Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides
Natural or synthetic antioxidants with biomimetic fragments protect the functional and structural integrity of biological molecules at a minimum concentration, and may be used as potential chemotherapeutic agents. This paper is devoted to in silico and in vitro evaluation of the antioxidant and cyto...
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| Materiálatiipa: | Artihkal |
| Giella: | English |
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MDPI AG
2022-06-01
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| Ráidu: | Molecules |
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| Liŋkkat: | https://www.mdpi.com/1420-3049/27/12/3961 |
| _version_ | 1827658085029642240 |
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| author | Victoria Osipova Yulia Gracheva Maria Polovinkina Daria Burmistrova Nadezhda Berberova |
| author_facet | Victoria Osipova Yulia Gracheva Maria Polovinkina Daria Burmistrova Nadezhda Berberova |
| author_sort | Victoria Osipova |
| collection | DOAJ |
| description | Natural or synthetic antioxidants with biomimetic fragments protect the functional and structural integrity of biological molecules at a minimum concentration, and may be used as potential chemotherapeutic agents. This paper is devoted to in silico and in vitro evaluation of the antioxidant and cytotoxic properties of synthetic analogues of natural compounds—aromatic oligosulfides. The antiradical and SOD-protective activity of oligosulfides was demonstrated in the reaction with O<sub>2</sub><sup>–•</sup> generated in enzymatic and non-enzymatic systems. It was found that phenol-containing disulfides significantly reduced the accumulation level of hydroperoxides and secondary carbonyl thiobarbituric acid reactive substances, which are primary products of oleic acid peroxidation. The antioxidant efficiency of bis(3,5-di-<i>tert</i>-butyl-4-hydroxyphenyl) disulfide increased over time due to the synergistic action of the 2,6-di-<i>tert</i>-butylphenol fragment and the disulfide linker. The highest cytotoxicity on the A-549 and HCT-116 cell lines was found for bis(3,4-dimethoxyphenyl) disulfide. Significant induction of apoptosis in HCT-116 cells in the presence of bis(3,4-dimethoxyphenyl) disulfide indicates the prospect of its use as an antitumor agent. The significant and moderate dependences revealed between various types of activities of the studied aromatic oligosulfides can be used in the development of a strategy for the synthesis and study of target-oriented compounds with predictable biological activity. |
| first_indexed | 2024-03-09T22:53:56Z |
| format | Article |
| id | doaj.art-28301d55101449aeb4ef7662cec5423a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T22:53:56Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-28301d55101449aeb4ef7662cec5423a2023-11-23T18:14:27ZengMDPI AGMolecules1420-30492022-06-012712396110.3390/molecules27123961Antioxidant Activity and Cytotoxicity of Aromatic OligosulfidesVictoria Osipova0Yulia Gracheva1Maria Polovinkina2Daria Burmistrova3Nadezhda Berberova4Toxicology Research Group of Southern Scientific Centre of Russian Academy of Science, 41 Chekhova Str., 344006 Rostov-on-Don, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1-3, 119991 Moscow, RussiaToxicology Research Group of Southern Scientific Centre of Russian Academy of Science, 41 Chekhova Str., 344006 Rostov-on-Don, RussiaDepartment of Chemistry, Astrakhan State Technical University, 16 Tatisheva Str., 414056 Astrakhan, RussiaDepartment of Chemistry, Astrakhan State Technical University, 16 Tatisheva Str., 414056 Astrakhan, RussiaNatural or synthetic antioxidants with biomimetic fragments protect the functional and structural integrity of biological molecules at a minimum concentration, and may be used as potential chemotherapeutic agents. This paper is devoted to in silico and in vitro evaluation of the antioxidant and cytotoxic properties of synthetic analogues of natural compounds—aromatic oligosulfides. The antiradical and SOD-protective activity of oligosulfides was demonstrated in the reaction with O<sub>2</sub><sup>–•</sup> generated in enzymatic and non-enzymatic systems. It was found that phenol-containing disulfides significantly reduced the accumulation level of hydroperoxides and secondary carbonyl thiobarbituric acid reactive substances, which are primary products of oleic acid peroxidation. The antioxidant efficiency of bis(3,5-di-<i>tert</i>-butyl-4-hydroxyphenyl) disulfide increased over time due to the synergistic action of the 2,6-di-<i>tert</i>-butylphenol fragment and the disulfide linker. The highest cytotoxicity on the A-549 and HCT-116 cell lines was found for bis(3,4-dimethoxyphenyl) disulfide. Significant induction of apoptosis in HCT-116 cells in the presence of bis(3,4-dimethoxyphenyl) disulfide indicates the prospect of its use as an antitumor agent. The significant and moderate dependences revealed between various types of activities of the studied aromatic oligosulfides can be used in the development of a strategy for the synthesis and study of target-oriented compounds with predictable biological activity.https://www.mdpi.com/1420-3049/27/12/3961aromatic oligosulfidesantioxidantradical scavenging activitymetal chelatingcis-9-octadecenoic (oleic) acidliver of Russian sturgeon |
| spellingShingle | Victoria Osipova Yulia Gracheva Maria Polovinkina Daria Burmistrova Nadezhda Berberova Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides Molecules aromatic oligosulfides antioxidant radical scavenging activity metal chelating cis-9-octadecenoic (oleic) acid liver of Russian sturgeon |
| title | Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides |
| title_full | Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides |
| title_fullStr | Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides |
| title_full_unstemmed | Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides |
| title_short | Antioxidant Activity and Cytotoxicity of Aromatic Oligosulfides |
| title_sort | antioxidant activity and cytotoxicity of aromatic oligosulfides |
| topic | aromatic oligosulfides antioxidant radical scavenging activity metal chelating cis-9-octadecenoic (oleic) acid liver of Russian sturgeon |
| url | https://www.mdpi.com/1420-3049/27/12/3961 |
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