N-Hexadecanoyl-D9 (13,13,14,14,15,15,16,16,16)-monosialoganglioside GM3 (NH4+ salt)/N-十六烷酰基-D9 (13,13,14,14,15,15,16,16,16)-单唾液酸神经节苷脂GM3 (NH4+ salt)

Specifications

• Catalog #:2059

• Scientific Name:N-Hexadecanoyl-D₉ (13,13,14,14,15,15,16,16,16)-monosialoganglioside GM₃(NH₄⁺ salt)

• Common Name:GM₃-D₉; N-CD₉-Palmitoyl-GM₃

• Empirical Formula:C₅₇H₉₅D₉N₂O₂₃•NH₃

• SDS:View Safety Data Sheet

• Data Sheet:View Data Sheet

• Formula Weight:1163 + NH₃

• Unit:500 µg

• Source:semisynthetic, bovine buttermilk

• Purity:98+%

• Analytical Methods:TLC; identity confirmed by MS

• Solubility:Chloroform/methanol/DI water, 2:1:0.1; forms micellar solution in water

• Physical Appearance:solid

• Storage:-20℃

• Dry Ice:No

• Hazardous:No

Description

Application Notes:

这种氘化的神经节苷脂是使用质谱鉴定样品和生物系统中的神经节苷脂理想的标准品。神经节苷脂是酸性的鞘糖脂，在细胞膜的外层形成脂筏，特别是在中枢神经系统的神经元细胞中，参与细胞增殖、分化、粘附、信号转导、细胞间相互作用、肿瘤发生和转移。神经节苷脂的积累与多种疾病有关，包括泰-萨克斯病和山德霍夫病。GM3是人成纤维细胞的主要神经节苷脂，能调节成纤维细胞和表皮生长因子s，还能调节多种癌细胞系的粘附和迁移。GM3也能抑制肿瘤细胞的侵袭。GM3可诱导人早幼粒细胞白血病HL-60细胞向单核/巨噬细胞分化，而不是向粒细胞分化.

This deuterated ganglioside is ideal for the identification of gangliosides in samples and biological systems using mass spectrometry.¹ Gangliosides² are acidic glycosphingolipids that form lipid rafts in the outer leaflet of the cell plasma membrane, especially in neuronal cells in the central nervous system.³ They participate in cellular proliferation, differentiation, adhesion, signal transduction, cell-to-cell interactions, tumorigenesis, and metastasis.⁴ The accumulation of gangliosides has been linked to several diseases including Tay-Sachs and Sandhoff disease. GM₃ is the main ganglioside of human fibroblasts and can regulate fibroblast and epidermal growth factors⁵ and is also able to regulate the adhesion and migration of several carcinoma cell lines. GM₃ was also shown to inhibit tumor cell invasion. GM₃ can induce human promyelocytic leukemia HL-60 cells to differentiate to monocyte/macrophage lineage instead of granulocytes.⁶

References:
1. J. Gu, C. Tifft and S. Soldin “Simultaneous quantification of GM1 and GM2 gangliosides by isotope dilution tandem mass spectrometry” Clinical Biochemistry, Vol. 41(6) pp. 413-417, 2008
2. L. Svennerholm, et al. (eds.), Structure and Function of Gangliosides, New York, Plenum, 1980
3. T. Kolter, R. Proia, K. Sandhoff “Combinatorial Ganglioside Biosynthesis” J. Biol. Chem., Vol. 277:29, pp. 25859-25862, 2002
4. S. Birkle, G. Zeng, L. Gao, R. K. Yu, and J. Aubry “Role of tumor-associated gangliosides in cancer progression” Biochimie, Vol. 85 pp. 455–463, 2003
5. E. G. Bremer, J. Schlessinger, and S. Hakomori “Ganglioside-mediated modulation of cell growth. Specific effects of GM3 on tyrosine phosphorylation of the epidermal growth factor receptor” J. Biol. Chem., Vol. 261 pp. 2434–2440, 1986 6. T. Chung, H. Choi, Y. Lee, and C. Kim “Molecular mechanism for transcriptional activation of ganglioside GM3 synthase and its function in differentiation of HL-60 cells” Glycobiology, Vol. 15:3, pp. 233-244, 2004