Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues
A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bi...
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| Format: | Article |
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MDPI AG
2019-08-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/17/9/496 |
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| author | Maxim E. Zhidkov Polina A. Smirnova Oleg A. Tryapkin Alexey V. Kantemirov Yuliya V. Khudyakova Olesya S. Malyarenko Svetlana P. Ermakova Valeria P. Grigorchuk Moritz Kaune Gunhild von Amsberg Sergey A. Dyshlovoy |
| author_facet | Maxim E. Zhidkov Polina A. Smirnova Oleg A. Tryapkin Alexey V. Kantemirov Yuliya V. Khudyakova Olesya S. Malyarenko Svetlana P. Ermakova Valeria P. Grigorchuk Moritz Kaune Gunhild von Amsberg Sergey A. Dyshlovoy |
| author_sort | Maxim E. Zhidkov |
| collection | DOAJ |
| description | A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a selective antibiotic (to <i>Pseudomonas aeruginosa</i>) activity and reveals cytotoxicity toward human melanoma, colon, and prostate cancer cells. 3,10-Dibromofascaplysin was able to target metabolic activity of the prostate cancer cells, without disrupting cell membrane’s integrity and had a wide therapeutic window amongst the fascaplysin alkaloids. |
| first_indexed | 2024-04-11T21:49:05Z |
| format | Article |
| id | doaj.art-f67df79895ef404fb68e4a2b2253bea3 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T21:49:05Z |
| publishDate | 2019-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-f67df79895ef404fb68e4a2b2253bea32022-12-22T04:01:18ZengMDPI AGMarine Drugs1660-33972019-08-0117949610.3390/md17090496md17090496Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their AnaloguesMaxim E. Zhidkov0Polina A. Smirnova1Oleg A. Tryapkin2Alexey V. Kantemirov3Yuliya V. Khudyakova4Olesya S. Malyarenko5Svetlana P. Ermakova6Valeria P. Grigorchuk7Moritz Kaune8Gunhild von Amsberg9Sergey A. Dyshlovoy10Department of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, RussiaDepartment of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, RussiaDepartment of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, RussiaDepartment of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, RussiaFederal Scientific Center of the East Asia Terrestrial Biodiversity (Institute of Biology and Soil Science), Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Let Vladivostoku, Vladivostok 690022, RussiaDepartment of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, GermanyDepartment of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, GermanyDepartment of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, RussiaA simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a selective antibiotic (to <i>Pseudomonas aeruginosa</i>) activity and reveals cytotoxicity toward human melanoma, colon, and prostate cancer cells. 3,10-Dibromofascaplysin was able to target metabolic activity of the prostate cancer cells, without disrupting cell membrane’s integrity and had a wide therapeutic window amongst the fascaplysin alkaloids.https://www.mdpi.com/1660-3397/17/9/496total synthesis14-bromoreticulatine3,10-dibromofascaplysinbioactivity |
| spellingShingle | Maxim E. Zhidkov Polina A. Smirnova Oleg A. Tryapkin Alexey V. Kantemirov Yuliya V. Khudyakova Olesya S. Malyarenko Svetlana P. Ermakova Valeria P. Grigorchuk Moritz Kaune Gunhild von Amsberg Sergey A. Dyshlovoy Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues Marine Drugs total synthesis 14-bromoreticulatine 3,10-dibromofascaplysin bioactivity |
| title | Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues |
| title_full | Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues |
| title_fullStr | Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues |
| title_full_unstemmed | Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues |
| title_short | Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues |
| title_sort | total syntheses and preliminary biological evaluation of brominated fascaplysin and reticulatine alkaloids and their analogues |
| topic | total synthesis 14-bromoreticulatine 3,10-dibromofascaplysin bioactivity |
| url | https://www.mdpi.com/1660-3397/17/9/496 |
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