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L5399

Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant)

Synonym(s):

Diphosphoryl Lipid A from E.Coli.

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About This Item

NACRES:
NA.25
PubChem Substance ID:
24896402
UNSPSC Code:
12352211
MDL number:
MFCD00131510

Key Documents

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InChI key

GZQKNULLWNGMCW-UHFFFAOYSA-N

SMILES string

CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP(O)(O)=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(CO)C1OP(O)(O)=O

InChI

1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)

biological source

Escherichia coli (F583 Rd mutant)

form

lyophilized powder

shipped in

ambient

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant) has been used:
  • to study the effect of various lipid A molecules on lung pericyte proliferation in vitro
  • to test on THP-1 and J774A.1 cells for neopterin and nitrite formation respectively
  • as lipopolysaccharides (LPS) derivatives in binding experiments
  • to stimulate the spleen cells and as a mitogen stimulation for toll like receptor 4 (TLR4)

Biochem/physiol Actions

Lipid A is mainly essential for the robust immunostimulatory activities of lipopolysaccharides (LPS) in human. Lipid A is the hydrophobic domain of LPS helps in anchoring LPS to the plasma membrane of bacteria. It is immunologically active and an important constituent of LPS recognised by immune system.

General description

Lipid A is the fundamental structure of lipopolysaccharides (LPS), present in bacteria.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000486028
0000486028
0000406510
0000406510
0000367391

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Effects of Endotoxin on Lung Pericytesin Vitro
Khoury J and Langleben D
Microvascular Research, 56(2), 71-84 (1998)
Graham Goldsworthy et al.
Journal of insect physiology, 49(8), 795-803 (2003-07-26)
Interactions between the locust endocrine and immune systems have been studied in vivo in relation to nodule formation and activation of the prophenoloxidase cascade in the haemolymph. Injection of bacterial lipopolysaccharide (LPS) extracted from Escherichia coli induces nodule formation in
Biological activities of lipid A complexed with bovine-serum albumin.
C Galanos et al.
European journal of biochemistry, 31(2), 230-233 (1972-12-04)
Ronit Avitsur et al.
Journal of leukocyte biology, 74(4), 507-513 (2003-09-10)
Stimulation of splenocytes from socially stressed mice [social disruption (SDR)] with Gram-negative bacterial lipopolysaccharide (LPS) revealed a state of functional glucocorticoid (GC) resistance. LPS-stimulated splenocytes were less sensitive to the inhibitory effects of corticosterone. This study demonstrated that activation signals
Progress in the synthesis and biological evaluation of lipid A and its derivatives
Gao J and Guo Z
Medicinal Research Reviews, 38(2), 556-601 (2018)
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Product Information Sheet - L5399

Product Information Sheet

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