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N-glycolyl-Ganglioside GM3 Mixture (ammonium salt)

Catalog No. T36413 CAS 69345-49-9

Synonyms: N-glycolyl-Ganglioside GM3 Mixture (ammonium salt)

N-glycolyl-Ganglioside GM3(NeuGc-GM3) is a form of ganglioside GM3 that contains an N-glycolylated sialic acid (NeuGc).

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N-glycolyl-Ganglioside GM3 Mixture (ammonium salt) Chemical Structure

N-glycolyl-Ganglioside GM3 Mixture (ammonium salt), CAS 69345-49-9

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Biological Description

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Description

N-glycolyl-Ganglioside GM3(NeuGc-GM3) is a form of ganglioside GM3 that contains an N-glycolylated sialic acid (NeuGc).

In vitro

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 cellsviathe diet and incorporated into glycolipids, such as ganglioside GM3.1,2NeuGc-GM3 impairs differentiation and maturation of dendritic cellsin vitroand reduces CD4 expression in non-activated T cells.1,3It increases the number of lung tumor nodules formed in a murine Lewis lung carcinoma model.4It is found in a variety of human cancers, including breast and lung cancers, as well as pediatric cancers.1Levels of NeuGc-GM3 are negatively correlated with the number of mature dendritic cells in patient-derived non-small cell lung cancer (NSCLC) tumor tissue.5Anti-NeuGc-GM3 antibodies, able to destroy tumor cells in vitro, have been found in individuals without cancer but not in patients with NSCLC.1,6N-glycolyl-Ganglioside GM3mixture contains ganglioside GM3molecular species with primarily C22:0, C23:0, and C24:0 fatty acyl chain lengths.

Synonyms	N-glycolyl-Ganglioside GM3 Mixture (ammonium salt)
Molecular Weight	1284.7
Formula	C64H117N2O22NH4
CAS No.	69345-49-9

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

References and Literature

1. Labrada, M., Dorvignit, D., Hevia, G., et al.GM3(Neu5Gc) ganglioside: An evolution fixed neoantigen for cancer immunotherapySemin. 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 acidProc. Natl. Acad. Sci. USA100(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 functionInt. 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 cancerFront. Oncol.2160(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 cancerBMC Cancer9180(2009) 6. Rodríguez-Zhurbenko, N., Martínez, D., Blanco, R., et al.Human antibodies reactive to NeuGcGM3 ganglioside have cytotoxic antitumor propertiesEur. J. Immunol.43(3)826-837(2013)

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Keywords

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