Plinabulin

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WARNING: This product is for research use only, not for human or veterinary use.

Description:Plinabulin is a VDA of novel structure in having been derived from a marine microbial source, as opposed to terrestrial sources for other VDAs. Plinabulin binds to the colchicine binding site of b-tubulin preventing polymerization and disrupting the cytoplasmic microtubule network. Plinabulin has been shown to produce anti-tumor activity in animal models as a single agent and synergistically with other chemotherapy agents including taxanes. Overall, preclinical studies indicated plinabulin had a favorable safety and activity profile leading to the initiation of clinical trials. Favorable data from early clinical studies lead to the initiation of a Phase 2 clinical trial program..

Price and Availability

Plinabulin, purity > 98%, is in stock. Note: the estimated shipping out time for order > 5g may be 2 weeks.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 202040Name: PlinabulinCAS#: 714272-27-2Chemical Formula: C19H20N4O2Exact Mass: 336.15863Molecular Weight: 336.39Elemental Analysis:C, 67.84; H, 5.99; N, 16.66; O, 9.51

Synonym:NPI 2358; NPI2358; NPI-2358; Plinabulin

IUPAC/Chemical Name:(3E,6E)-3-benzylidene-6-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)piperazine-2,5-dione

InChi Key:UNRCMCRRFYFGFX-AOEKMSOUSA-N

InChi Code:InChI=1S/C19H20N4O2/c1-19(2,3)16-13(20-11-21-16)10-15-18(25)22-14(17(24)23-15)9-12-7-5-4-6-8-12/h4-11H,1-3H3,(H,20,21)(H,22,25)(H,23,24)/b14-9+,15-10+

SMILES Code:O=C(/C(NC/1=O)=CC2=CC=CC=C2)NC1=CC3=C(C(C)(C)C)NC=N3

Technical Data

Additional Information

References

1: Yakushiji F, Tanaka H, Muguruma K, Iwahashi T,Yamazaki Y, Hayashi Y. Prodrug study of plinabulin using a clickstrategy focused on the effects of a replaceable water-solubilizingmoiety. Chem Pharm Bull (Tokyo). 2012;60(7):877-81. PubMed PMID:22790821.

2: Yakushiji F, Tanaka H, Muguruma K, Iwahashi T, Yamazaki Y, Hayashi Y.Water-soluble prodrug of antimicrotubule agent plinabulin: effectivestrategy with click chemistry. Chemistry. 2011 Nov 4;17(45):12587-90.doi: 10.1002/chem.201102293. Epub 2011 Sep 29. PubMed PMID: 21956869.

3: Bertelsen LB, Shen YY, Nielsen T, Stødkilde-Jørgensen H, Lloyd GK,Siemann DW, Horsman MR. Vascular effects of plinabulin (NPI-2358) andthe influence on tumour response when given alone or combined withradiation. Int J Radiat Biol. 2011 Nov;87(11):1126-34. doi:10.3109/09553002.2011.605418. PubMed PMID: 21815749; PubMed CentralPMCID: PMC3509771.

4: Singh AV, Bandi M, Raje N, Richardson P, Palladino MA, Chauhan D,Anderson KC. A novel vascular disrupting agent plinabulin triggersJNK-mediated apoptosis and inhibits angiogenesis in multiple myelomacells. Blood. 2011 May 26;117(21):5692-700. doi:10.1182/blood-2010-12-323857. Epub 2011 Mar 31. PubMed PMID: 21454451;PubMed Central PMCID: PMC3110026.

5: Millward M, Mainwaring P, Mita A, Federico K, Lloyd GK, Reddinger N,Nawrocki S, Mita M, Spear MA. Phase 1 study of the novel vasculardisrupting agent plinabulin (NPI-2358) and docetaxel. Invest New Drugs.2012 Jun;30(3):1065-73. doi: 10.1007/s10637-011-9642-4. Epub 2011 Feb16. PubMed PMID: 21327495.

6: Mita MM, Spear MA, Yee LK, Mita AC, Heath EI, Papadopoulos KP,Federico KC, Reich SD, Romero O, Malburg L, Pilat M, Lloyd GK, NeuteboomST, Cropp G, Ashton E, LoRusso PM. Phase 1 first-in-human trial of thevascular disrupting agent plinabulin(NPI-2358) in patients with solidtumors or lymphomas. Clin Cancer Res. 2010 Dec 1;16(23):5892-9. doi:10.1158/1078-0432.CCR-10-1096. PubMed PMID: 21138873.

7: Yamazaki Y, Kido Y, Hidaka K, Yasui H, Kiso Y, Yakushiji F, HayashiY. Tubulin photoaffinity labeling study with a plinabulin chemical probepossessing a biotin tag at the oxazole. Bioorg Med Chem. 2011 Jan1;19(1):595-602. doi: 10.1016/j.bmc.2010.10.055. Epub 2010 Oct 31.PubMed PMID: 21106379.

8: Yamazaki Y, Sumikura M, Hidaka K, Yasui H, Kiso Y, Yakushiji F,Hayashi Y. Anti-microtubule "plinabulin" chemical probe KPU-244-B3labeled both alpha- and beta-tubulin. Bioorg Med Chem. 2010 May1;18(9):3169-74. doi: 10.1016/j.bmc.2010.03.037. Epub 2010 Mar 23.PubMed PMID: 20395148.