2. Academic Validation
  3. Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues

Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues

  • Mar Drugs. 2019 Aug 25;17(9):496. doi: 10.3390/md17090496.
Maxim E Zhidkov 1,  Polina A Smirnova 2,  Oleg A Tryapkin 2,  Alexey V Kantemirov 2,  Yuliya V Khudyakova 3,  Olesya S Malyarenko 3,  Svetlana P Ermakova 3,  Valeria P Grigorchuk 4,  Moritz Kaune 5,  Gunhild von Amsberg 5 6,  Sergey A Dyshlovoy 2 3 5 6
Affiliations

Affiliations

  • 1 Department of organic chemistry and Laboratory of biologically active compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, Russia. [email protected].
  • 2 Department of organic chemistry and Laboratory of biologically active compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, Russia.
  • 3 G.B. Elyakov Pacific Institute of Bioorganic Chemistry, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, Russia.
  • 4 Federal 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, Russia.
  • 5 Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, Germany.
  • 6 Martini-Klinik Prostate Cancer Center, University Hospital Hamburg-Eppendorf, 20246 Hamburg, Germany.
PMID: 31450717 DOI: 10.3390/md17090496
Abstract

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 Pseudomonas aeruginosa) 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.

Keywords

14-bromoreticulatine; 3,10-dibromofascaplysin; bioactivity; total synthesis.

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