O-Acetyl-Gangliosides

9-O-Acetyl-GD3

Stability of 9-O-Acetyl Gangliosides:

9-O-Acetyl gangliosides readily revert to their non-acetylated form. They have a shelf life of approximately 3 months when stored at -20°C. Long term storage of these compounds will result in a mixture of the acetylated and non-acetylated gangliosides. Therefore Matreya produces and purifies 9-O-acetyl gangliosides on a custom basis, to ensure the highest purity of the acetylated product. Please contact us for a free quote.


Product Name

9-O-Acetyl-monosialoganglioside GM1 SPL4906
9-O-Acetyl-disialoganglioside GD3 SPL4907
Please contact Matreya for other O-Acetyl-Gangliosides


Gangliosides are sialic acid containing glycosphingolipids that play important roles in cell adhesion, cell recognition, signal transduction, and neural development. O-Acetylation of hydroxyl groups on the sialic acid is one of the most common modifications of gangliosides and can exist acetylated to the C-4, 7, 8 and 9 hydroxyl groups. This causes major changes in their physiological properties, resistance to sialidase hydrolysis, and lectin binding. Acetylated gangliosides have especially been correlated with various cancers.(1)

While an accumulation of the ganglioside GD3 is known to induce apoptosis, acetylation to 9-O-acetyl-GD3 renders it unable to trigger this important function. Because of this, there is a critical ratio between GD3 and 9-O-acetyl GD3 which promotes tumor survival in glioblastoma cell cultures. In glioblastoma cells, cleaving the acetyl group of 9-O-acetyl-GD3 restores normal GD3, resulting in a reduction in tumor cell viability while normal astrocytes remain unaffected.(2)

Expression of 9-O-acetyl GD3 increases in Schwann cells (SC) following infection with Mycobacterium leprae (ML), the etiologic agent of leprosy. Immunoblockage of 9-O-acetyl GD3 in vitro significantly reduces adhesion of ML to SC surfaces.(1)

The O-acetylated-derivative of GD2 has recently received attention as a novel antigen to target GD2-positive cancers. The absence of O-acetyl-GD2 expression on nerve fibers and the lack of allodynic properties of anti-GD2 antibodies, which are believed to play a major role in mediating anti-GD2 therapeutic antibodie’s dose-limiting side effects, provide an important rationale for the clinical application of immunotherapeutic strategies in patients with O-acetyl-GD2-expressing tumors.(3)

References:
1. V. Ribeiro-Resende et al. Involvement of 9-O-Acetyl GD3 Ganglioside in Mycobacterium leprae infection of Schwann Cells. The Journal of Biological Chemistry. 285, 34086-34096 (2010)
2. S. Birks et al. Targeting the GD3 acetylation pathway selectively induces apoptosis in glioblastoma. Neuro Oncol. 13(9), 950-60 (2011)
3. J. Fleurence et al. Targeting O-Acetyl-GD2 Ganglioside for Cancer Immunotherapy. Journal of Immunology Research. Article ID 5604891 (2017)