567715
N-SMase Inhibitor, GW4869
The N-SMase Inhibitor, GW4869, also referenced under CAS 6823-69-4, controls the biological activity of N-SMase. This small molecule/inhibitor is primarily used for Cell Signaling applications.
Synonym(s):
N-SMase Inhibitor, GW4869, Sphingomyelinase, Neutral, Inhibitor GW4869, GW69A, GW554869A
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Quality Level
assay
≥90% (NMR)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, desiccated (hygroscopic), protect from light
color
pale yellow
solubility
DMSO: 200 μg/mL
shipped in
wet ice
storage temp.
−20°C
InChI
1S/C30H28N6O2.2ClH/c37-27(35-25-11-7-23(8-12-25)29-31-17-18-32-29)15-5-21-1-2-22(4-3-21)6-16-28(38)36-26-13-9-24(10-14-26)30-33-19-20-34-30;;/h1-16H,17-20H2,(H,31,32)(H,33,34)(H,35,37)(H,36,38);2*1H/b15-5+,16-6+;;
InChI key
NSFKAZDTKIKLKT-CLEIDKRQSA-N
General description
A 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.
A 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.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
N-Smase rat brain
N-Smase rat brain
Product does not compete with ATP.
Reversible: no
Target IC50: 1 µM rat brain N-SMase (neutral sphingomyelinase); Km for sphingomyelin ~13 µM
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
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.
Luberto, C., et al. 2002. J. Biol. Chem.277, 41128
Okamoto, Y., et al. 2002. FEBS Lett.530, 140.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| 567715-1MG | 07790788055608 |