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G0776

Sigma-Aldrich

Disialoganglioside-GD₂

from bovine brain, ~95%, Glycosphigolipid, lyophilized powder

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About This Item

CAS Number:
65988-71-8
MDL number:
MFCD00131133
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Disialoganglioside-GD2 from bovine brain, ~95%, lyophilized powder, semisynthetic

Quality Level

200

Assay

~95%

form

lyophilized powder

storage temp.

−20°C

SMILES string

N([C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)CO)O[C@H]2[C@H](O[C@H]([C@@H]([C@H]2O[C@]4(O[C@@H]([C@H]([C@@H](C4)O)N)C(O)C(O)CO[C@]5(O[C@@H]([C@H]([C@@H](C5)O)N)C(O)C(O)CO)C(=O)O)C(=O)O)O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)OCC(NC(=O)CCCCCCCCCCCCCCCCC)C(O)\C

InChI

1S/C74H134N4O32/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-52(89)78-43(44(84)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)40-101-69-61(95)60(94)63(50(38-81)104-69)106-70-62(96)67(64(51(39-82)105-70)107-68-55(77-42(3)83)59(93)58(92)49(37-80)103-68)110-74(72(99)100)35-46(86)54(76)66(109-74)57(91)48(88)41-102-73(71(97)98)34-45(85)53(75)65(108-73)56(90)47(87)36-79/h30,32,43-51,53-70,79-82,84-88,90-96H,4-29,31,33-41,75-76H2,1-3H3,(H,77,83)(H,78,89)(H,97,98)(H,99,100)/b32-30+/t43?,44?,45-,46-,47?,48?,49-,50-,51-,53+,54+,55-,56?,57?,58+,59-,60-,61-,62-,63-,64+,65+,66+,67-,68+,69-,70+,73-,74+/m1/s1

InChI key

FFILOTSTFMXQJC-QCFYAKGBSA-N

Amino Acid Sequence

Cer-Glc-Gal(NeuAc-NeuAc)-GalNAc

General description

Disialoganglioside GD2 is a cell surface-associated glycosphingolipid, which comprises sialic acid moiety and is regarded as a carbohydrate antigen.. It is expressed in the skin melanocytes, central and peripheral nervous system.
Gangliosides are major constituents of neuronal cell membranes and endoplasmic reticulum; contain a sialated polysaccharide chain linked to ceramide through a β-glycosidic linkage; for classification of gangliosides see Svennerholm, L., et al. (eds.), Structure and Function of Gangliosides, New York, Plenum, 1980.

Application

Disialoganglioside-GD2 from bovine brain has been used:
  • in the ganglioside- enzyme-linked immunosorbent assay (ELISA)
  • in capture ELISA with anti-GD2 antibody (ch14.18)
  • as a control to test its effect on reactivating autophagy in primary fibroblasts

Biochem/physiol Actions

Disialoganglioside GD2 is expressed in neuroblastoma, melanoma and small cell lung cancer. It is an immunotherapeutic target and is also regarded as a tumor-associated antigen. GD2 may favor cell migrationin tumors by promoting cell growth, as well as extracellular matrix component attachment.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000425897
0000425897
0000242359
0000242359
0000113336

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Nidale Tarek et al.
The Journal of clinical investigation, 122(9), 3260-3270 (2012-08-07)
Survival outcomes for patients with high-risk neuroblastoma (NB) have significantly improved with anti-disialoganglioside GD2 mAb therapy, which promotes NK cell activation through antibody-dependent cell-mediated cytotoxicity. NK cell activation requires an interaction between inhibitory killer cell immunoglobulin-like receptors (KIRs) and HLA
Fariba Navid et al.
Current cancer drug targets, 10(2), 200-209 (2010-03-06)
In the development of novel immune therapies for high-risk cancers, one goal is to find tumor targets that are not widely shared by normal cells. One such target is the surface disialoganglioside GD2. This antigen is expressed on the surface
Anastasia Shibina et al.
Journal of molecular medicine (Berlin, Germany), 91(4), 459-472 (2012-10-12)
Neuroblastoma (NB) is the most common extracranial solid tumor in children. Combining passive immunotherapy with an antibody to the disialoganglioside GD2 (ch14.18/SP2/0) and cytokines with 13-cis-retinoic acid for post-myeloablative maintenance therapy increased survival in high-risk NB, but the overall prognosis
Denis Cochonneau et al.
Cancer letters, 333(2), 194-204 (2013-02-02)
O-Acetyl-GD2 ganglioside is suitable antigen for tumor immunotherapy with specific therapeutic antibody. Here, we investigate the anti-tumor activity of O-acetyl-GD2-specific monoclonal antibody 8B6 on O-acetyl-GD2-positive tumor cells. The results indicated that mAb 8B6 induced growth inhibition of O-acetyl-GD2-expressing tumor cell
Min Shen et al.
International journal of nanomedicine, 7, 3319-3332 (2012-07-18)
Polyethylene glycol-grafted polyethylenimine (PEG-g-PEI) which was functionalized with a neuroblastoma cell-specific ligand, the GD2 single chain antibody (scAb(GD2)), was synthesized in order to effectively deliver Bcl-2 siRNA into neuroblastoma cells. This polymer was complexed first with superparamagnetic iron oxide nanoparticle
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