N-Hexanoyl-biotin-monosialoganglioside GM3 (NH4+ salt)/N-乙酰基-生物素-单唾液酸神经节苷脂GM3 (NH4+ salt)
Specifications
Catalog #:2056
Scientific Name:N-Hexanoyl-biotin-monosialoganglioside GM3 (NH4+ salt)
Common Name:Biotin-C6:0-GM3
Empirical Formula:C57H99N5O23S • NH3
SDS:View Safety Data Sheet
Data Sheet:View Data Sheet
Formula Weight:1254 + HN3
Unit:500 µg
Source:semisynthetic, bovine buttermilk
Purity:98+%
Analytical Methods:TLC; identity confirmed by MS
Solubility:chloroform/methanol/water, 2:1:0.1; water
Physical Appearance:solid
Storage:-20℃
Hazardous:No
Description
Application Notes:
这种神经节苷脂GM3类似物含有一个生物素单元，该生物素单元通过己酸连接子连接到鞘氨醇部分的胺上，非常适合用于神经节苷脂研究。生物素结构允许神经节苷脂附着到链霉亲和素和亲和素底物上，使其在与底物结合和毒素检测方面非常有用神经节苷脂是含有一种或多种唾液酸的酸性鞘糖脂，通常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。它们参与许多细胞活动，包括增殖、分化、黏附、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，而对神经节苷脂的自身免疫反应可导致格林-巴利综合征。神经节苷脂作为各种毒素和细菌的受体，在各种肿瘤中积累，并协助许多神经功能。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s4，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 ganglioside GM3 analogue contains a biotin unit attached to the amine of the sphingosine moiety via a hexanoic acid linker and is ideal for use in ganglioside studies. The biotin structure allows for attachment of the ganglioside to streptavidin and avidin substrates making it extremely useful for binding to substrates and for toxin detection.1 Gangliosides are acidic glycosphingolipids containing one or more sialic acids that generally form lipid rafts in the outer leaflet of the cell plasma membrane, especially in neuronal cells in the central nervous system.2,3 They participate in many cellular activities including 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 while an autoimmune response against gangliosides can lead to Guillain-Barre syndrome. Gangliosides act as receptors for various toxins and bacteria, accumulate in various tumors, and aid in many neuronal functions. GM3 is the main ganglioside of human fibroblasts and can regulate fibroblast and epidermal growth factors4 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.5
Selected References:
1. A. Pukin et al. Chemoenzymatic synthesis of biotin-appended analogues of gangliosides GM2, GM1, GD1a and GalNAc-GD1a for solid-phase applications and improved ELISA tests. Org. Biomol. Chem., 9(16):5809-5815, 2011
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., July Vol. 277, No. 29, pp. 25859-25862, 2002
4. 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
5. 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
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