Azophenyl appended Schiff base probe for colorimetric detection of Cu²⁺ in semi‐aqueous medium and live cell imaging

Abstract

A phenylazo appended ortho-vanillin Schiff base scaffold (HAZ) has been used for selective colorimetric sensing of Cu 2+ in semi-aqueous medium (methanol-water, 1:1, v/v) in the presence of 16 cations and 20 anions, and the limit of detection is 1.8 Â 10 À7 M. The structures of HAZ and Cu (II) complex, [Cu (AZ) 2 ], have been characterised by spectroscopic data (UV-Vis, Fourier transform infrared and electron paramagnetic resonance) and established by the single crystal X-ray diffraction measurement. The Job's plot from the absorption studies has also confirmed the 1:2 stoichiometry of Cu 2+ :HAZ. The absorption spectrum of [Cu (AZ) 2 ] has returned to the spectrum of HAZ on the addition of Na 2 EDTA solution which is again recovered upon the addition of Cu 2+ solution. Discrete Fourier transform computations were carried out using the coordinates of the X-ray structures of the compounds, and the molecular functions were used to correlate the solution spectroscopic properties. In addition to this, the probe is treated on MDA-MB 231 breast cancer cells to check the cytotoxicity. The probe is used for the detection of trace quantity of Cu 2+ in the cancer cell. K E Y W O R D Scell imaging assay, cytotoxicity study, colorimetric sensor of Cu 2+ ions, phenylazo appended ortho-vanillin Schiff base, X-ray structures

High anticancer activity in short response time exhibited by a new azobenzene derivative and its copper complex

“…The Cu-O (1.880(17) Å) bond distance is shorter than Cu-N bond (1.995(2) Å), which are comparable with reported data. 31 The azo and the imine moieties also possess a trans-conformation similar to HL. But the molecule is significantly twisted along N1-C8 bond with respect to the coordination core, which is reflected from the torsion angle (C7-N1-C8-C13), 119.3(3) and (Cu1-N1-C8-C13), À67.3(3) .…”

“…The results have been compared with previously reported ligand HAZ and its copper(II) complex-Cu (AZ) 2 . 31 The interaction of the novel compounds with estrogen receptor, hERα, has also been demonstrated by the docking analysis (PDB ID: 3ERT, PDBDOI: 10.2210/ pdb3ERT/pdb). The results are very promising, and they support the experimental observations.…”