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ProductsBack/Kdo2-Lipid A (ready-to-use) [123621-04-5]
Chemical Structure
Chemical Structure
Chemical Structure

Kdo2-Lipid A (ready-to-use) [123621-04-5]

Research Use Only
AG-CU1-0001
AdipoGen Life Sciences
CAS Number123621-04-5
DownloadMSDS
Product group Chemicals
Molecular Weight2326.7
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Kdo2-Lipid A (ready-to-use) [123621-04-5]
  • Delivery Days Customer
    10
  • CAS Number
    123621-04-5
  • Certification
    Research Use Only
  • Concentration
    0.5 mg/ml
  • Formulation
    Liquid
  • Hazard Information
    Warning
  • Molecular Formula
    C110H198N2Na4O39P2
  • Molecular Weight
    2326.7
  • Scientific Description
    Chemical. CAS: 123621-04-5 (free base). Formula: C110H198N2Na4O39P2. MW: 2326.7. Isolated and purified from E. coli K12 heptose-deficient strain WBB06 (Re mutant). Defined substructure of the Re mutant of lipopolysaccharide (LPS). Endotoxin activity equal to Re LPS. Strong activator (<10ng/ml) of macrophages via toll-like receptor 4 (TLR4). Does not activate TLR2 or other TLRs as determined with splenocytes and macrophages from TLR4 deficient mice by IL-6 ELISA. Facilitates the structural analysis of its complexes with signaling receptors, such as TLR4/MD2 and CD14. Kdo2-Lipid A was used in a recent animal atherosclerosis model. Induces sphingolipid biosynthesis, which is essential for induction of autophagy. - Defined substructure of the Re mutant of lipopolysaccharide (LPS) [1]. Endotoxin activity equal to Re LPS [1]. Strong activator (<10ng/ml) of macrophages via toll-like receptor 4 (TLR4) [1, 2, 3, 4, 9]. Does not activate TLR2 [5] or other TLRs as determined with splenocytes and macrophages from TLR4 deficient mice by IL-6 ELISA [1,4]. Facilitates the structural analysis of its complexes with signaling receptors, such as TLR4/MD2 [1,2] and CD14 [7]. Kdo2-Lipid A was used in a recent animal atherosclerosis model [6]. Induces sphingolipid biosynthesis, which is essential for induction of autophagy [8].
  • SMILES
    [Na+].[Na+].[Na+].[Na+].CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)OC1[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OCC2O[C@H](OP(O)([O-])=O)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)C(OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)OC(CO[C@@]2(CC(O[C@@]3(CC(O)[C@@H](O)C(O3)[C@@H](O)CO)C([O-])=O)[C@@H](O)C(O2)[C@@H](O)CO)C([O-])=O)[C@H]1OP(O)([O-])=O
  • Storage Instruction
    2°C to 8°C
  • UNSPSC
    12352200

References

  • Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4: C.R. Raetz, et al.; J. Lipid Res. 47, 1097 (2006)
  • Aggregation behavior of an ultra-pure lipopolysaccharide that stimulates TLR-4 receptors: H. Sasaki & S.H. White; Biophys. J. 95, 986 (2008)
  • TLR-4 mediated group IVA phospholipase A(2) activation is phosphatidic acid phosphohydrolase 1 and protein kinase C dependent: A. Grkovich, et al.; BBA 1791, 975 (2009)
  • Subcellular organelle lipidomics in TLR 4-activated macrophages: A.Y. Andreyev, et al.; J. Lipid Res. 51, 2785(2010)
  • Spinal glial TLR4-mediated nociception and production of prostaglandin E and TNF: O. Saito, et al.; Br. J. Pharmacol. 160, 1754 (2010)
  • Low doses of lipopolysaccharide and minimally oxidized low-density lipoprotein cooperatively activate macrophages via nuclear factor kappab and activator protein-1- possible mechanism for acceleration of atherosclerosis by subclinical endotoxemia: P. Wiesner, et al.; Circ. Res. 107, 56 (2010)
  • NMR spectral mapping of Lipid A molecular patterns affected by interaction with the innate immune receptor CD14: S. Albright, et al.; BBRC 378, 721 (2009)
  • Kdo2-lipid A, a TLR4-specific agonist, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy: K. Sims, et al.; J. Biol. Chem. 285, 28568 (2010)
  • ATF3 plays a key role in Kdo2-lipid A-induced TLR4-dependent gene expression via NF-?B activation: E.Y. Kim, et al.; PLoS One 5, e14181 (2010)