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L5399

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

Name: Lipid A, diphosphoryl from <I>Escherichia coli</I> F583 (Rd mutant)
Brand: SIGMA

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MDL number:

MFCD00131510

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tumor regression caused by endotoxins and mycobacterial fractions.

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

Purification and structural determination of nontoxic lipid A obtained from the lipopolysaccharide of Salmonella typhimurium.

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

Position of ester groups in the lipid A backbone of lipopolysaccharides obtained from Salmonella typhimurium.

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)

Human monocytoid cell lines as indicators of endotoxin: comparison with rabbit pyrogen and Limulus amoebocyte lysate assay.

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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