Non-peripheral and peripheral tetrasubstituted metallophthalocyanines having dichlorophenylthio groups as novel biological active materials for antioxidant, DNA cleavage, antimicrobial, and biofilm inhibition activities

Abstract

We report the preperation of dichlorophenylthio substituted phthalonitrile (2) and its novel non-peripherally tetra sübstituted metallo phthalocyanines {Zn (3), Cu (4) and Mn (5)}. Characterization of newly synthesized compounds was performed by common spectroscopic techniques such as NMR, IR, UV–Vis and mass spectroscopies. The biological properties of the novel non-peripherally dichlorophenylthio substituted Pcs (3–5) and peripherally substituted derivatives (6, 7) were examined for the first time. Comparison of the biological properties of non-peripheral (α- substitution) substituted Pcs with those of peripheral derivatives (β-substution) was made. Among the studied compounds, 3 displayed the highest antioxidant activity as 99.42% at 200 mg/L. DNA cleavage activity of Pcs was also examined and all compounds were found to have DNA cleavage ability. Both peripherally and non-peripherally substituted Pcs showed high antimicrobial activity as tested against pathogenic microorganisms. Microbial cell viability inhibition was also investigated. Additionally, the antimicrobial-photodynamic therapy (APDT) activities of prepared Pcs were performed against Gram-negative bacterium (Escherichia coli) and they exhibited perfect APDT activities as %100. The highest biofilm formation inhibition of S. aureus and P. aeruginosa was 91.28% and 85.74%, respectively, at 250 mg/L with compound 6.