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

Zhidkov M.E., Smirnova P.A., Tryapkin O.A., Kantemirov A.V., Khudyakova Y.V., Malyarenko O.S., Ermakova S.P., Grigorchuk V.P., Kaune M., von Amsberg G., Dyshlovoy S.A.

В журнале Marine Drugs

Год: 2019 Том: 17 Номер: 9 ArticleID: 496

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.

DOI 10.3390/md17090496