Surfactant-copper(II) Schiff base complexes: synthesis, structural investigation, DNA interaction, docking studies, and cytotoxic activity.
A series of surfactant-copper(II) Schiff base complexes (1-6) of the general formula, [Cu(sal-R2)2] and [Cu(5-OMe-sal-R2)2], {where, sal=salicylaldehyde, 5-OMe-sal=5-methoxy- salicylaldehyde, and R2=dodecylamine (DA), tetradecylamine (TA), or cetylamine (CA)} have been synthesized and characterized by spectroscopic, ESI-MS, and elemental analysis methods. For a special reason, the structure of one of the complexes (2) was resolved by single crystal X-ray diffraction analysis and it indicates the presence of a distorted square-planar geometry in the complex. Analysis of the binding of these complexes with DNA has been carried out adapting UV-visible-, fluorescence-, as well as circular dichroism spectroscopic methods and viscosity experiments. The results indicate that the complexes bind via minor groove mode involving the hydrophobic surfactant chain. Increase in the length of the aliphatic chain of the ligands facilitates the binding. Further, molecular docking calculations have been performed to understand the nature as well as order of binding of these complexes with DNA. This docking analysis also suggested that the complexes interact with DNA through the alkyl chain present in the Schiff base ligands via the minor groove. In addition, the cytotoxic property of the surfactant-copper(II) Schiff base complexes have been studied against a breast cancer cell line. All six complexes reduced the visibility of the cells but complexes 2, 3, 5, and 6 brought about this effect at fairly low concentrations. Analyzed further, but a small percentage of cells succumbed to necrosis. Of these complexes (6) proved to be the most efficient aptotoxic agent.
a School of Chemistry, Bharathidasan University , Tiruchirappalli 620 024 , Tamil Nadu , India.
Jagadeesan
J
Lakshmipraba
Sankaralingam
S
Arunachalam
Rajadurai Vijay
RV
Solomon
Ponnambalam
P
Venuvanalingam
Anvarbatcha
A
Riyasdeen
Rajakumar
R
Dhivya
Mohammad Abdulkader
MA
Akbarsha
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001667:Binding, Competitive; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000494:pharmacology; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D053938:DNA Fragmentation; D004354:Drug Screening Assays, Antitumor; D004996:Ethidium / Q000737:chemistry; D006801:Humans; D020128:Inhibitory Concentration 50; D007364:Intercalating Agents / Q000737:chemistry; D061986:MCF-7 Cells; D008823:Micelles; D062105:Molecular Docking Simulation; D012545:Schiff Bases / Q000138:chemical synthesis / Q000494:pharmacology; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D014783:Viscosity
D000970:Antineoplastic Agents; D056831:Coordination Complexes; D007364:Intercalating Agents; D008823:Micelles; D012545:Schiff Bases; D013501:Surface-Active Agents; D003300:Copper; D004996:Ethidium
DNA interaction; Surfactant–Schiff base; copper; cytotoxicty; molecular docking