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G0776

Disialoganglioside-GD₂

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

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About This Item

CAS Number:
65988-71-8
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00131133
Assay:
~95%
Form:
lyophilized powder
Quality level:
200

Key Documents

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Product Name

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

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

assay

~95%

form

lyophilized powder

storage temp.

−20°C

Quality Level

200

Related Categories

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000425897
0000425897
0000242359
0000242359
0000113336

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Wenyong Tong et al.
Methods in molecular biology (Clifton, N.J.), 928, 39-52 (2012-09-08)
Ganglioside GD2 is a cell surface glycosphingolipid that is targeted clinically for cancer diagnosis, prognosis, and therapy. The conformations of free GD2 and of GD2 bound to anti-GD2 mAb 3F8 were resolved by saturation transfer difference nuclear magnetic resonance and
Marie Vincent et al.
International journal of cancer, 133(3), 757-765 (2013-01-29)
Immunocytokines (ICKs) targeting cytokines to the tumor environment using antibodies directed against a tumor-associated antigen often have a higher therapeutic index than the corresponding unconjugated cytokines. Various ICKs displaying significant antitumoral effects in several murine tumor models have already been
S L Pichla et al.
Journal of structural biology, 119(1), 6-16 (1997-06-01)
The GD2 ganglioside is a cell-surface component that appears on the surface of metastatic melanoma cells and is a marker for the progression of the disease. The ME36.1 monoclonal antibody binds to the GD2 ganglioside and has shown potential as
Jan Müller et al.
PloS one, 11(10), e0163648-e0163648 (2016-10-08)
Neuroectodermal tumours are characterized by aberrant processing of disialogangliosides concomitant with high expression of GD2 or GD3 on cell surfaces. Antibodies targeting GD2 are already in clinical use for therapy of neuroblastoma, a solid tumour of early childhood. Here, we
Daisuke Sakai et al.
Nature communications, 3, 1264-1264 (2012-12-13)
Despite the high prevalence of intervertebral disc disease, little is known about changes in intervertebral disc cells and their regenerative potential with ageing and intervertebral disc degeneration. Here we identify populations of progenitor cells that are Tie2 positive (Tie2+) and
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