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Catechol thioethers with physiologically active fragments: Electrochemistry, antioxidant and cryoprotective activities.

Bioorganic chemistry (2019-05-28)
Ivan V Smolyaninov, Olga V Pitikova, Eugenia O Korchagina, Andrey I Poddel'sky, Georgy K Fukin, Svetlana A Luzhnova, Andrey M Tichkomirov, Elena N Ponomareva, Nadezhda T Berberova
ABSTRACT

A number of asymmetrical thioethers based on 3,5-di-tert-butylcatechol containing sulfur atom bonding with physiologically active groups in the sixth position of aromatic ring have been synthesized and the electrochemical properties, antioxidant, cryoprotective activities of new thioethers have been evaluated. Cyclic voltammetry was used to estimate the oxidation potentials of thioethers in acetonitrile. The electrooxidation of compounds at the first stage leads to the formation of o-benzoquinones. The antioxidant activities of the compounds were determined using 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) assay, experiments on the oxidative damage of the DNA, the reaction of 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) induced glutathione depletion (GSH), the process of lipid peroxidation of rat liver (Wistar) homogenates in vitro, and iron(II) chelation test. Compounds 1-9 have greater antioxidant effectiveness than 3,5-di-tert-butylcatechol (CatH2) in all assays. The variation of physiologically active groups at sulfur atom allows to regulate lipophilic properties and antioxidant activity of compounds. Thioethers 3, 4 and 7 demonstrate the combination of radical scavenging, antioxidant activity and iron(II) binding properties. The researched compounds 1-9 were studied as possible cryoprotectants of the media for cryopreservation of the Russian sturgeon sperm. Novel cryoprotective additives in cryomedium reduce significantly the content of membrane-permeating agent (DMSO). A cryoprotective effect of an addition of the catechol thioethers depends on the structure of groups at sulfur atom. The cryoprotective properties of compounds 3, 4 and 7 are caused by combination of catechol fragment, bonded by a thioether linker with a long hydrocarbon chain and a terminal ionizable group or with a biologically relevant acetylcysteine residue.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(±)-6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid, 97%
Sigma-Aldrich
11-Mercaptoundecanoic acid, 95%
Sigma-Aldrich
Fluorescein (free acid), Dye content 95 %
Sigma-Aldrich
3,5-Di-tert-butylcatechol, 98%
Sigma-Aldrich
N-Acetylcysteamine, 95%
Sigma-Aldrich
3,5-Di-tert-butyl-o-benzoquinone, 98%
Sigma-Aldrich
9-Mercapto-1-nonanol, 96%
Sigma-Aldrich
4-Acetamidothiophenol, ≥90%
Sigma-Aldrich
11-Mercaptoundecylphosphonic acid, 95%