Plitidepsin

• CAS: 137219-37-5
• Catalog Number: ACM137219375
• Category: Inhibitors
• Molecular Weight: 1110.34
• Molecular Formula: C57H87N7O15
• Description: Plitidepsin is a cyclic depsipeptide isolated from the marine tunicate Aplidium albicans. Plitidepsin displays a broad spectrum of antitumor activities, 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.
• Synonyms: aplidine; dehydrodemnin B. US brand name: Aplidin
• IUPAC Name: (S)-N-((R)-1-(((3S,6R,7S,10R,11S,15S,17S,20S,25aS)-10-((S)-sec-butyl)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15]dioxa[4,7,10,20]tetraazacyclotricosin-7-yl)amino)-4-methyl-1-oxopentan-2-yl)-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
• Canonical SMILES: CC[C@@H]([C@@H]1[C@@H](O)CC(O[C@@H](C(C)C)C([C@H](C)C(N[C@@H](CC(C)C)C(N2CCC[C@H]2C(N(C)[C@@H](CC3=CC=C(OC)C=C3)C(O[C@H](C)[C@H](NC([C@H](N(C([C@@H]4CCCN4C(C(C)=O)=O)=O)C)CC(C)C)=O)C(N1)=O)=O)=O)=O)=O)=O)=O)C
• 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
• InChI Key: UUSZLLQJYRSZIS-LXNNNBEUSA-N
• Solubility: Soluble in DMSO, not soluble in water
• Appearance: Solid powder
• Shelf Life: >5 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Biological Target: Plitidepsin is a cyclic depsipeptide that inhibits elongation factor 1-a and induces G1 arrest and G2 blockade.
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 61.66; H, 7.90; N, 8.83; O, 21.61
• Exact Mass: 1109.62602
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: It was investigated, in vitro, whether aplidine could affect endothelial cell functions relevant to angiogenesis. Aplidine inhibited the proliferation of endothelial cells (Figure 4). The antiproliferative effect of aplidine was observed when proliferation was stimulated by both VEGF and FGF-2. Some inhibitory effect was observed after 1 h exposure to the compound, with IC50 of 8.1 and 5.7 nm for VEGF and FGF-2, respectively. Exposure to aplidine for longer times (24-72 h) increased the cytotoxic effect of the compound (Figure 4). Aplidine also affected endothelial cell motility and invasiveness, assayed in the Boyden chamber, using supernatant of NIH-3T3 cells as the attractant. Pretreatment with aplidine for 1 h resulted in a dose-dependent inhibition of cell migration, with an IC50 of 5.5 nm for chemotaxis and 0.9 nm for invasiveness (Figure 5). The same results were obtained when aplidine was added to the lower compartment of the chemotaxis chamber (not shown). Aplidine also inhibited the motility and invasive response of endothelial cells to VEGF and FGF-2 (for chemotaxis, IC50 was 9.5 and 11.6 nm; for chemoinvasion, IC50 was 1.8 and 0.5 nm for VEGF and FGF-2, respectively). These findings that aplidine blocked endothelial cell proliferation, migration, invasion and cord formation in vitro suggest that the compound acts at multiple levels of the angiogenic cascade.; Reference: Br J Cancer. 2004 Jun 14; 90(12): 2418-2424. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2409535/
• In Vivo Activity: The antiangiogenic activity of aplidine was investigated in the chick CAM assay, in vivo, a useful model to investigate the effect of compounds on both basal angiogenesis and angiogenesis induced by an exogenous stimulus (Ribatti et al, 2001). Aplidine, added to the CAM, affected the basal growth of vessels, inhibiting the number of blood vessels in 80% of the treated embryos (Figure 1). Aplidine also affected angiogenesis induced by exogenous angiogenic factors added to the CAMs. Vascular endothelial growth factor or FGF-2 induced the growth of numerous allantoic vessels converging like spokes toward the sponge (Figure 2A). Aplidine (10 nm) significantly reduced the angiogenic response induced by VEGF and, at a lower extent, by FGF-2 (Figures 1 and 2B). It was next investigated whether aplidine also inhibited tumour angiogenesis induced in the CAM by tumours. The human ovarian carcinoma 1A9 and its VEGF overexpressing clone 1A9-VS4 were injected subcutaneously in nude mice. The addition of aplidine caused a significant (P⩽0.001) reduction in the angiogenic response induced by the tumour specimens (number of vessels was 20±4 and 11±3 for 1A9-VS4 and 1A9, respectively, Figure 3B). These findings indicate that aplidine prevented angiogenesis in vivo, affecting both physiologic, spontaneous angiogenesis of the embryo, angiogenesis induced by exogenous stimuli (VEGF and FGF-2) and tumour angiogenesis; Reference: Br J Cancer. 2004 Jun 14; 90(12): 2418-2424. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2409535/
• Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
• Source: Mediterranean tunicate Aplidium albicans
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).

Custom Q&A

What is the molecular formula of Plitidepsin?

The molecular formula of Plitidepsin is C57H87N7O15.

Is Plitidepsin a synthetic or natural compound?

Plitidepsin is a natural compound originally isolated from the Mediterranean tunicate Aplidium albicans.

What are the synonyms of Plitidepsin?

The synonyms of Plitidepsin are Aplidine, aplidin, 137219-37-5, and Dehydrodidemnin B.

What is the molecular weight of Plitidepsin?

The molecular weight of Plitidepsin is 1110.3 g/mol.

What is the IUPAC name of Plitidepsin?

The IUPAC name of Plitidepsin is (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.

What is the InChIKey of Plitidepsin?

The InChIKey of Plitidepsin is UUSZLLQJYRSZIS-LXNNNBEUSA-N.

What is the CAS number of Plitidepsin?

The CAS number of Plitidepsin is 137219-37-5.

What is the UNII of Plitidepsin?

The UNII of Plitidepsin is Y76ID234HW.

What is the ChEMBL ID of Plitidepsin?

The ChEMBL ID of Plitidepsin is CHEMBL451930.

Is Plitidepsin used as an antineoplastic agent?

Yes, Plitidepsin is used as an antineoplastic agent, meaning it is used to treat cancer.