About: Coibamide A

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Coibamide A is an antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium. Testing of coibamide A in the National Cancer Institute in vitro 60 human tumor cell line panel (NCI-60) revealed potent anti-proliferative activity and a unique selectivity profile. Similarities between coibamide A- and apratoxin A-induced changes in cell morphology, decreases in VEGFR2 expression and macroautophagy signaling in HUVECs raise the possibility that both cyanobacterial natural products share a common mechanism of action. Wild-type mouse embryonic fibroblasts were more vulnerable to coibamide A than cells lacking autophagy-related protein 5 (Atg5) that suggest coibamide A as a compound with characteristics that may utilize autophagy for pro-death signaling.

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  • Coibamide A is an antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium. Testing of coibamide A in the National Cancer Institute in vitro 60 human tumor cell line panel (NCI-60) revealed potent anti-proliferative activity and a unique selectivity profile. Similarities between coibamide A- and apratoxin A-induced changes in cell morphology, decreases in VEGFR2 expression and macroautophagy signaling in HUVECs raise the possibility that both cyanobacterial natural products share a common mechanism of action. Wild-type mouse embryonic fibroblasts were more vulnerable to coibamide A than cells lacking autophagy-related protein 5 (Atg5) that suggest coibamide A as a compound with characteristics that may utilize autophagy for pro-death signaling. Solid-phase total syntheses of highly methylated cyclic azacoibamide A and its O-desmethyl analog were achieved to improve pharmacokinetic properties of coibamide A. (en)
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  • N-{(2S)-2-[(N,N-Dimethyl-(L)-valyl)oxy]-3-methylbutanoyl}-N,O-dimethyl-(L)-seryl-N-[(3S,6S,9S,12S,15S,18S,21S,22R)-15-[(2S)-2-butanyl]-9-isobutyl-6-(4-methoxybenzyl)-18-(methoxymethyl)-3,4,10,12,16,19,22-heptamethyl-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-21-yl]-N,N2-dimethyl-(L)-leucinamide (en)
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  • Coibamide A.svg (en)
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  • N-{-2-[oxy]-3-methylbutanoyl}-N,O-dimethyl-(L)-seryl-N-[-15-[-2-butanyl]-9-isobutyl-6--18--3,4,10,12,16,19,22-heptamethyl-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-21-yl]-N,N2-dimethyl-(L)-leucinamide (en)
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  • Coibamide A is an antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium. Testing of coibamide A in the National Cancer Institute in vitro 60 human tumor cell line panel (NCI-60) revealed potent anti-proliferative activity and a unique selectivity profile. Similarities between coibamide A- and apratoxin A-induced changes in cell morphology, decreases in VEGFR2 expression and macroautophagy signaling in HUVECs raise the possibility that both cyanobacterial natural products share a common mechanism of action. Wild-type mouse embryonic fibroblasts were more vulnerable to coibamide A than cells lacking autophagy-related protein 5 (Atg5) that suggest coibamide A as a compound with characteristics that may utilize autophagy for pro-death signaling. (en)
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  • Coibamide A (en)
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