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Synthesis of new Salicylaldehyde-based Schiff base Copper (II) complexes and evaluation of their antimicrobial/antioxidant activities


Tonny Kinyua
Eunice Nyawade
Kenneth Ogila

Abstract

Drug resistance has become a major healthcare threat, necessitating the development of new therapeutics. Oxidative stress has also been linked to various illnesses and disorders, increasing the need for potent antioxidant agents. Schiff base compounds have been utilized to develop new drugs due to their potential biological properties. In this study, two new salicylaldehyde – based copper (II) Schiff base complexes were synthesized, characterized and evaluated for their antimicrobial and antioxidant properties. The ligands 2-{[(4-fluorophenyl) imino] methyl} phenol, (L1) and 4-Bromo-2-{[(4-Fluorophenyl) imino] methyl} phenol, (L2) were prepared from 4-fluoroaniline with salicylaldehyde and 5-bromosalicylaldehyde, respectively. They were reacted with copper (II) chloride dihydrate to form [Cu(L1) 2 ]2H 2 O (C1) and [Cu(L2) 2 ]2H 2 O (C2), respectively. Characterization was performed using FT-IR, UV-Vis, 1H NMR, elemental analysis, molar conductance and melting points. Antibacterial activity was assessed in vitro against E. coli, P. aeruginosa, B. subtilis and S. aureus using the disc diffusion method, while the antifungal activity was tested against C. albicans. The antioxidant activity was determined using the DPPH scavenging method. Statistical analysis was conducted using one-way analysis of variance with Tukey’s post hoc test (p < 0.05). Spectroscopic data confirmed coordination of the ligands to the copper (II) ions via their oxygen & nitrogen donor atoms, thereby supporting a squareplanar geometry. Molar conductance studies revealed that the complexes are nonelectrolytes. Biological assays showed that the Cu (II) complexes exhibited significantly higher antimicrobial and antioxidant activities than their free ligands. The brominated Schiff base compounds, L2 and C2, showed significantly higher antimicrobial activity than their nonbrominated analogs, L1 and C1, whereas no significant differences were observed in antioxidant activities. All synthesized compounds showed good antioxidant properties with IC 50 values below 10 μg/mL. Among the synthesized compounds, C2 demonstrated the highest potency and is hence a promising candidate for future clinical applications.


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eISSN: 1561-7645