ASIALOGANGLIOSIDE-GM2 Chemical Properties

storage temp. 

−20°C

solubility 

Chloroform:Methanol:Water (2:1:0.1): Soluble

form 

lyophilized powder

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

ASIALOGANGLIOSIDE-GM2 Usage And Synthesis

Description

Ganglioside G_M2 asialo (asialo- G_M2) is a glycosphingolipid containing three monosaccharide residues and a fatty acid of variable chain length but lacking the sialic acid residue present on ganglioside M₂. Asialo-G_M2 levels are low-to-undetectable in normal human brain, but it accumulates in the brain of patients with Tay-Sachs and Sandhoff disease, which are neurodegenerative disorders characterized by deficiency of lysosomal β-hexosaminidase A and B, respectively. It also binds to various bacteria, including Pseudomonas isolates derived from cystic fibrosis patients. Asialo-G_M2 mixture contains ganglioside G_M2 asialo molecular species with fatty acyl chains of variable lengths. [Matreya, LLC. Catalog No. 1512]

Chemical Properties

Gls have two basic functions: mediating cell-cell, cell-microbe, and cell-matrix interactions. It regulates the function of proteins in the cytoplasmic membrane, such as growth factor receptors and isolated channels. Exogenous Gls can alter the activity of activating enzymes linked to Gls by binding to Gls-binding proteins on the cell surface, thereby increasing or decreasing the rate of cell growth. The pathogenesis of hypoxic-ischemic brain injury is related to a variety of factors. Animal experiments at home and abroad have confirmed that gangliosides can pass the blood-brain barrier, prevent apoptosis of nerve cells, stabilize the nerve cell membrane, maintain calcium balance, anti-excitatory amino acid neurotoxicity and oxygen radical reaction, and synergize with nerve growth factor to play a neurotrophic role. Clinically, ganglioside lipids have been used in the treatment of cerebral ischemia. Chen, Xiaolong and Pan, Xiaoli et al. Searching for biological markers of retinoblastoma (RB). METHODS: High-performance thin-layer chromatography (HPLC) was applied for the controlled analysis of gangliosides from 32 cases of RB tumor tissues and 21 cases of control retinal tissues. RESULTS: The ganglioside-bound sialic acid content of RB tumor tissues was significantly lower than that of control retinal tissues [(0.04±0.01) mg/g (wet wt.), (0.11±0.02) mg/g (wet wt.), P<0.01].GM3, GM2, GM1, GD3, and GD2 were the major components of the RB tumor tissues, whereas GM2 was the main component in the control retinal tissues, GM1, GD1a, GT1b and GQ1b were predominant in control retinal tissues. Fu Qiang and Hou Tiesheng concluded that gangliosides have a significant protective effect on injured spinal cord tissues and initially explored their mechanism of action, which may be through the blockade of neuronal apoptosis. Parkinson's disease (PD) is a progressive degenerative disease of the substantia nigra striata. In recent years, it has been found that gangliosides are expected to alleviate the symptoms and delay the progression of the disease.GM1 has some early preventive effects on hypoxic brain damage in aged rats, and the mechanism of action may be closely related to the antagonism of excitatory amino acid toxicity effects, prevention of intracellular calcium-ion balance disorders, attenuation of free radicals damage, and the protection of membrane enzyme activity.GM3, containing two hexose groups and one sialic acid group, induces GM3 contains two hexosyl groups and one sialic acid group, which can induce the differentiation of HL-60 cells along the monocyte macrophage pathway and regulate the phospholipid metabolism of J6-2 cells. Li Zhaojie and Zhou Dong et al. explored the application of monosialic acid tetrahexose ganglioside (GM1) in the treatment of acute craniocerebral injury. The results showed that GM1 has a better effect of catalyzing awakening, and has a better efficacy in improving the quality of survival of patients, reducing the mortality rate, and promoting the recovery of brain function. Zhang Guilin and Fu Wanhai observed the therapeutic effect of ganglioside (GM1) on hypoxic-ischemic (HI) neonatal rats and its effect on the expression of apoptosis-related gene Bax/Bcl-2. The results showed that the application of GM1 to treat HI brain injury could reduce brain cell apoptosis, GM1 treatment had a certain effect on the expression of apoptosis-related genes Bax/Bcl-2, and apoptosis after HI brain injury might be related to these two genes. Ganglioside GD3 has the effect of enhancing angiogenesis in the tumor itself and adjacent tissues, thus promoting tumor evolution and metastasis. The research work of Gao Luoyi and Zeng Guichao provided strong experimental evidence for this hypothesis. The application of the anti-intentional DNA of GD3 synthase to transfect the tumor cells thereby inhibiting the expression of GD3 synthase in the cells greatly reduced the endogenous GD3 content of the cells, and further studies proved that the inhibition of the synthesis of GD3 in the tumor cells significantly reduced the vascular endothelial growth factor (WVGF) level and minimized the angiogenic effect, these experiments indicate that GD3 has an important role in tumor angiogenesis, in addition, GD3 as a tumor-associated antigen, its synergistic effect with angiogenic factors plays an important role in combination gene therapy. Domestic and international studies on tumor-associated sphingolipids have mainly focused on acidic sphingolipids, i.e., gangliosides, while neutral sphingolipids have been less studied. According to Svennerholm L. and Zhang Shizhong et al, there are two methods for color development of neutral sphingolipids, which are similar in principle, mainly due to the irreversible binding of acid to the sugar groups in the sphingolipids, which in turn makes the neutral sphingolipids blue or purple-red depending on the color developer. Zhang Zongcheng et al. established a new color development method for neutral sphingolipids, iodine color development method, which is based on the principle that unsaturated bonds can attract iodine atoms to gather and generate brownish-yellow substances around them. Since gangliosides also contain double bonds, whether this color development method is applicable to the color development of gangliosides needs to be further studied.

Uses

Ganglioside GM2, Asialo is a semisynthetic ganglioside.

General Description

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.

Biochem/physiol Actions

Degraded form of Asialoganglioside-GM1 ganglioside.

References

[1] HOWARD C. KRIVAN  David D R  Victor Ginsburg. Pseudomonas aeruginosa and Pseudomonas cepacia isolated from cystic fibrosis patients bind specifically to gangliotetraosylceramide (asialo GM1) and gangliotriaosylceramide (asialo GM2)[J]. Archives of biochemistry and biophysics, 1988, 260 1: Pages 493-496. DOI: 10.1016/0003-9861(88)90473-0

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