A synthetic derivative of lipid A and a TLR4 agonist
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MPLA

Item No. 25998

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(3R)-3-hydroxytetradecanoate], 2-deoxy-6-O-[2-deoxy-3-O-[(3R)-1-oxo-3-[(1-oxotetradecyl)oxy]tetradecyl]-2-[[(3R)-1-oxo-3-[(1-oxotetradecyl)oxy]tetradecyl]amino]-4-O-phosphono-β-D-glucopyranosyl]-2-[[(3R)-3-hydroxy-1-oxotetradecyl]amino]-α-D-glucopyranose, monoammonium salt
CAS Number
1246298-63-4
Synonyms
  • Glucopyranosyl Lipid A
  • Monophosphoryl Lipid A
Molecular Formula
C96H180N2O22P • NH4
Formula Weight
1763.5
Formulation (Request formulation change)
A solution in sterile, double distilled water
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/ml
SMILES
OC[C@H]1O[C@@H](OC[C@H]2O[C@H](O)[C@H](NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](OC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H]2O)[C@H](NC(C[C@H](OC(CCCCCCCCCCCCC)=O)CCCCCCCCCCC)=O)[C@@H](OC(C[C@H](OC(CCCCCCCCCCCCC)=O)CCCCCCCCCCC)=O)[C@@H]1OP([O-])(O)=O.[NH4+]
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
InChi Key
UPAZUDUZKTYFBG-HNPUZVNISA-N
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

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    Product Description

    MPLA is a synthetic derivative of lipid A, a component of bacterial LPS, that is hexa-acylated in contrast to lipid A monophosphoryl from S. minnesota R595 (Item No. 25848), which can be hepta-, hexa-, or penta-acylated.1,2 MPLA is an agonist of toll-like receptor 4 (TLR4).2 Intramuscular injection of MPLA (5 μg/100 μl) in mice increases injection site transcription of MyD88- and TRIF-dependent genes as well as genes encoding cytokines and cytokine receptors, chemokines, and molecules involved in the complement pathway and antigen presentation.2 It also increases the number of CD3+ T cells and CD11c+ GR1+ dendritic cells recruited to draining lymph nodes and increases serum levels of CCL2/MCP-1, CXCL1, CSF3, IL-6, and IL-10 by more than 10-fold compared to control animals. Emulsions containing MPLA have demonstrated efficacy as vaccine adjuvants in several mouse models, enhancing immune responses to HIV gp140 antigen and providing protection against M. tuberculosis infection.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Qureshi, N., Mascagni, P., Ribi, E., et al. Monophosphoryl lipid A obtained from lipopolysaccharides of Salmonella minnesota R595. Purification of the dimethyl derivative by high performance liquid chromatography and complete structural determination. The Journal of Biological Chemisty 260(9), 5271-5278 (1985).

    2. Lambert, S.L., Yang, C.F., Liu, Z., et al. Molecular and cellular response profiles induced by the TLR4 agonist-based adjuvant Glucopyranosyl Lipid A. PLoS One 7(12), e51618 (2012).

    3. Arias, M.A., Van Roey, G.A., Tregoning, J.S., et al. Glucopyranosyl Lipid Adjuvant (GLA), a synthetic TLR4 agonist, promotes potent systemic and mucosal responses to intranasal immunization with HIVgp140. PLoS One 7(7), e41144 (2012).

    4. Baldwin, S.L., Bertholet, S., Reese, V.A., et al. The importance of adjuvant formulation in the development of a tuberculosis vaccine. J. Immunol. 188(5), 2189-2197 (2012).