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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

GW 4869

Cayman Chemical Item Number 13127

(CAS 6823-69-4)

GW 4869 (CAS 6823-69-4)

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Description

Neutral sphingomyelinases mediate the release of ceramide from sphingomyelin in cellular membranes and can be activated by certain stresses. Ceramide can act as a signaling molecule in its own right, or it can be further processed to generate sphingosine (and sphingosine-1-phosphate). GW 4869 is a cell-permeable non-competitive inhibitor of neutral sphingomyelinases (IC50 = 1 μM), but does not affect acid sphingomyelinase activity.1 It inhibits TNF-α-mediated sphingomyelin hydrolysis (100% inhibition at 20 μM) 1 and TNF-α-induced cell death in MCF7 cells without interfering with activation of NF-κB or glutathione depletion in response to TNF.1,2 GW 4869 also reduces the inhibitory effect of oxidized phospholipid products on lipopolysaccharides-mediated induction of interleukin-8 in human aortic endothelial cells 3 and prevents hypoxia-induced pulmonary vasoconstriction in rats in vivo.4

1 Luberto, C., Hassler, D.F., Signorelli, P., et al. Inhibition of tumor necrosis factor-induced cell death in MCF7 by a novel inhibitor of neutral sphingomyelinase. J Biol Chem 277(43) 41128-41139 (2002).

2 Marchesini, N., Luberto, C., and Hannun, Y.A. Biochemical properties of mammalian neutral sphingomyelinase2 and its role in sphingolipid metabolism. J Biol Chem 278(16) 13775-13783 (2003).

3 Walton, K.A., Gugiu, B.G., Thomas, M., et al. A role for neutral sphingomyelinase activation in the inhibition of LPS action by phospholipid oxidation products. J Lipid Res 47 1967-1974 (2006).

4 Cogolludo, A., Moreno, L., Frazziano, G., et al. Activation of neutral spingomyelinase is involved in acute hypoxic pulmonary vasoconstriction. Cardiovasc Res 82 296-302 (2009).

Formal Name 3,​3'-​(1,​4-​phenylene)bis[N-​[4-​(4,​5-​dihydro-​1H-​imidazol-​2-​yl)phenyl]-​hydrochloride-​2-​propenamide
CAS Number 6823-69-4
Molecular Formula C30H28N6O2 · 2HCl
Formula Weight 577.5
Formulation A crystalline solid
Purity ≥90%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(/C=C\c1ccc(cc1)​\C=C/C(=O)​Nc1ccc(cc1)​C1=NCCN1)​Nc1ccc(cc1)​C1=NCCN1

Background Reading

Marchesini, N., Luberto, C., and Hannun, Y.A. Biochemical properties of mammalian neutral sphingomyelinase2 and its role in sphingolipid metabolism. J Biol Chem 278(16) 13775-13783 (2003).

Walton, K.A., Gugiu, B.G., Thomas, M., et al. A role for neutral sphingomyelinase activation in the inhibition of LPS action by phospholipid oxidation products. J Lipid Res 47 1967-1974 (2006).

Cogolludo, A., Moreno, L., Frazziano, G., et al. Activation of neutral spingomyelinase is involved in acute hypoxic pulmonary vasoconstriction. Cardiovasc Res 82 296-302 (2009).

Luberto, C., Hassler, D.F., Signorelli, P., et al. Inhibition of tumor necrosis factor-induced cell death in MCF7 by a novel inhibitor of neutral sphingomyelinase. J Biol Chem 277(43) 41128-41139 (2002).

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GW 4869 is available in the following screening library:

Size Price Quantity Subtotal
500 µg $43.00 $0.00
1 mg $82.00 $0.00
5 mg $344.00 $0.00
10 mg $602.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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