significant IC50values and the results indicated that [Co(ENB)2] is a stronger antioxidant agent. Electrochemical detection of bioactive drug ciplactin using a modified electrode, MWCNT-[Co(ENB)2]/GCE showed an excellent sensing ability with a long linear range 10-90 µmol/L, sensitivity 0.4765 µAµM−1cm−2 and its LOD is 3.333 µmol/L in PBS pH 7. Further, the modified electrodehas more stability and less leaching property in the detection system.