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L5399

Sigma-Aldrich

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

Sinónimos:

Diphosphoryl Lipid A from E.Coli.

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About This Item

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

biological source

Escherichia coli (F583 Rd mutant)

Quality Level

200

form

lyophilized powder

shipped in

ambient

storage temp.

2-8°C

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)

InChI key

GZQKNULLWNGMCW-UHFFFAOYSA-N

General description

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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E E Ribi et al.
Cancer research, 39(11), 4756-4759 (1979-11-01)
We described elsewhere that the synergistic antitumor activity of endotoxic extracts from Re mutants of gram-negative bacteria and trehalose mycolate against guinea pig syngeneic line 10 tumor was abrogated after peptide substances accompanying these extracts had been removed. This activity
C B Louise et al.
Infection and immunity, 60(4), 1536-1543 (1992-04-01)
This study explores the in vitro relationship between Shiga toxin-producing Shigella spp. and Escherichia coli and the development of vascular complications in humans following bacillary dysentery. We propose that lipopolysaccharide (LPS; endotoxin) may combine with Shiga toxin to facilitate vascular
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)
Activation of complement by endotoxin.
S E Mergenhagen et al.
The Journal of infectious diseases, 128, Suppl:86-Suppl:90 (1973-07-01)
A Carlsson et al.
Microbiology (Reading, England), 144 ( Pt 8), 2179-2188 (1998-08-28)
Attacin is a 20 kDa antibacterial protein, originally isolated from the immune haemolymph of Hyalophora cecropia. It has been demonstrated previously that attacin causes increased permeability of the outer membrane of Escherichia coli and inhibition of outer-membrane protein synthesis at
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