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Merck

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

Número MDL:
Código UNSPSC:
12352211
ID de la sustancia en PubChem:
NACRES:
NA.25

origen biológico

Escherichia coli (F583 Rd mutant)

Nivel de calidad

Formulario

lyophilized powder

Condiciones de envío

ambient

temp. de almacenamiento

2-8°C

cadena SMILES

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)

Clave InChI

GZQKNULLWNGMCW-UHFFFAOYSA-N

Descripción general

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

Aplicación

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)

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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E E Ribi et al.
Journal of the National Cancer Institute, 55(5), 1253-1257 (1975-11-01)
A transplantable hepatocarcinoma of guinea pigs was used as an experimental model for immunotherapy of cancer. Earlier work showed that complete regression of 6- to 7-day-old tumors could be obtained in about 60% of cases by inoculation of the tumors
N Qureshi et al.
The Journal of biological chemistry, 257(19), 11808-11815 (1982-10-10)
Endotoxin extracted from the heptose-less mutant of Salmonella typhimurium was hydrolyzed in 0.1 N HCl in methanol/water (1:1, v/v) at 100 degrees C to yield lipid A, which was then fractionated on a Sephadex LH-20 column to yield a major
N Qureshi et al.
The Journal of biological chemistry, 258(21), 12947-12951 (1983-11-10)
Lipopolysaccharides extracted from the heptoseless mutant of Salmonella typhimurium G30/C21 were hydrolyzed with either 0.1 N HCl at 100 degrees C or treated twice with 20 mM sodium acetate, pH 4.5, at 100 degrees C for 45 min and finally
Characterization of the effects of endotoxin on macrophage tumor cell killing.
J B Weinberg et al.
Journal of immunology (Baltimore, Md. : 1950), 121(1), 72-80 (1978-07-01)
S Eperon et al.
Journal of immunological methods, 207(2), 135-145 (1997-11-22)
The aim of this study was to develop an in vitro test system for pyrogenic substances. Three clones derived from human monocytoid cell lines, which were selected by their high sensitivity to lipopolysaccharide (LPS), were assessed for tumor necrosis factor

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