Design, Structure Affirmation, DNA Binding, Docking Simulation, and Anticancer Activity of an Azo Dye Ligand Derived From 4‐Aminoantipyrine and Its Metal Complexes
Hoda A. El‐Ghamry, Abdalla M. Khedr, Ahmed M. Resha, Eman A. BakrABSTRACT
Synthesis of an azo dye ligand is reported here from coupling of 4‐aminoantipyrine with 4‐ethylphenol, in addition to its Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes. Spectral and analytical techniques were employed to ensure the formation of the ligand and metal complexes. The complexes have been confirmed to have the formulas [Co(HL)Cl(H 2 O)], [Ni(HL)Cl(H 2 O) 2 ]·H 2 O, [Cu(HL) 2 ]·H 2 O, [Zn(HL)(NO 3 )], and [Cd(HL) 2 ]·H 2 O, where HL abbreviates the ligand in deprotonated form. These structures, as confirmed by spectral (i.e. IR, mass, UV–vis, and 1 H‐NMR) and analytical (microanalysis and thermogravimetric analysis) tools, confirmed the construction of the metal complexes in 1L:1M for Co, Ni, and Zn complexes and 2L:1M for Cu and Cd complexes. UV–VCis and viscosity measurements have been applied to study the ligand's and its complexes' DNA binding to SS‐DNA. Additionally, anticancer activity of the target compounds has been investigated against human liver carcinoma cell lines, showing L‐Cd to be the most active against HepG‐2, with an IC 50 of 1.99 ± 0.27 µg/ml, which is comparable to the activity of the standard Cis‐DDP (IC 50 of 1.7 ± 0.34 µg/ml), followed by L‐Zn , with IC 50 = 8.54 ± 0.58 µg/ml. The obtained activity order closely matches the docking results and displayed the potential applications of these compounds as promising anticancer medications.