Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues
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Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues. / Zhidkov, Maxim E; Smirnova, Polina A; Tryapkin, Oleg A; Kantemirov, Alexey V; Khudyakova, Yuliya V; Malyarenko, Olesya S; Ermakova, Svetlana P; Grigorchuk, Valeria P; Kaune, Moritz; Amsberg, Gunhild von; Dyshlovoy, Sergey A.
In: MAR DRUGS, Vol. 17, No. 9, 25.08.2019.Research output: SCORING: Contribution to journal › SCORING: Journal article › Research › peer-review
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TY - JOUR
T1 - Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues
AU - Zhidkov, Maxim E
AU - Smirnova, Polina A
AU - Tryapkin, Oleg A
AU - Kantemirov, Alexey V
AU - Khudyakova, Yuliya V
AU - Malyarenko, Olesya S
AU - Ermakova, Svetlana P
AU - Grigorchuk, Valeria P
AU - Kaune, Moritz
AU - Amsberg, Gunhild von
AU - Dyshlovoy, Sergey A
PY - 2019/8/25
Y1 - 2019/8/25
N2 - 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.
AB - 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.
U2 - 10.3390/md17090496
DO - 10.3390/md17090496
M3 - SCORING: Journal article
C2 - 31450717
VL - 17
JO - MAR DRUGS
JF - MAR DRUGS
SN - 1660-3397
IS - 9
ER -