Synthesis, spectral characterization and biological activities of Ag(I), Pt(IV) and Au(III) complexes with novel azo dye ligand (N, N, O) derived from 2-amino-6-methoxy benzothiazole

• Published in: Chemical papers Vol. 76; no. 5; pp. 2777 - 2810
• Main Authors: Kyhoiesh, Hussein Ali Kadhim, Al-Adilee, Khalid J.
• Format: Journal Article
• Language: English
• Published: Warsaw Versita 01.05.2022; Springer Nature B.V
• Subjects: Antiinfectives and antibacterials; Antioxidants; Azo compounds; Azo dyes; Benzoic acid; Biochemistry; Biotechnology; Cancer; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Coordination compounds; Crystal structure; Differential thermal analysis; Endometrial cancer; Endothelial cells; Fungi; Fungicides; Gold; Group theory; Industrial Chemistry/Chemical Engineering; Kinases; Ligands; Magnetic properties; Mass spectra; Materials Science; Medicinal Chemistry; Mutation; Nitrogen; NMR; Nuclear magnetic resonance; Original Paper; Platinum; Rings (mathematics); Scavenging; Silver; Antimicrobial; MFE-296; XRD; Antioxidant; Benzothiazole; Molecular docking
• ISSN: 0366-6352; 2585-7290; 1336-9075
• DOI: 10.1007/s11696-022-02072-9

The novel ligand 2-[2 ' -(6-methoxybenzothiazolyl)azo]-3,5-dimethyl benzoic acid (6-MBTAMB), derived from 2-amino-6-methoxy benzothiazole, has been used to synthesize a series of new metal complexes of Ag(I), Pt(IV) and Au(III). The metal complexes were characterized by elemental analyses (CHNS), molar conductivity, crystal structure (XRD), spectroscopic techniques: FT-IR, 1 H NMR, 13 C NMR, UV–Vis, mass spectra, thermal analysis (TG–DTA), FE-SEM and magnetic properties. Results confirmed that the azo dye ligand behaves a tridentate and coordinates to the metal ion via nitrogen atom of azomethine group of heterocyclic benzothiazole ring, nitrogen atom of the azo group which is the farthest of the benzothiazole molecule and carboxylic oxygen. Antimicrobial properties of all newly synthesized azo compounds are also demonstrated against bacterial pathogenic organisms and fungi. These complexes are more effective against bacteria and less effective against fungi compared to standard antibacterial drugs (novobiocin) and antifungal drugs (cycloheximide). By using the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging test, it was discovered that the complexes had good antioxidant properties. In addition, the (6-MBTAMB) and metal complexes were docked with the crystal structure of FGF Receptor 2 (FGFR2) kinase domain harboring the pathogenic gain of function K659E mutation identified in endometrial cancer using the molecular operating environment (MOE) module. In vitro studies on human endometrial cancer cell lines (MFE-296) as well as healthy human umbilical vein endothelial cells (HUVEC) show uptake of the intact compounds by the cancer cells and increased activity against the cancer cells. Graphical abstract