Kdo2-Lipid A (ready-to-use)
| Code | Size | Price |
|---|
| AG-CU1-0001-M001 | 1 mg | £125.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
+4°C
Storage:
4°C
Documents
Further Information
Alternate Names/Synonyms:
(3-Deoxy-D-manno-octulosonic acid)2-Lipid A
Appearance:
Clear, colorless solution.
CAS:
123621-04-5 (free base)
Concentration:
0.5mg/ml. Vial contains 2 ml.
EClass:
32160000
Form (Short):
liquid
Formulation:
Liquid. Sterile, ready-to-use solution in pyrogen-free double distilled water.
GHS Symbol:
GHS07
Handling Advice:
Keep sterile. Do not ingest. Wear gloves and mask. Avoid contact through all modes of exposure. Avoid inhalation and prevent from entering the bloodstream. Use must be restricted to qualified personnel.
Hazards:
H302, H312, H332, H413
InChi:
InChI=1S/C110H202N2O39P2.4H3N/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2;;;;/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138);4*1H3/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,109-,110-;;;;/m1../s1
InChiKey:
HBSUHPVFGADBOQ-USMMBHRMSA-N
Long 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.
MDL:
N/A
Molecular Formula:
C110H198N2Na4O39P2
Molecular Weight:
2326.7
Other data:
Strong activator (<10ng/ml) of toll-like receptor 4 (TLR4). Does not activate TLR2 or other TLRs as determined with splenocytes and macrophages from TLR4 deficient mice. No further re-extraction required. Isolated and purified from E. coli K12 heptose-deficient strain WBB06 (Re mutant) [1] by a modification of the PCP extraction method [2,3], converted to the uniform sodium salt form [4] and dissolved in sterile pyrogen-free double distilled water. Lit: [1] Deletion of the heptosyltransferase genes rfaC and rfaF in Escherichia coli K-12 results in a Re-type lipopolysaccharide with a high degree of 2-aminoethanol phosphate substitution: W. Brabetz, et al.; Eur. J. Biochem. 247, 716 (1997) / [2] A new method for the extraction of R lipopolysaccharides: C. Galanos, et al.; Eur. J. Biochem. 9, 245 (1969) / [3] Isolation and purification of R-form lipopolysaccharides: C. Galanos & O. Luderitz; Meth. Carbohydrate Chem. 9, 11 (1993) / [4] Electrodialysis of lipopolysaccharides and their conversion to uniform salt forms: C. Galanos & O. L?deritz; Eur. J. Biochem. 54, 603 (1975)
Package Type:
Vial
Precautions:
P270, P273, P280, P301, P312, P302, P352
Product Description:
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].
Purity:
Absence of detectable protein or DNA contaminants with agonistic TLR activity.
Signal Word:
Warning
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
Source / Host:
Isolated and purified from E. coli K12 heptose-deficient strain WBB06 (Re mutant).
Transportation:
Non-hazardous
UNSPSC Category:
Lipopolysaccharides
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at +4°C.
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)