WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 509120
Description: YM201636 is an inhibitor of retroviral budding and PIKfyve-catalyzed PtdIns(3,5)P2 synthesis, and can also halt glucose entry by insulin in adipocytes. YM201636 almost completely inhibited basal and insulin-activated 2-deoxyglucose uptake at doses as low as 160 nM, with IC(50)=54+/-4 nM for the net insulin response. Insulin-induced GLUT4 translocation was partially inhibited at substantially higher doses, comparable to those required for inhibition of insulin-induced phosphorylation of Akt/PKB. In addition to PIKfyve, YM201636 also completely inhibited insulin-dependent activation of class IA PI 3-kinase.
MedKoo Cat#: 509120
Chemical Formula: C25H21N7O3
Exact Mass: 467.17059
Molecular Weight: 467.48
Elemental Analysis: C, 64.23; H, 4.53; N, 20.97; O, 10.27
Synonym: YM201636 YM-201636 YM 201636.
IUPAC/Chemical Name: 6-amino-N-(3-(4-(4-morpholinyl)pyrido(3',2'-4,5)furo(3,2-d)pyrimidin-2-yl)phenyl)-3-pyridinecarboxamide
InChi Key: YBPIBGNBHHGLEB-UHFFFAOYSA-N
InChi Code: InChI=1S/C25H21N7O3/c26-19-7-6-16(14-28-19)24(33)29-17-4-1-3-15(13-17)22-30-20-18-5-2-8-27-25(18)35-21(20)23(31-22)32-9-11-34-12-10-32/h1-8,13-14H,9-12H2,(H2,26,28)(H,29,33)
SMILES Code: O=C(C1=CC=C(N)N=C1)NC2=CC=CC(C3=NC(N4CCOCC4)=C(OC5=NC=CC=C56)C6=N3)=C2
Appearance: White to off-white solid powder.
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: 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.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 467.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Mauthe M, Yu W, Krut O, KrÃ¶nke M, GÃ¶tz F, Robenek H, Proikas-Cezanne T. WIPI-1 Positive Autophagosome-Like Vesicles Entrap Pathogenic Staphylococcus aureus for Lysosomal Degradation. Int J Cell Biol. 2012;2012:179207. Epub 2012 Jul 9. PubMed PMID: 22829830; PubMed Central PMCID: PMC3399381.
2: Sbrissa D, Ikonomov OC, Filios C, Delvecchio K, Shisheva A. Functional dissociation between PIKfyve-synthesized PtdIns5P and PtdIns(3,5)P2 by means of the PIKfyve inhibitor YM201636. Am J Physiol Cell Physiol. 2012 May 23. [Epub ahead of print] PubMed PMID: 22621786.
3: Seebohm G, Neumann S, Theiss C, Novkovic T, Hill EV, TavarÃ© JM, Lang F, Hollmann M, Manahan-Vaughan D, Strutz-Seebohm N. Identification of a novel signaling pathway and its relevance for GluA1 recycling. PLoS One. 2012;7(3):e33889. Epub 2012 Mar 21. PubMed PMID: 22470488; PubMed Central PMCID: PMC3309939.
4: Dukes JD, Whitley P, Chalmers AD. The PIKfyve inhibitor YM201636 blocks the continuous recycling of the tight junction proteins claudin-1 and claudin-2 in MDCK cells. PLoS One. 2012;7(3):e28659. Epub 2012 Mar 1. PubMed PMID: 22396724; PubMed Central PMCID: PMC3291620.
5: Vaccari I, Dina G, TronchÃ¨re H, Kaufman E, Chicanne G, Cerri F, Wrabetz L, Payrastre B, Quattrini A, Weisman LS, Meisler MH, Bolino A. Genetic interaction between MTMR2 and FIG4 phospholipid phosphatases involved in Charcot-Marie-Tooth neuropathies. PLoS Genet. 2011 Oct;7(10):e1002319. Epub 2011 Oct 20. PubMed PMID: 22028665; PubMed Central PMCID: PMC3197679.
6: Dupuis-Coronas S, Lagarrigue F, Ramel D, Chicanne G, Saland E, Gaits-Iacovoni F, Payrastre B, TronchÃ¨re H. The nucleophosmin-anaplastic lymphoma kinase oncogene interacts, activates, and uses the kinase PIKfyve to increase invasiveness. J Biol Chem. 2011 Sep 16;286(37):32105-14. Epub 2011 Jul 7. PubMed PMID: 21737449; PubMed Central PMCID: PMC3173219.
7: Fernandes F, Chen K, Ehrlich LS, Jin J, Chen MH, Medina GN, Symons M, Montelaro R, Donaldson J, Tjandra N, Carter CA. Phosphoinositides direct equine infectious anemia virus gag trafficking and release. Traffic. 2011 Apr;12(4):438-51. doi: 10.1111/j.1600-0854.2010.01153.x. Epub 2011 Feb 1. PubMed PMID: 21176037; PubMed Central PMCID: PMC3064743.
8: Kerr MC, Wang JT, Castro NA, Hamilton NA, Town L, Brown DL, Meunier FA, Brown NF, Stow JL, Teasdale RD. Inhibition of the PtdIns(5) kinase PIKfyve disrupts intracellular replication of Salmonella. EMBO J. 2010 Apr 21;29(8):1331-47. Epub 2010 Mar 18. PubMed PMID: 20300065; PubMed Central PMCID: PMC2868569.
9: Ikonomov OC, Sbrissa D, Shisheva A. YM201636, an inhibitor of retroviral budding and PIKfyve-catalyzed PtdIns(3,5)P2 synthesis, halts glucose entry by insulin in adipocytes. Biochem Biophys Res Commun. 2009 May 8;382(3):566-70. Epub 2009 Mar 14. PubMed PMID: 19289105.
10: Jefferies HB, Cooke FT, Jat P, Boucheron C, Koizumi T, Hayakawa M, Kaizawa H, Ohishi T, Workman P, Waterfield MD, Parker PJ. A selective PIKfyve inhibitor blocks PtdIns(3,5)P(2) production and disrupts endomembrane transport and retroviral budding. EMBO Rep. 2008 Feb;9(2):164-70. Epub 2008 Jan 11. PubMed PMID: 18188180; PubMed Central PMCID: PMC2246419.