Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones
A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-<i>O</i>-acetyl <span style="font-variant: small-caps;">d</span>-glucose, <span style="font-varian...
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| Format: | Article |
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MDPI AG
2020-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/16/3577 |
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| author | Yuri E. Sabutski Ekaterina S. Menchinskaya Ludmila S. Shevchenko Ekaterina A. Chingizova Artur R. Chingizov Roman S. Popov Vladimir A. Denisenko Valery V. Mikhailov Dmitry L. Aminin Sergey G. Polonik |
| author_facet | Yuri E. Sabutski Ekaterina S. Menchinskaya Ludmila S. Shevchenko Ekaterina A. Chingizova Artur R. Chingizov Roman S. Popov Vladimir A. Denisenko Valery V. Mikhailov Dmitry L. Aminin Sergey G. Polonik |
| author_sort | Yuri E. Sabutski |
| collection | DOAJ |
| description | A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-<i>O</i>-acetyl <span style="font-variant: small-caps;">d</span>-glucose, <span style="font-variant: small-caps;">d</span>-galactose, <span style="font-variant: small-caps;">d</span>-xylose, and <span style="font-variant: small-caps;">l</span>-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC<sub>50</sub> values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (<i>Staphylococcus aureus</i>, <i>Bacillus cereus</i>), Gram-negative bacteria (<i>Pseudomonas aeruginosa</i> and <i>Escherichia coli</i>), and fungus <i>Candida albicans</i> by the agar diffusion method. The most effective juglone conjugates with <span style="font-variant: small-caps;">d</span>-xylose or <span style="font-variant: small-caps;">l</span>-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown. |
| first_indexed | 2024-03-10T17:52:43Z |
| format | Article |
| id | doaj.art-4d8fa0a23f3c4979b906b4a660d36265 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T17:52:43Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4d8fa0a23f3c4979b906b4a660d362652023-11-20T09:17:37ZengMDPI AGMolecules1420-30492020-08-012516357710.3390/molecules25163577Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-NaphthoquinonesYuri E. Sabutski0Ekaterina S. Menchinskaya1Ludmila S. Shevchenko2Ekaterina A. Chingizova3Artur R. Chingizov4Roman S. Popov5Vladimir A. Denisenko6Valery V. Mikhailov7Dmitry L. Aminin8Sergey G. Polonik9G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences. Prospekt 100-let Vladivostoku 159, 690022 Vladivostok, RussiaA series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-<i>O</i>-acetyl <span style="font-variant: small-caps;">d</span>-glucose, <span style="font-variant: small-caps;">d</span>-galactose, <span style="font-variant: small-caps;">d</span>-xylose, and <span style="font-variant: small-caps;">l</span>-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC<sub>50</sub> values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (<i>Staphylococcus aureus</i>, <i>Bacillus cereus</i>), Gram-negative bacteria (<i>Pseudomonas aeruginosa</i> and <i>Escherichia coli</i>), and fungus <i>Candida albicans</i> by the agar diffusion method. The most effective juglone conjugates with <span style="font-variant: small-caps;">d</span>-xylose or <span style="font-variant: small-caps;">l</span>-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown.https://www.mdpi.com/1420-3049/25/16/35771,4-naphthoquinonesquinoid compoundsthioglycosidesquinone-sugar conjugatescytotoxic activityantibiotic activity |
| spellingShingle | Yuri E. Sabutski Ekaterina S. Menchinskaya Ludmila S. Shevchenko Ekaterina A. Chingizova Artur R. Chingizov Roman S. Popov Vladimir A. Denisenko Valery V. Mikhailov Dmitry L. Aminin Sergey G. Polonik Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones Molecules 1,4-naphthoquinones quinoid compounds thioglycosides quinone-sugar conjugates cytotoxic activity antibiotic activity |
| title | Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones |
| title_full | Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones |
| title_fullStr | Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones |
| title_full_unstemmed | Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones |
| title_short | Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones |
| title_sort | synthesis and evaluation of antimicrobial and cytotoxic activity of oxathiine fused quinone thioglucoside conjugates of substituted 1 4 naphthoquinones |
| topic | 1,4-naphthoquinones quinoid compounds thioglycosides quinone-sugar conjugates cytotoxic activity antibiotic activity |
| url | https://www.mdpi.com/1420-3049/25/16/3577 |
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