Triphenylphosphine Thiolate Gold(I) Complexes with Redox-Active Schiff Bases: Synthesis, Electrochemical Properties, and Biological Activity

I. V. Smolyaninov; Смолянинов И. В.; D. A. Burmistrova; Бурмистрова Д. А.; N. P. Pomortseva; Поморцева Н. П.; M. A. Polovinkina; Половинкина М. А.; O. P. Demidov; Демидов О. П.; N. R. Al’myasheva; Альмяшева Н. Р.; A. I. Poddel’skii; Поддельский А. И.; N. T. Berberova; Берберова Н. Т.

doi:10.31857/S0132344X23600121

Triphenylphosphine Thiolate Gold(I) Complexes with Redox-Active Schiff Bases: Synthesis, Electrochemical Properties, and Biological Activity

Authors: Smolyaninov I.V.¹, Burmistrova D.A.¹, Pomortseva N.P.¹, Polovinkina M.A.², Demidov O.P.³, Al’myasheva N.R.⁴, Poddel’skii A.I.⁵, Berberova N.T.¹
Affiliations:
1. Astrakhan State Technical University, Astrakhan, Russia
2. Federal Research Center, Southern Scientific Center, Russian Academy of Sciences, Rostov-on-Don, Russia
3. North Caucasus Federal University, Stavropol, Russia
4. Gause Institute of New Antibiotics, Moscow, Russia
5. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhny Novgorod, Russia
Issue: Vol 49, No 9 (2023)
Pages: 565-581
Section: Articles
URL: https://journals.eco-vector.com/0132-344X/article/view/667483
DOI: https://doi.org/10.31857/S0132344X23600121
EDN: https://elibrary.ru/WBPETP
ID: 667483

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Abstract

New gold(I) phosphine thiolate complexes [(Ph3P)Au(SLn)] I–V with Schiff bases LnSH containing
redox-active catechol, phenol, or quinone methide moieties were synthesized and characterized. The
molecular structure of compound I in the crystalline state was established by X-ray diffraction (CCDC
no. 2237815). The electrochemical behavior of compounds I–V was studieв by cyclic voltammetry. The proposed
electrooxidation mechanism of the complexes involves the Au–S bond cleavage, the disulfide formation,
as well as the oxidation of the redox active group of the ligand. In the cathode region, complexes I–III
tend to form relatively stable monoanionic species. The radical scavenging activity of complexes decreases in
comparison to free ligands in the reactions with synthetic radicals and the CUPRAC test. Compounds I, II,
IV, and V have no clear-cut effect on the promoted DNA damage; however, they show antioxidant action
in the non-enzymatic lipid peroxidation of rat liver homogenate. Compounds I–V demonstrate a weak antibacterial
activity against Staphylococcus aureus strains. The gold(I) complexes cytotoxicity was studied against
A-549, MCF-7, and HTC-116 cancer cell lines using MTT assay. The test compounds are characterized by
higher selectivity to certain types of cells than the sulfur-containing Schiff bases. The presence of quinone
methide moiety in the ligand in case of V significantly increases the cytotoxicity against all of the cell lines.

Keywords

gold(I) thiolate complexes, redox active Schiff bases, X-ray diffraction, cyclic voltammetry, antioxidant activity, cytotoxicity

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