C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity
This paper presents our attempt to investigate scopes and the limitations of olefin cross-metathesis (CM) reaction in the synthesis of complex C-glycosides of genistein and evaluation of their antiproliferative activities. Novel genistein glycoconjugates were synthesized with the utility of CM react...
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/951392 |
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| author | Aleksandra Rusin Maciej Chrubasik Katarzyna Papaj Grzegorz Grynkiewicz Wiesław Szeja |
| author_facet | Aleksandra Rusin Maciej Chrubasik Katarzyna Papaj Grzegorz Grynkiewicz Wiesław Szeja |
| author_sort | Aleksandra Rusin |
| collection | DOAJ |
| description | This paper presents our attempt to investigate scopes and the limitations of olefin cross-metathesis (CM) reaction in the synthesis of complex C-glycosides of genistein and evaluation of their antiproliferative activities. Novel genistein glycoconjugates were synthesized with the utility of CM reaction initiated by first and second generation of Grubbs catalysts. The relative reactivity of utilized olefins, based on categories proposed by Grubbs, was estimated. In vitro experiments in cancer cell lines showed that the selected derivatives (3a and 3f) exhibited higher antiproliferative potential than the parent compound, genistein, and were able to block the cell cycle in the G2/M phase. The observed mechanism of action of C-glycosidic derivatives was similar to the activity of their O-glycosidic counterparts. These compounds were stable in culture medium. The obtained results show that our approach to genistein modification with application of cross-metathesis reaction allowed to obtain stable glycoconjugates with improved anticancer potential, compared to the parent isoflavone. |
| format | Article |
| id | doaj-art-dec71accff0c499a8ad44309a757c1a7 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-dec71accff0c499a8ad44309a757c1a72025-02-03T01:31:39ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/951392951392C-Glycosidic Genistein Conjugates and Their Antiproliferative ActivityAleksandra Rusin0Maciej Chrubasik1Katarzyna Papaj2Grzegorz Grynkiewicz3Wiesław Szeja4Center for Translational Research and Molecular Biology of Cancer, Maria Sklodowska-Curie Memorial Cancer Center and Institute of Oncology, Wybrzeze AK 15, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandPharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandThis paper presents our attempt to investigate scopes and the limitations of olefin cross-metathesis (CM) reaction in the synthesis of complex C-glycosides of genistein and evaluation of their antiproliferative activities. Novel genistein glycoconjugates were synthesized with the utility of CM reaction initiated by first and second generation of Grubbs catalysts. The relative reactivity of utilized olefins, based on categories proposed by Grubbs, was estimated. In vitro experiments in cancer cell lines showed that the selected derivatives (3a and 3f) exhibited higher antiproliferative potential than the parent compound, genistein, and were able to block the cell cycle in the G2/M phase. The observed mechanism of action of C-glycosidic derivatives was similar to the activity of their O-glycosidic counterparts. These compounds were stable in culture medium. The obtained results show that our approach to genistein modification with application of cross-metathesis reaction allowed to obtain stable glycoconjugates with improved anticancer potential, compared to the parent isoflavone.http://dx.doi.org/10.1155/2013/951392 |
| spellingShingle | Aleksandra Rusin Maciej Chrubasik Katarzyna Papaj Grzegorz Grynkiewicz Wiesław Szeja C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity Journal of Chemistry |
| title | C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity |
| title_full | C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity |
| title_fullStr | C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity |
| title_full_unstemmed | C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity |
| title_short | C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity |
| title_sort | c glycosidic genistein conjugates and their antiproliferative activity |
| url | http://dx.doi.org/10.1155/2013/951392 |
| work_keys_str_mv | AT aleksandrarusin cglycosidicgenisteinconjugatesandtheirantiproliferativeactivity AT maciejchrubasik cglycosidicgenisteinconjugatesandtheirantiproliferativeactivity AT katarzynapapaj cglycosidicgenisteinconjugatesandtheirantiproliferativeactivity AT grzegorzgrynkiewicz cglycosidicgenisteinconjugatesandtheirantiproliferativeactivity AT wiesławszeja cglycosidicgenisteinconjugatesandtheirantiproliferativeactivity |