Biological Activity of Novel Organotin Compounds with a Schiff Base Containing an Antioxidant Fragment

• Published in: International journal of molecular sciences Vol. 24; no. 3; p. 2024
• Main Authors: Antonenko, Taisiya A, Gracheva, Yulia A, Shpakovsky, Dmitry B, Vorobyev, Mstislav A, Mazur, Dmitrii M, Tafeenko, Victor A, Oprunenko, Yury F, Shevtsova, Elena F, Shevtsov, Pavel N, Nazarov, Alexey A, Milaeva, Elena R
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 19.01.2023; MDPI
• Subjects: Antineoplastic Agents - pharmacology; antioxidant activity; Antioxidants; Antioxidants - pharmacology; antiproliferative activity; Antiproliferatives; Apoptosis; Biological activity; Cell cycle; Cell lines; Chemical bonds; Crystallography, X-Ray; Crystals; Humans; Hydrogen bonding; Hydrogen bonds; Imines; Ligands; Linoleic acid; Lipoxygenase; Liquid oxygen; Molecular structure; NMR; Nuclear magnetic resonance; organotin complexes; Organotin Compounds - chemistry; Organotin Compounds - pharmacology; Oxidation; Phenols; Reducing agents; Schiff base; Schiff Bases - chemistry; Schiff Bases - pharmacology; Spectrophotometry; Spectrum analysis; Schiff base; apoptosis; cell cycle; antioxidant activity; antiproliferative activity; organotin complexes
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms24032024

A series of novel organotin(IV) complexes on the base of 2-(N-3',5'-di- -butyl-4'-hydroxyphenyl)-iminomethylphenol ( ) of formulae Me SnBr (L) ( ), Bu SnCl (L) ( ), Ph SnCl (L) ( ), Ph SnCl (L) ( ) Ph SnBr(L) ( ) were synthesized and characterized by H, C, Sn NMR, IR, ESI-MS and elemental analysis. The crystal structures of initial and complex were determined by XRD method. It was found that crystallizes in the orthorhombic syngony. The distorted octahedron geometry around Sn center is observed in the structure of complex . Intra- and inter-molecular hydrogen bonds were found in both structures. The antioxidant activity of new complexes as reducing agents, radical scavengers and lipoxygenase inhibitors was estimated spectrophotometrically in CUPRAC and DPPH tests (compounds and were found to be the most active in both methods), and in the process of enzymatic oxidation in vitro of linoleic acid under the action of lipoxygenase LOX 1-B (EC > 33.3 μM for complex ). Furthermore, compounds have been investigated for their antiproliferative activity in vitro towards HCT-116, MCF-7 and A-549 and non-malignant WI-38 human cell lines. Complexes and demonstrated the highest activity. The plausible mechanisms of the antiproliferative activity of compounds, including the influence on the polymerization of Tb+MAP, are discussed. Some of the synthesized compounds have also actively induced apoptosis and blocked proliferation in the cell cycle G2/M phase.