2,4‐Dihydroxy‐5‐[(5‐mercapto‐1H‐1,2,4‐triazole‐3‐yl)diazenyl]benzaldehyde acetato, chloro and nitrato Cu(II) complexes: Synthesis, structural characterization, DNA binding and anticancer and antimicrobial activity

Abstract

Acetato, chloro and nitrato Cu(II) complexes of a novel azo compound, namely 2,4‐dihydroxy‐5‐[(5‐mercapto‐1H‐1,2,4‐triazole‐3‐yl)diazenyl]benzaldehyde, have been prepared. The stoichiometry, stereochemistry and bonding fashion of these copper chelates were deduced via elemental analyses, spectral methods and conductivity and magnetic measurements. Infrared spectral data confirmed the participation of azo N atom and the deprotonated OH group. UV–visible spectral data and magnetic measurements indicated octahedral stereo‐structure for the acetato and nitrato compounds and square planer for the chloro compound. Thermogravimetric analysis was applied to investigate the thermal degradation of the metal chelates. The thermo‐kinetic parameters were computed. The molecular modeling technique was used to support the predicted geometry of the prepared chelates. The interaction between the Cu(II) complexes and calf thymus DNA was studied using two techniques: absorption and viscosity measurements. The values of binding constant obtained from the absorption spectral method were calculated and found to be 4.23 × 104, 26.93 × 104, 13.01 × 104 and 5.36 × 104 M−1 for ligand and acetato, chloro and nitrato complexes, respectively. The antimicrobial activities were evaluated against various bacterial and fungi strains. The in vitro antitumor efficacy of the synthesized compounds was investigated against the HEPG2 cell line.

Synthesis, structural identification, DNA interaction and biological studies of divalent Mn, Co and Ni chelates of 3‐amino‐5‐mercapto‐1,2,4‐triazole azo ligand

“…-triazole-3-yl)diazenyl]benzaldehyde ( Figure S1) has been isolated by coupling of 3-amino-5-mercapto-1,2,4-triazole with 2,4-dihydroxybenzaldehyde according to the previously cited method. [24]…”

“…Over the years, these compounds are found to possess extensive implementations in various biological applications, especially antimicrobial, anticancer and antimalarial therapy. [18][19][20][21][22] Owing to the above aforesaid significance of azo-containing ligands and in continuance to our research group interests in syntheses of azo compounds based on 3-amino-5-mercapto-1,2,4-triazole which we prospect to be good acting as anticancer, [23,24] we report herein the syntheses and study of new Mn (II), Co (II) and Ni (II) chelates of the azo ligand derived from the coupling of 3-amino-5-mercapto-1,2,4-triazole and 2,4-dihydroxybenzaldehyde. The structural characterization were achieved applying the alternative analytical and spectral tools.…”

Fabrication, spectroscopic characterization, calf thymus DNA binding investigation, antioxidant and anticancer activities of some antibiotic azomethine Cu(II), Pd(II), Zn(II) and Cr(III) complexes

“…Metals like zinc(II), chromium(III) and copper(II) have great affinity for coordination because of their small size and high nuclear charge. The development of metal–drug adducts as chemotherapeutic agents basically depends on the ability of the metallodrug to provoke DNA cleavage . It is worth mentioning that metal chelate pharmacological efficacy mainly depends on the nature of metal ions and ligands.…”

In-Vitro Antimicrobial Screening and Coordination Behavior of Metals Based Bidentate Compounds

“…Because of the transfer of charge from the ligand to the metal, a strong band was observed at 29738-29813 cm -1 . The electron spectrum of all complexes of Cu(II) presented absorption bands [41] 8697-8637 and 17623-17672 cm -1 order, that may be given along transition 2 Eg → 2 T2g. The band of high energy at 29781-29818 cm -1 was because of the prohibition of ligand→metal charge transfer (CT) process.…”