Inhibitor of neutral sphingomyelinase
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GW 4869 (hydrochloride hydrate)

Item No. 13127

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,3'-(1,4-phenylene)bis[N-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-dihydrochloride-2-propenamide
CAS Number
6823-69-4
Molecular Formula
C30H28N6O2 • 2HCl [XH2O]
Formula Weight
577.5
Purity
≥90%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 0.2 mg/ml
λmax
346 nm
SMILES
O=C(NC1=CC=C(C2=NCCN2)C=C1)/C=C/C3=CC=C(/C=C/C(NC4=CC=C(C5=NCCN5)C=C4)=O)C=C3.Cl.Cl.O
InChi Code
InChI=1S/C30H28N6O2.2ClH.H2O/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;1H2/b15-5+,16-6+;;;
InChi Key
DKFSVQGRETYFBG-ZAKYHKHWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $39

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    1 mg

    $74

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    5 mg

    $154

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    10 mg

    $270

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    Product 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 an inhibitor of neutral sphingomyelinase (IC50 = 1 μM).1 It is selective for neutral sphingomyelinase over acid sphingomyelinase at concentrations up to 150 μM as well as B. cereus PC-PLC, human lyso-PAF PLC, and bovine PP2A at 10 μM. GW 4869 inhibits TNF-α-induced sphingomyelin hydrolysis by 100% when used at a concentration of 20 μM and TNF-α-induced cell death in MCF-7 cells.1,2 It also reduces the inhibitory effects of oxidized 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphatidylcholine (OxPAPC) and the 5-keto-6-octendioic acid ester of 2-lysophosphatidylethanolamine (KOdiA-PE) on LPS-induction of IL-8 in human aortic endothelial cells.3 In vivo, GW 4869 (1 mg/kg) reverses hypoxia-induced pulmonary vasoconstriction in rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 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(9), 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(2), 296-302 (2009).

    Product Citations

    Leier, H.C., Weinstein, J.B., Kyle, J.E., et al. A global lipid map defines a network essential for Zika virus replication. Nat. Commun. 11(1), 3652 (2020).

    Hui, W.W., Hercik, K., Belsare, S., et al. Salmonella enterica serovar typhimurium alters the extracellular proteome of macrophages and leads to the production of proinflammatory exosomes. Infect. Immun. 86(2), e00386-00317 (2018).