A ganglioside
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N-glycolyl-Ganglioside GM3 (ammonium salt)

Item No. 33263

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-O-[O-[N-(hydroxyacetyl)-α-neuraminosyl]-(2→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]-ceramide
CAS Number
69345-49-9
Synonyms
  • GM3-Neugc
  • NeuGc-GM3
  • NGcGM3
  • N-glycolyl-GM3
  • N-glycolyl-Monosialoganglioside GM3
  • N-Glycolylneuraminyllactosylceramide
Molecular Formula
C64H117N2O22 • NH4 (for tricosanoyl)
Formula Weight
1284.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:DI Water (2:1:0.1): soluble
SMILES
O[C@H]1[C@H](O[C@@H]([C@@H]([C@H]2O[C@]3(C([O-])=O)C[C@@H]([C@H]([C@]([C@@H]([C@H](O)CO)O)(O3)[H])NC(CO)=O)O)O)O[C@@H]([C@@H]2O)CO)[C@@H](CO)O[C@@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC([R])=O)[C@@H]1O.[NH4+]
InChi Code
InChI=1S/C64H118N2O22.H3N/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-50(74)65-44(45(71)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2)43-83-61-56(79)55(78)58(49(41-69)85-61)86-62-57(80)60(54(77)48(40-68)84-62)88-64(63(81)82)38-46(72)52(66-51(75)42-70)59(87-64)53(76)47(73)39-67;/h34,36,44-49,52-62,67-73,76-80H,3-33,35,37-43H2,1-2H3,(H,65,74)(H,66,75)(H,81,82);1H3/b36-34+;/t44-,45+,46-,47+,48+,49+,52+,53+,54-,55+,56+,57+,58+,59+,60-,61+,62-,64-;/m0./s1
InChi Key
ODSNHGRWQUWHAN-GHFHROAOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $869

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    Product Description

    N-glycolyl-Ganglioside GM3 (NeuGc-GM3) is a form of ganglioside GM3 that contains an N-glycolylated sialic acid (NeuGc). It is not biosynthesized in humans under baseline conditions due to a mutation in CMP-Neu5Ac hydroxylase (CMAH), which converts N-acetyl sialic acid to N-glycolyl sialic acid, but NeuGc can be taken up by human cells via the diet and incorporated into glycolipids, such as ganglioside GM3.1,2 NeuGc-GM3 impairs differentiation and maturation of dendritic cells in vitro and reduces CD4 expression in non-activated T cells.1,3 It increases the number of lung tumor nodules formed in a murine Lewis lung carcinoma model.4 It is found in a variety of human cancers, including breast and lung cancers, as well as pediatric cancers.1 Levels of NeuGc-GM3 are negatively correlated with the number of mature dendritic cells in patient-derived non-small cell lung cancer (NSCLC) tumor tissue.5 Anti-NeuGc-GM3 antibodies, able to destroy tumor cells in vitro, have been found in individuals without cancer but not in patients with NSCLC.1,6 This product contains ganglioside GM3 molecular species with primarily C22:0, C23:0, and C24:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1553]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Labrada, M., Dorvignit, D., Hevia, G., et al. GM3(Neu5Gc) ganglioside: An evolution fixed neoantigen for cancer immunotherapy. Semin. Oncol. 45(1-2), 41-51 (2018).

    2. Tangvoranuntakul, P., Gagneux, P., Diaz, S., et al. Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid. Proc. Natl. Acad. Sci. USA 100(21), 12045-12050 (2003).

    3. de León, J., Fernández, A., Clavell, M., et al. Differential influence of the tumour-specific non-human sialic acid containing GM3 ganglioside on CD4+CD25- effector and naturally occurring CD4+CD25+ regulatory T cells function. Int. Immunol. 20(4), 591-600 (2008).

    4. Segatori, V.I., Vazquez, A.M., Gomez, D.E., et al. Preclinical evaluation of racotumomab, an anti-idiotype monoclonal antibody to N-glycolyl-containing gangliosides, with or without chemotherapy in a mouse model of non-small cell lung cancer. Front. Oncol. 2, 160 (2012).

    5. van Cruijsen, H., Ruiz, M.G., van der Valk, P., et al. Tissue micro array analysis of ganglioside N-glycolyl GM3 expression and signal transducer and activator of transcription (STAT)-3 activation in relation to dendritic cell infiltration and microvessel density in non-small cell lung cancer. BMC Cancer 9, 180 (2009).

    6. Rodríguez-Zhurbenko, N., Martínez, D., Blanco, R., et al. Human antibodies reactive to NeuGcGM3 ganglioside have cytotoxic antitumor properties. Eur. J. Immunol. 43(3), 826-837 (2013).