Cytotoxic and Luminescent Properties of Novel Organotin Complexes with Chelating Antioxidant Ligand

Abstract

A novel polydentate chelating antioxidant ligand and series of organotin complexes on its base were synthesized and characterized by NMR 1H, 13C, 119Sn, IR spectroscopy, X-ray, and elemental analysis. Their antioxidant activity was evaluated in DPPH and NBT-tests, and as lipoxygenase inhibitory activity. It was shown that ligand alone is a radical scavenger, while introducing tin in the structure of the compound significantly decreases its activity. For the ligand alone the ability to strongly suppress the formation of advanced glycation end products (AGEs) was shown, which may be associated with the established antiradical activity. All synthesized compounds appeared to be moderate lipoxygenase inhibitors. The stability of compounds to hydrolysis under different pH was estimated. The ligand undergoes decomposition after about an hour, while organotin complexes on its base demonstrate vast stability, showing signs of decomposition only after 5 h of experimentation. Cytotoxicity of compounds was studied by standard MTT-test, which showed unorthodox results: the ligand itself demonstrated noticeable cytotoxicity while the introduction of organotin moiety either did not affect the toxicity levels or reduced them instead of increasing. Organotin complexes possess luminescence both as powders and DMSO solutions, its quantum yields reaching 67% in DMSO. The combination of luminescence with unique cytotoxic properties allows us to propose the synthesized compounds as perspective theranostic agents.

Molybdenum-maltolate as a molybdopterin mimic for bioinspired oxidation reaction

“…15 This is followed by the oxidation of xanthine to uric acid following a superoxide radical (O 2 ˙ − ) mechanism. 16 Inspired by this reaction in nature, we carried out a similar oxidation reaction of hypoxanthine using 1 . The oxidation of hypoxanthine to xanthine was achieved by treating hypoxanthine with 1 mmol TBHP as the oxidant and 5 mol% of 1 taking in CH 3 CN : H 2 O (1 : 1) mixture at room temperature.…”

“…Xanthine oxidase is known to catalyze xanthine to uric acid, yielding a superoxide radical anion (ROS, O 2 ˙ − ). 16 Further, ROS production can be spectroscopically monitored by the reduction of nitro-blue tetrzolium (NBT). 17 To a stirred DMSO solution of NBT, compound 1 and TBHP were added, and absorption spectra were recorded over a period of 40 min (ESI, Fig.…”

1-(2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl) Quinolin-1-ium Bromide

“…This provides an opportunity to combine the quinoline and 2,6-DTBP fragments into a quaternary ammonium molecule with the goal of unlocking a synergistic effect toward enhanced On the other hand, the research on 2,6-tert-butyl phenol (2,6-DTBP) derivatives is limited and is mainly focused on its antioxidative properties. For example, in a study by Milaeva et al, the 2,6-DTBP fragment was included in a series of organotin complexes showing antioxidative, luminescent, and cytotoxic properties [26]. Moreover, Berberova et al demonstrated the antioxidative and cytotoxic activity of aromatic oligosulfides bearing the same fragment [27].…”