Plitidepsin

Category	SARS-CoV
CAS	137219-37-5
Description	Plitidepsin is a cyclic depsipeptide isolated from the marine tunicate Aplidium albicans. Plitidepsin shows potent anticancer activity against a large variety of cultured human cancer cells, inducing apoptosis by triggering mitochondrial cytochrome c release, initiating the Fas/DC95, JNK pathway and activating caspase 3 activation. This agent also inhibits elongation factor 1-a, thereby interfering with protein synthesis, and induces G1 arrest and G2 blockade, thereby inhibiting tumor cell growth.

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Product Information

Synonyms	aplidin; aplidine; plitidepsin; dehydrodidemnin B
IUPAC Name	(2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
Molecular Weight	1110.34
Molecular Formula	C57H87N7O15
Canonical SMILES	CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)C3CCCN3C(=O)C(=O)C)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
InChI	InChI=1S/C57H87N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-34,36,39-44,46-47,49,66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33?,34-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1
InChIKey	UUSZLLQJYRSZIS-UJCFUGBQSA-N
Melting Point	152-160°C
Purity	>98%
Density	1.24±0.1 g/cm3(Predicted)
Solubility	Soluble in DMSO
Appearance	Solid Powder
Storage	Store at -20°C
Complexity	2200
Exact Mass	1109.62601509
Index Of Refraction	1.567
In Vitro	Plitidepsin (20 nM; 1 h) induces a dose-dependent decrease in VEGF secretion in MOLT-4 cells. Plitidepsin (20 nM; 1 h) does not result in significant inhibition of VEGF-R1 mRNA in normal endothelial cells, which do express VEGFR-1 but do not secrete VEGF. Plitidepsin inhibits SARS-CoV-2 with an IC90 of 1.76 nM. In hACE2-293T cells, Plitidepsin exhibits anti-SARS-CoV-2 activity with an IC90 of 0.88 nM. In an established model of human pneumocyte-like cells, Plitidepsin inhibits SARS-CoV-2 replication with an IC90 of 3.14 nM and a selectivity index of 40.4.
In Vivo	Plitidepsin (20 nM; 1 h) induces a dose-dependent decrease in VEGF secretion in MOLT-4 cells.
PSA	295.21000
Target	DNA/RNA Synthesis; SARS-CoV
XLogP3-AA	5.7