The Synthesis and Biological Activity of Organotin Complexes with Thio-Schiff Bases Bearing Phenol Fragments

Author:

Smolyaninov Ivan V.1ORCID,Poddel’sky Andrey I.2ORCID,Burmistrova Daria A.1,Voronina Yulia K.3ORCID,Pomortseva Nadezhda P.1,Polovinkina Maria A.4ORCID,Almyasheva Nailya R.5ORCID,Zamkova Maria A.6,Berberova Nadezhda T.1,Eremenko Igor L.3ORCID

Affiliation:

1. Chemistry Department, Astrakhan State Technical University, 16 Tatisheva Str., 414056 Astrakhan, Russia

2. Chemistry Department, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

3. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prospekt 31, 119071 Moscow, Russia

4. Toxicology Research Group of Southern Scientific Centre of Russian Academy of Science, 41 Chekhova Str., 344006 Rostov-on-Don, Russia

5. Gause Institute of New Antibiotics, 11/1 Bolshaya Pirogovskaya Str., 119021 Moscow, Russia

6. N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of the Russian Federation, Kashirskoe sh., 24, 115478 Moscow, Russia

Abstract

A number of novel di- and triorganotin(IV) complexes 1–5 (Ph2SnL1, Ph2SnL2, Et2SnL2, Ph3SnL3, Ph3SnL4) with mono- or dianionic forms of thio-Schiff bases containing antioxidant sterically hindered phenol or catechol fragments were synthesized. Compounds 1–5 were characterized by 1H, 13C NMR, IR spectroscopy, and elemental analysis. The molecular structures of complexes 1 and 2 in the crystal state were established by single-crystal X-ray analysis. The antioxidant activity of new complexes as radical scavengers was estimated in DPPH and ABTS assays. It was found that compounds 4 and 5 with free phenol or catechol fragments are more active in these tests than complexes 1–3 with tridentate O,N,S-coordinated ligands. The effect of compounds 1–5 on the promoted oxidative damage of the DNA by 2,2’-azobis(2-amidinopropane) dihydrochloride and in the process of rat liver (Wistar) homogenate lipid peroxidation in vitro was determined. Complexes 4 and 5 were characterized by more pronounced antioxidant activity in the reaction of lipid peroxidation in vitro than compounds 1–3. The antiproliferative activity of compounds 1–5 was investigated against MCF-7, HTC-116, and A-549 cell lines by an MTT test. The values of IC50 are significantly affected by the presence of free antioxidant fragments and the coordination site for binding.

Funder

Russian Science Foundation

Publisher

MDPI AG

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Computer Science Applications,Spectroscopy,Molecular Biology,General Medicine,Catalysis

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