Synthesis, X-ray Structure and Biological Studies of New Self-Assembled Cu(II) Complexes Derived from s-Triazine Schiff Base Ligand

Abstract

The two ligands 2-(1-(2-(4,6-dimorpholino-1,3,5-triazin-2-yl)hydrazono)ethyl)aniline (DMAT) and 2-(1-(2-(4,6-dimorpholino-1,3,5-triazin-2-yl)hydrazono)ethyl)phenol (DMOHT) were used to synthesize three heteroleptic Cu(II) complexes via a self-assembly technique. The structure of the newly synthesized complexes was characterized using elemental analysis, FTIR and X-ray photoelectron spectroscopy (XPS) to be [Cu(DMAT)(H2O)(NO3)]NO3.C2H5OH (1), [Cu(DMOT)(CH3COO)] (2) and [Cu(DMOT)(NO3)] (3). X-ray single-crystal structure of complex 1 revealed a hexa-coordinated Cu(II) ion with one DMAT as a neutral tridentate NNN-chelate, one bidentate nitrate group and one water molecule. In the case of complex 2, the Cu(II) is tetra-coordinated with one DMOT as an anionic tridentate NNO-chelate and one monodentate acetate group. The antimicrobial, antioxidant and anticancer activities of the studied compounds were examined. Complex 1 had the best anticancer activity against the lung carcinoma A-549 cell line (IC50 = 5.94 ± 0.58 µM) when compared to cis-platin (25.01 ±2.29 µM). The selectivity index (SI) of complex 1 was the highest (6.34) when compared with the free ligands (1.3–1.8), and complexes 2 (0.72) and 3 (2.97). The results suggested that, among those compounds studied, complex 1 is the most promising anticancer agent against the lung carcinoma A-549 cell line. In addition, complex 1 had the highest antioxidant activity (IC50 = 13.34 ± 0.58 µg/mL) which was found to be comparable to the standard ascorbic acid (IC50 = 10.62 ± 0.84 µg/mL). Additionally, complex 2 showedbroad-spectrum antimicrobial action against the microbes studied. The results revealed it to possess the strongest action of all the three complexes against B. subtilis. The MIC values found are 39.06, 39.06 and 78.125 μg/mL for complexes 1–3, respectively.