Design amino acids Schiff base ligands and their Cu(II) and Zn(II) complexes as potent anticancer agent on human lung carcinoma, efficient CT-DNA binder, antibacterial and mesomorphic properties

• Published in: Journal of molecular structure 2024-12, Vol.1317, p.139075, Article 139075
• Main Authors: Kharpan, Bandashisha, Pyngrope, Hunshisha, chetia, Jagritima, Bhattacharyya, Mayuri, Shyam, Abhijit, Wangkheimayum, Jayalaxmi, Pramanik, Harun A.R., Paul, Pradip C., Majaw, Suktilang, Bhattacharjee, Amitabha, Mondal, Paritosh
• Format: Article
• Language: English
• Subjects: Amino acid; Antibacterial; Anticancer; CT-DNA binding; DFT; Schiff base
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.139075

•Synthesis of Schiff base ligands, of the type Potassium (E)−4-((4-(hexadecyloxy)−2-hydroxybenzylidene)amino)butanoate (HL1) and Potassium (E)−6-((4-(hexadecyloxy)−2-hydroxybenzylidene)amino)hexanoate (HL2) and their corresponding copper(II) and zinc(II) complexes.•The complexes have potent anticancer activity against A549 cell line and antibacterial property against Staphylococcus aureus and Escherichia coli.•The complexes exhibit effective interaction with CT-DNA.•The Schiff base ligands possess multiple texture of SmA and columnar mesophase.•DFT study was carried out to obtain the optimized geometry of the compounds. A new mesogenic amino acid Schiff base ligands of the type Potassium (E)-4-((4-(hexadecyloxy)-2-hydroxybenzylidene)amino)butanoate (HL1) and Potassium (E)-6-((4-(hexadecyloxy)-2-hydroxybenzylidene)amino)hexanoate (HL2) and their copper(II) and zinc(II) complexes have been successfully synthesized and characterized by various elemental analyses, UV–visible, FT-IR, 1HNMR , 13CNMR , ESI-MS and thermogravimetric analysis (TGA). Both the ligands were found to exhibit mesophase with multiple textures as revealed from the polarizing optical microscope (POM) and differential scanning calorimetry (DSC). The metal complexes were found to exhibit efficient CT-DNA interaction and antibacterial activity against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli). The complexes were assessed for their in-vitro anticancer efficacy against A549 cell line and findings indicate notable cytotoxicity effect which is comparable to that of standard drug, cisplatin. The Density Functional Theory (DFT) study of the compounds was carried out by using LanL2DZ and 6–31 G (d, p) basis set with meta-hybrid Truhlar's functional M06–2X in order to obtain the optimized geometry. [Display omitted]