Monophosphoryl lipid A - CAS# 1246298-63-4

Monophosphoryl lipid A (Glucopyranosyl lipid A) is a toll-like receptor 4 agonist. Monophosphoryl lipid A is derived from the cell wall of nonpathogenic Salmonella. Monophosphoryl lipid A can be used for the research of immunization and vaccine.

Product information

CAS Number: 1246298-63-4

Molecular Weight: 1763.47

Formula: C96H184N3O22P

Chemical Name: ammonium (2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6S)-3,6-dihydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]methoxy}-2-(hydroxymethyl)-5-[(3R)-3-(tetradecanoyloxy)tetradecanamido]-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl hydrogen phosphate

Smiles: [NH4+].CCCCCCCCCCC[C@H](CC(=O)O[C@H]1[C@H](OP([O-])(O)=O)[C@@H](CO)O[C@@H](OC[C@H]2O[C@H](O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)[C@@H]1NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC

InChiKey: UPAZUDUZKTYFBG-HNPUZVNISA-N

InChi: InChI=1S/C96H181N2O22P.H3N/c1-7-13-19-25-31-37-39-45-51-57-63-69-85(104)114-79(67-61-55-49-43-35-29-23-17-11-5)73-84(103)98-90-94(119-88(107)74-80(68-62-56-50-44-36-30-24-18-12-6)115-86(105)70-64-58-52-46-40-38-32-26-20-14-8-2)92(120-121(110,111)112)81(75-99)117-96(90)113-76-82-91(108)93(118-87(106)72-78(101)66-60-54-48-42-34-28-22-16-10-4)89(95(109)116-82)97-83(102)71-77(100)65-59-53-47-41-33-27-21-15-9-3;/h77-82,89-96,99-101,108-109H,7-76H2,1-6H3,(H,97,102)(H,98,103)(H2,110,111,112);1H3/t77-,78-,79-,80-,81-,82-,89-,90-,91-,92-,93-,94-,95+,96-;/m1./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Monophosphoryl lipid A (100 μg/ml, 2 hours; dendritic cells) induces NF-κB activation and modulates TLR2. Monophosphoryl lipid A (5~100 μg/ml, 24 hours; dendritic cells) induces IL-12 production by human. Increasing the amount of Monophosphoryl lipid A (from 0.1 to 1 μg), the percentage of matured BMDCs also increased. Monophosphoryl lipid A up-regulates dendritic cells surface markers. Monophosphoryl lipid A enhances T cell responses. Monophosphoryl lipid A (CD4 T cells) increases calcium mobilization of activated T cells.

In Vivo:

The generated Monophosphoryl lipid A has been shown to activate APC and to enhance the generation of both Th1- and Th2-specific immune response in mice.

Products are for research use only. Not for human use.