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Category Enzyme inhibitors
Catalog number BBF-04651
CAS 137219-37-5
Molecular Weight 1110.34
Molecular Formula C57H87N7O15
Purity >98%

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BBF-04651 1 mg $1099 In stock

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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.


Synonyms aplidin; aplidine; plitidepsin; dehydrodidemnin B
Storage Store at -20°C
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
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


Appearance Solid Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Melting Point 152-160°C
Density 1.24±0.1 g/cm3(Predicted)
Solubility Soluble in DMSO

Reference Reading

1.Cellular Uptake and Cytotoxic Effect of Epidermal Growth Factor Receptor Targeted and Plitidepsin Loaded Co-Polymeric Polymersomes on Colorectal Cancer Cell Lines.
Goñi-de-Cerio F, Thevenot J, Oliveira H, Pérez-Andrés E, Berra E, Masa M, Suárez-Merino B, Lecommandoux S, Heredia P. J Biomed Nanotechnol. 2015 Nov;11(11):2034-49.
Encapsulating chemotherapy drugs in targeted nanodelivery systems is one of the most promising approaches to tackle cancer disease, avoiding side effects of common treatment. In the last decade, several nanocarriers with different nature have been tested, but polypeptide-based copolymers have attracted considerable attention for their biocompatibility, controlled and slow biodegradability as well as their low toxicity. In this work, we synthesized, characterized and evaluated poly(trimethylene carbonate)-bock-poly(L-glutamic acid) derived polymersomes, targeted to epidermal growth factor receptor (EGFR), loaded with plitidepsin and ultimately tested in HT29 and LS174T colorectal cancer cell lines for specificity and efficacy. Furthermore, morphology, physico-chemical properties and plitidepsin loading were carefully investigated. A thorough in vitro cytotoxicity analysis of the unloaded polymersomes was carried out for biocompatibility check, studying viability, cell membrane asymmetry and reactive oxygen species levels.
2.Phase I-II study of plitidepsin and dacarbazine as first-line therapy for advanced melanoma.
Plummer R1, Lorigan P, Brown E, Zaucha R, Moiseyenko V, Demidov L, Soriano V, Chmielowska E, Andrés R, Kudryavtseva G, Kahatt C, Szyldergemajn S, Extremera S, de Miguel B, Cullell-Young M, Calvert H. Br J Cancer. 2013 Sep 17;109(6):1451-9. doi: 10.1038/bjc.2013.477. Epub 2013 Aug 29.
BACKGROUND: This phase I-II trial compared plitidepsin 1-h infusion alone or combined with dacarbazine (DTIC) 1-h infusion as front-line therapy for advanced melanoma.
3.Nano-encapsulation of plitidepsin: in vivo pharmacokinetics, biodistribution, and efficacy in a renal xenograft tumor model.
Oliveira H1, Thevenot J, Garanger E, Ibarboure E, Calvo P, Aviles P, Guillen MJ, Lecommandoux S. Pharm Res. 2014 Apr;31(4):983-91. doi: 10.1007/s11095-013-1220-3. Epub 2013 Nov 28.
PURPOSE: Plitidepsin is an antineoplasic currently in clinical evaluation in a phase III trial in multiple myeloma (ADMYRE). Presently, the hydrophobic drug plitidepsin is formulated using Cremophor®, an adjuvant associated with unwanted hypersensitivity reactions. In search of alternatives, we developed and tested two nanoparticle-based formulations of plitidepsin, aiming to modify/improve drug biodistribution and efficacy.
4.Evaluation of plitidepsin in patients with primary myelofibrosis and post polycythemia vera/essential thrombocythemia myelofibrosis: results of preclinical studies and a phase II clinical trial.
Pardanani A1, Tefferi A1, Guglielmelli P2, Bogani C2, Bartalucci N2, Rodríguez J3, Extremera S3, Pérez I3, Alfaro V3, Vannucchi AM2. Blood Cancer J. 2015 Mar 13;5:e286. doi: 10.1038/bcj.2015.5.
Previous data established that plitidepsin, a cyclic depsipeptide, exerted activity in a mouse model of myelofibrosis (MF). New preclinical experiments reported herein found that low nanomolar plitidepsin concentrations potently inhibited the proliferation of JAK2V617F-mutated cell lines and reduced colony formation by CD34+ cells of individuals with MF, at least in part through modulation of p27 levels. Cells of MF patients had significantly reduced p27 content, that were modestly increased upon plitidepsin exposure. On these premise, an exploratory phase II trial evaluated plitidepsin 5 mg/m(2) 3-h intravenous infusion administered on days 1 and 15 every 4 weeks (q4wk). Response rate (RR) according to the International Working Group for Myelofibrosis Research and Treatment consensus criteria was 9.1% (95% CI, 0.2-41.3%) in 11 evaluable patients during the first trial stage. The single responder achieved a red cell transfusion independence and stable disease was reported in nine additional patients (81.

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