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

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.

SUBMITTER: Zhidkov ME 

PROVIDER: S-EPMC6780422 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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

Zhidkov Maxim E ME   Smirnova Polina A PA   Tryapkin Oleg A OA   Kantemirov Alexey V AV   Khudyakova Yuliya V YV   Malyarenko Olesya S OS   Ermakova Svetlana P SP   Grigorchuk Valeria P VP   Kaune Moritz M   Amsberg Gunhild von GV   Dyshlovoy Sergey A SA  

Marine drugs 20190825 9

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-D  ...[more]

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