Role of Knoevenagel condensate pyrazolone derivative Schiff base ligated transition metal complexes in biological assay and cytotoxic efficacy

• Published in: Applied organometallic chemistry 2017-11, Vol.31 (11), p.n/a
• Main Authors: Paulpandiyan, Rajakkani, Arunadevi, Alagarraj, Raman, Natarajan
• Format: Article
• Language: English
• Subjects: Anticancer properties; Binding; Biotechnology; Chemical synthesis; Chemistry; Condensates; Coordination compounds; Deoxyribonucleic acid; DNA; Fungicides; human tumour cell lines; Imines; intercalation mode; Knoevenagel condensate Schiff base; Ligands; Metals; MTT assay; Nickel; nucleolytic cleavage; Pyrazolones; Spectrophotometry; Titration; Toxicity
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.3792

A new bioessential Knoevenagel condensate Schiff base ligand (L) was synthesized by the reaction of 3‐(4‐hydroxy‐3‐methoxybenzyl)pentane‐2,4‐dione and 4‐aminoantipyrine. The ligand forms monomeric divalent transition metal complexes (1–4) which were characterized using spectral and analytical data. All these complexes have the general formula [ML]Cl2, where M = Co(II), Ni(II), Cu(II) and Zn(II). They are electrolytic in nature and adopt square planar geometry. The binding propensity of these complexes with calf thymus DNA was investigated using absorption spectrophotometric titration, cyclic voltammetry and viscosity measurements. The binding constant values imply that the complexes bind with DNA via intercalation mode. The in vitro antibacterial and antifungal activities reveal that the complexes have good antimicrobial efficacy against a set of pathogens. The nucleolytic cleavage activity of these complexes on pUC18 DNA was investigated using agarose gel electrophoresis. Also, the in vitro cytotoxicity of the synthesized complexes against a panel of human tumour cell lines (MCF‐7 and HeLa) and normal cell lines (NHDF and HEK) was assayed using the MTT method. Interestingly, complex 1 exhibits more potent anticancer activity than cisplatin and other complexes. A new series of Knoevenagel condensate Schiff base metal(II) complexes have been synthesized and characterized using spectral and analytical data. They act as strong intercalators, are potential chemical nucleases and show good antimicrobial performance. The complexes show substantial cytotoxic activity towards tumour cell lines. All investigations reveal that the Cu(II) complex has a useful biological profile.