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

567715
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      Overview

      Replacement Information

      Key Specifications Table

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

      Pricing & Availability

      Catalog Number AvailabilityPackaging Qty/Pack Price Quantity
      567715-1MG
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          Plastic ampoule 1 mg
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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
          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.