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N-Hexanoyl-biotin-disialoganglioside GD3/N-乙酰基-生物素-双唾液酸神经节苷脂GD3


  • Catalog #:2055

  • Scientific Name:N-Hexanoyl-biotin-disialoganglioside GD3

  • Common Name:Biotin-C6:0-GD3

  • Empirical Formula:C68H116N6O31S • 2NH3

  • SDS:View Safety Data Sheet

  • Data Sheet:View Data Sheet

  • Formula Weight:1546 + 2NH3

  • Unit:500 µg

  • Source:semisynthetic, bovine buttermilk

  • Purity:98+%

  • Analytical Methods:TLC; identity confirmed by MS

  • Solubility:chloroform/methanol/water 2:1:0.1

  • Physical Appearance:solid

  • Storage:-20℃

  • Dry Ice:No

  • Hazardous:No


Application Notes:

这种神经节苷脂GD3类似物含有一个生物素单元,通过己酸连接子连接到鞘苷部分的胺上,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。二硫根神经节苷脂GD3主要在神经元发育过程中表达,其在成人组织中的表达非常有限。GD3在基底细胞癌和恶性黑色素瘤中的表达异常高,被认为是一种人类黑色素瘤特异性抗原。尽管GD3不是免疫原性的,它已经被研究作为免疫靶向人类黑色素瘤细胞的工具GD3的过度表达通过向凋亡通路招募线粒体、抑制NF-κB激活和随后的κ b依赖基因诱导而导致细胞凋亡GD3水平的升高也被发现与增生性疾病(如动脉粥样硬化)有关。

This ganglioside GD3 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. Disialoganglioside GD3 is predominantly expressed during neuronal development and its expression becomes very limited in adult tissues. GD3 expression is unusually high in basal cell carcinomas and malignant melanomas and is thought to be a human melanoma-specific antigen. Although GD3 is not immunogenic it has been investigated as a tool for immunotargeting human melanoma cells.4 Over expression of GD3 has led to apoptosis by recruiting mitochondria to apoptotic pathways and suppressing NF-κB activation and subsequent κB-dependent gene induction.5 Increased levels of GD3 have also been found to be associated with proliferative diseases, such as atherosclerosis.

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. H. Jennings et al. “Bioengineering of Surface GD3 Ganglioside for Immunotargeting Human Melanoma Cells” Journal of Biological Chemistry, Vol. 279:24 pp. 25390, 2004
5. J. Fernández-Checa et al. “Ganglioside GD3 Sensitizes Human Hepatoma Cells to Cancer Therapy” Journal of Biological Chemistry, Vol. 277:51 pp. 49870, 2002