567715 N-SMase Inhibitor, GW4869 - CAS 6823-69-4 - Calbiochem

567715
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Key Specifications Table

Empirical FormulaCAS #
C₃₀H₂₈N₆O₂ • 2HCl 6823-69-4

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567715-1MG
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      Description
      OverviewA cell-permeable, symmetrical dihydroimidazolo-amide compound that acts as a potent, specific, non-competitive inhibitor of N-SMase (neutral sphingomyelinase) [IC50 = ~ 1 µM, rat brain; Km for sphingomyelin ~13 µM]. Does not inhibit human A-SMase (acid sphingomyelinase) even at 150 µM. Weakly inhibits the activities of bovine protein phosphatase 2A and mammalian lyso-PAF PLC, while no inhibition is observed for bacterial phosphatidylcholine-specific PLC. Reported to offer complete protection against TNF-α or diamine-induced cell death in MCF7 breast cancer cells at 20 µM. Does not modify the intracellular glutathione levels or interfere with TNF-α or diamine-mediated signaling effects.
      Catalogue Number567715
      Brand Family Calbiochem®
      SynonymsSphingomyelinase, Neutral, Inhibitor GW4869, GW69A, GW554869A
      References
      ReferencesMarchesini, N., et al. 2003. J. Biol. Chem. In press.
      Luberto, C., et al. 2002. J. Biol. Chem. 277, 41128
      Okamoto, Y., et al. 2002. FEBS Lett. 530, 140.
      Product Information
      CAS number6823-69-4
      ATP CompetitiveN
      FormPale yellow solid
      Hill FormulaC₃₀H₂₈N₆O₂ • 2HCl
      Chemical formulaC₃₀H₂₈N₆O₂ • 2HCl
      Hygroscopic Hygroscopic
      ReversibleN
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      ApplicationN-SMase Inhibitor, GW4869 - CAS 6823-69-4, is a cell-permeable, potent, specific, non-competitive inhibitor of N-SMase (IC50 = ~ 1 µM, rat brain) Does not inhibit human acid SMase even at 150 µM.
      Biological Information
      Primary TargetN-Smase rat brain
      Primary Target IC<sub>50</sub>1 µM rat brain N-SMase (neutral sphingomyelinase); Km for sphingomyelin ~13 µM
      Purity≥90% by NMR
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Blue Ice Only
      Toxicity Standard Handling
      Storage -20°C
      Protect from Light Protect from light
      Hygroscopic Hygroscopic
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      N-SMase Inhibitor, GW4869 - CAS 6823-69-4 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      N-SMase Inhibitor, GW4869 - CAS 6823-69-4 - Calbiochem Certificates of Analysis

      TitleLot Number
      567715

      References

      Reference overview
      Marchesini, N., et al. 2003. J. Biol. Chem. In press.
      Luberto, C., et al. 2002. J. Biol. Chem. 277, 41128
      Okamoto, Y., et al. 2002. FEBS Lett. 530, 140.
      Data Sheet

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision11-April-2013 JSW
      SynonymsSphingomyelinase, Neutral, Inhibitor GW4869, GW69A, GW554869A
      DescriptionA cell permeable, symmetrical dihydroimidazolo-amide that acts as a potent, specific, and non-competitive inhibitor of neutral sphingomyelinase (N-SMase) (IC50 = 1 µM, rat brain N-SMase). Reported to inhibit tumor necrosis factor α (TNF-α) induced sphingomyelin hydrolysis (100% inhibition at 20 µM) and TNF-α-induced cell death in MCF7 cells. Does not interfere with other TNF-α-mediated signaling events, such as de novo ceramide synthesis and NF-κB activation and nuclear translocation. Exhibits no effect on cellular glutathione levels that are normally reduced in response to TNF-α. Does not inhibit acid sphingomyelinase (A-SMase) or bacterial phosphatidylcholine-specific phospholipase C (PC-PLC). Shown to weakly inhibit bovine protein phosphatase 2A (PP2A) and human lyso-PAF PLC, an enzyme that hydrolyzes sphingomyelin in vitro.
      FormPale yellow solid
      Intert gas (Yes/No) Packaged under inert gas
      CAS number6823-69-4
      Chemical formulaC₃₀H₂₈N₆O₂ • 2HCl
      Structure formulaStructure formula
      Purity≥90% by NMR
      SolubilityDMSO (200 µg/ml)
      Storage -20°C
      Hygroscopic
      Protect from light
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Toxicity Standard Handling
      ReferencesMarchesini, N., et al. 2003. J. Biol. Chem. In press.
      Luberto, C., et al. 2002. J. Biol. Chem. 277, 41128
      Okamoto, Y., et al. 2002. FEBS Lett. 530, 140.