Monophosphoryl lipid A

• CAT Number: I032738
• CAS Number: 1246298-63-4
• Molecular Formula: C96H184N3O22P
• Molecular Weight: 1763.47
• Purity: ≥95%
• Synonyms: 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
• 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
• InChIKey: UPAZUDUZKTYFBG-HNPUZVNISA-N
• SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)NC1C(C(C(OC1OCC2C(C(C(C(O2)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)CO)OP(=O)(O)[O-])OC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC.[NH4+]

Monophosphoryl lipid A (Cat No.: I032738) is a detoxified derivative of lipid A, the bioactive component of lipopolysaccharide (LPS) from Gram-negative bacteria. It retains immunostimulatory properties through Toll-like receptor 4 (TLR4) activation but with greatly reduced toxicity compared to native lipid A. MPLA is widely used as a vaccine adjuvant to enhance both humoral and cellular immune responses. It promotes antigen-specific immunity while minimizing inflammatory side effects, making it valuable in prophylactic and therapeutic vaccine formulations for infectious diseases, cancer, and immunotherapy research.

Reference

[1]. Cheng R, et al. Recombination Monophosphoryl Lipid A-Derived Vacosome for the Development of Preventive Cancer Vaccines. ACS Appl Mater Interfaces. 2020;12(40):44554-44562.
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[2]. Ismaili J, et al. Monophosphoryl lipid A activates both human dendritic cells and T cells. J Immunol. 2002;168(2):926-932.
[Content Brief]