 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C96H184N3O22P |
| Molecular Weight | 1763.5008 |
| Exact Mass | 1762.31 |
| CAS # | 1246298-63-4 |
| PubChem CID | 134687617 |
| Appearance | White to off-white solid powder |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 22 |
| Rotatable Bond Count | 88 |
| Heavy Atom Count | 122 |
| Complexity | 2550 |
| Defined Atom Stereocenter Count | 14 |
| SMILES | CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O)NC(=O)C[C@@H](CCCCCCCCCCC)O)OC(=O)C[C@@H](CCCCCCCCCCC)O)O)CO)OP(=O)(O)[O-])OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC.[NH4+] |
| InChi Key | UPAZUDUZKTYFBG-HNPUZVNISA-N |
| InChi Code | 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 |
| Chemical Name | azanium;[(2R,3S,4R,5R,6R)-6-[[(2R,3S,4R,5R,6S)-3,6-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxyoxan-2-yl]methoxy]-2-(hydroxymethyl)-5-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-3-yl] hydrogen phosphate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Dendritic cells exposed to 100 μg/mL of monophosphoryl lipid A for two hours detect NF-κB activation and control TLR2 [2]. Human IL-12 production is induced by monophosphoryl lipid A (5~100 μg/mL, 24 hours; dendritic cells)[2]. When monophosphoryl lipid A is increased from 0.1 to 1 μg, the proportion of mature BMDCs likewise rises [1]. Dendritic cell surface markers are upregulated by monophosphoryl lipid A's action. Lipid A monophosphorylation improves T cell responses. Increases in monophosphoryl lipid A (CD4 T cells) stimulate calcium for T cells that have been activated [2]. |
| ln Vivo | It was established that the produced monophosphoester potentiometer A may activate APC and increase the development of Th1 and Th2 iodophor immunological responses in mice [2]. |
| Cell Assay |
Western Blot Analysis[2] Cell Types: dendritic cells Tested Concentrations: 100 μg/ml Incubation Duration: 2 hrs (hours) Experimental Results: Induces NF-κB activation and regulates TLR2. |
| References |
[1]. Recombination Monophosphoryl Lipid A-Derived Vacosome for the Development of Preventive Cancer Vaccines. ACS Appl Mater Interfaces. 2020;12(40):44554-44562. [2]. Monophosphoryl lipid A activates both human dendritic cells and T cells. J Immunol. 2002;168(2):926-932. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~25 mg/mL (~14.18 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (1.42 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.5671 mL | 2.8353 mL | 5.6705 mL | |
| 5 mM | 0.1134 mL | 0.5671 mL | 1.1341 mL | |
| 10 mM | 0.0567 mL | 0.2835 mL | 0.5671 mL |