A ganglioside
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Ganglioside GM3 (bovine brain) (sodium salt)

Item No. 15587

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
54827-14-4
Synonyms
  • Hematoside
  • Sialosyllactosylceramide
Molecular Formula
C59H107N2O21 • Na (for tricosanoyl)
Formula Weight
1203.5
Purity
≥98%
Formulation (Request formulation change)
A lyophilized solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): SolubleWater: Forms micellar solution
SMILES
O[C@@H]1[C@@H]([C@H]([C@@H](O[C@@H]1CO)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2CO)OC[C@@]([H])([C@](O)(/C=C/CCCCCCCCCCCCC)[H])NC(CCCCCCCCCCCCCCCCC)=O)O)O)O)O[C@]3(O[C@H]([C@@H]([C@H](C3)O)NC(C)=O)[C@@]([H])([C@]([H])(O)CO)O)C([O-])=O.[Na+]
InChi Code
InChI=1S/C59H108N2O21.Na/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(69)61-40(41(66)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-77-56-51(73)50(72)53(45(37-64)79-56)80-57-52(74)55(49(71)44(36-63)78-57)82-59(58(75)76)34-42(67)47(60-39(3)65)54(81
InChi Key
GGQRTSSCXQEZNW-BLVJLEROSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $262

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    Product Description

    Ganglioside GM3 is a monosialoganglioside that demonstrates antiproliferative and pro-apoptotic effects in tumor cells by modulating cell adhesion, proliferation, and differentiation.1,2 It suppresses angiogenesis and reduces proliferation and migration of human umbilical vein endothelial cells (HUVECs) when used at a concentration of 20 μM via inhibition of VEGFR2 and Akt phosphorylation.1,2 Ganglioside GM3 induces dissociation of the insulin receptor-caveolin-1 complex from lipid microdomains, functioning as an inhibitor of insulin signaling and contributing to insulin resistance in adipocytes.3 This product contains ganglioside GM3 molecular species with primarily C18:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mukherjee, P., Faber, A.C., Shelton, L.M., et al. Thematic review series: Sphingolipids. Ganglioside GM3 suppresses the proangiogenic effects of vascular endothelial growth factor and ganglioside GD1a. J. Lipid Res. 49(5), 929-938 (2008).

    2. Seyfried, T.N., and Mukherjee, P. Ganglioside GM3 is antiangiogenic in malignant brain cancer. J. Oncol. 961243 (2010).

    3. Kabayama, K., Sato, T., Saito, K., et al. Dissociation of the insulin receptor and caveolin-1 complex by ganglioside GM3 in the state of insulin resistance. Proc. Natl. Acad. Sci. USA 104(34), 13678-13683 (2007).