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71012-19-6 , GA1-Ganglioside , Ganglio-N-tetraosylceramide; Ceramide tetrahexoside; GgOse4Cer; asialo-GM1

71012-19-6 , GA1-Ganglioside ,
Ganglio-N-tetraosylceramide;
Ceramide tetrahexoside;
GgOse4Cer;
asialo-GM1;
Cas:71012-19-6
C62H117N3O23 / 1272.6

GA1-Ganglioside , Ganglio-N-tetraosylceramide; Ceramide tetrahexoside; GgOse4Cer; asialo-GM1

Asialo GM1 is a sialic acid-depleted form of GM1 ganglioside, a molecule that is widely distributed throughout the central and peripheral nervous system, as well as other tissues in the body. The removal of sialic acid from GM1 leads to a significant reduction in the size of its head group, which changes its biological activity, modulating its cellular interactions and functional properties. This new form of GM1, asialo GM1, has been studied extensively due to its potential applications in scientific research and biotechnology, especially in the development of novel therapeutic strategies.

Definition and Background:

GM1 gangliosides are a group of glycolipids that are found on the cell surface of most vertebrate cells. They are composed of a ceramide lipid tail that anchors the molecule in the cell membrane, and a sialylated oligosaccharide head group that extends into the extracellular space. The sialic acid residues that decorate the head group are essential for the biological activity of GM1, since they interact with several classes of receptors on the surface of target cells, including growth factor receptors, adhesion molecules, and lectins.

Physical and Chemical Properties:

The physical and chemical properties of asialo GM1 are distinct from those of intact GM1, due to the lack of sialic acid residues in its oligosaccharide head group. Asialo GM1 is a smaller, less hydrophilic molecule, and has a different charge distribution compared to GM1. These differences can affect the solubility, stability, and functional properties of asialo GM1, making it a highly interesting molecule for researchers to investigate.

Synthesis and Characterization:

Asialo GM1 can be synthesized in the laboratory via chemical or enzymatic methods. The chemical synthesis involves the removal of sialic acid from GM1 using a strong acid or base, followed by purification of the asialo product using chromatography or electrophoresis. Enzymatic synthesis of asialo GM1 is achieved using sialidase enzymes, which catalyze the removal of sialic acid residues from GM1 or other sialylated glycolipids. The synthesized asialo GM1 can be characterized using several analytical techniques, including Thin Layer Chromatography, High-Performance Liquid Chromatography and Mass Spectrometry.

Analytical Methods:

The analytical methods used for the identification and quantification of asialo GM1 include spectrophotometric (UV-Visible spectroscopy), spectrofluorometric, enzyme-linked immunosorbent assay (ELISA) and gas chromatography-mass spectrometry (GC-MS). Researchers also use high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE) for the recognition of gangliosides from cell extracts.

Biological Properties:

Recent studies have shown that asialo GM1 can modulate several biological processes, including cell proliferation, differentiation, adhesion, and migration. Asialo GM1 has also been shown to have neuroprotective properties, inhibiting microglial activation and reducing oxidative stress. Furthermore, asialo GM1 can interact with Toll-like receptor 4 (TLR4) on the surface of immune cells, leading to the induction of IL-6 and other proinflammatory cytokines.

Toxicity and Safety in Scientific Experiments:

The safety and toxicity of asialo GM1 have been extensively studied in several animal models. The use of high doses of asialo GM1 showed an induction of neuronal toxicity, while lower doses showed no toxic effects. This suggests that asialo GM1 has a narrow therapeutic window and that dosing needs to be precise.

Applications in Scientific Experiments:

Asialo GM1 has several applications in scientific experiments, including the study of neurodegenerative diseases such as Alzheimer's and Parkinson's. Asialo GM1 has been shown to have a neuroprotective effect against oxidative stress and inflammatory factors that are associated with these diseases. Asialo GM1 has also been shown to have an ability in repairing injured nerves, leading to a potential use in regenerative medicine.

Current State of Research:

Currently, there is ongoing research on the mechanisms of asialo GM1 therapeutic approaches for several neurodegenerative diseases, and cancer. Further research has been directed towards drug delivery agents of asialo GM1 for cellular targeting. Asialo GM1 has been studied as a potential biomarker for specific biological activities, and research has been directed towards its potential as a drug target, therapy, or vaccine adjuvant.

Potential Implications in Various Fields of Research and Industry:

Asialo GM1 has an important role in various fields of research such as neuroscience, molecular biology, and biotechnology. The regenerative capacity shown by asialo GM1 raises hope that it would be utilized in regenerative therapies for damaged nerves. Asialo GM1 is also of value in designing novel therapeutic approaches for treating neurodegenerative disorders, cancers, and autoimmunoregulatory diseases. Asialo GM1 is also used in cryopreservation protocols for the preservation of biomolecules and cells.

Limitations and Future Directions:

The main limitation of asialo GM1 research is the associated toxicity at higher concentrations. The narrow therapeutic window for formulation of asialo GM1 limits treatment applications. Upcoming studies are directed towards investigating the optimal doses and protective mechanisms for patients. Advances in chemical and enzymatic synthesis of asialo GM1 have allowed access to large quantities and studying its effects in vitro provides promise for potential inclusion in regenerative medicine protocols. The future of asialo GM1 research could also be directed towards its investigation as a novel therapeutic approach for the treatment of autoimmune and neoplastic diseases.

Conclusion:

Asialo GM1 is an important variant of GM1 that has the potential to be used for therapeutic purposes. The physical and chemical properties of asialo GM1 alter the biological interactions allowing researchers to study it for its beneficial effects and potential therapeutic applications. Further progress in synthetic methods and analytical techniques will improve the study of asialo GM1 and broaden its potential clinical use. As such, asialo GM1 is a promising candidate for drug development and therapies, research and as a potential biomarker.

CAS Number71012-19-6
Product NameAsialo GM1
IUPAC NameN-[(E)-1-[(3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]octadecanamide
Molecular FormulaC62H117N3O23
Molecular Weight1272.6 g/mol
InChIInChI=1S/C62H114N2O23/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(71)64-40(41(70)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-80-60-54(78)51(75)57(44(36-67)83-60)86-62-55(79)52(76)56(45(37-68)84-62)85-59-47(63-39(3)69)58(49(73)43(35-66)81-59)87-61-53(77)50(74)48(72)42(34-65)82-61/h30,32,40-45,47-62,65-68,70,72-79H,4-29,31,33-38H2,1-3H3,(H,63,69)(H,64,71)/b32-30+/t40?,41?,42-,43-,44-,45-,47-,48+,49+,50+,51-,52-,53-,54-,55-,56+,57-,58-,59+,60?,61+,62+/m1/s1
InChI KeyVELGMVLNORPMAO-HMWOVMCASA-N
SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
Synonymsasialo GM1, asialo GM1 ganglioside, asialo GM1 glycolipid, ganglio-N-tetraosylceramide, ganglioside, asialo GM1
Canonical SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
Isomeric SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)NC(=O)C)O)O)O)O)C(/C=C/CCCCCCCCCCCCC)O


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