(5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity
For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes....
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| Format: | Article |
| Language: | English |
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MDPI AG
2024-01-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2024/1/M1758 |
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| author | Regina A. Tuktarova Lilya U. Dzhemileva Usein M. Dzhemilev |
| author_facet | Regina A. Tuktarova Lilya U. Dzhemileva Usein M. Dzhemilev |
| author_sort | Regina A. Tuktarova |
| collection | DOAJ |
| description | For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity of (5Z,9Z)-14-[(3,28-dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic acid against tumor cells Jurkat, K562, U937 and HL60 was established. This compound is also an inducer of apoptosis, affects the cell cycle and inhibits human topoisomerase I. |
| first_indexed | 2024-04-24T17:59:31Z |
| format | Article |
| id | doaj.art-88c03a5a318f456288363608d7c9d57c |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-04-24T17:59:31Z |
| publishDate | 2024-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-88c03a5a318f456288363608d7c9d57c2024-03-27T13:56:34ZengMDPI AGMolbank1422-85992024-01-0120241M175810.3390/M1758(5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic ActivityRegina A. Tuktarova0Lilya U. Dzhemileva1Usein M. Dzhemilev2Chemical Engineering Center, ITMO University, 49A Kronverksky Prospekt, 197101 Saint-Petersburg, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaFor the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity of (5Z,9Z)-14-[(3,28-dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic acid against tumor cells Jurkat, K562, U937 and HL60 was established. This compound is also an inducer of apoptosis, affects the cell cycle and inhibits human topoisomerase I.https://www.mdpi.com/1422-8599/2024/1/M1758hybrid moleculesoleanolic acid(5<i>Z</i>,9<i>Z</i>)-dienoic acidcytotoxic activityapoptosiscell cycle |
| spellingShingle | Regina A. Tuktarova Lilya U. Dzhemileva Usein M. Dzhemilev (5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity Molbank hybrid molecules oleanolic acid (5<i>Z</i>,9<i>Z</i>)-dienoic acid cytotoxic activity apoptosis cell cycle |
| title | (5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity |
| title_full | (5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity |
| title_fullStr | (5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity |
| title_full_unstemmed | (5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity |
| title_short | (5<i>Z</i>,9<i>Z</i>)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity |
| title_sort | 5 i z i 9 i z i 14 3 28 dioxoolean 12 en 28 yl oxy tetradeca 5 9 dienoic acid with cytotoxic activity |
| topic | hybrid molecules oleanolic acid (5<i>Z</i>,9<i>Z</i>)-dienoic acid cytotoxic activity apoptosis cell cycle |
| url | https://www.mdpi.com/1422-8599/2024/1/M1758 |
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