MPLA | CAS#1246298-63-4 |TLR4 agonist

MedKoo Cat#: 412663 | Name: MPLA

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Monophosphoryl lipid A (MPLA) is a natural agonist for the toll-like receptor-4 (TLR4). It is useful as an adjuvant in immunization. MPLA is a safe prophylactic agent and has immunotherapeutic applications. MPLA used in vaccination improves B cell and T cell-mediated immunity.

Chemical Structure

MPLA

CAS#1246298-63-4

Theoretical Analysis

MedKoo Cat#: 412663

Name: MPLA

CAS#: 1246298-63-4

Chemical Formula: C96H184N3O22P

Exact Mass:

Molecular Weight: 1763.50

Elemental Analysis: C, 65.38; H, 10.52; N, 2.38; O, 19.96; P, 1.76

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

GLA-SE; MPLA; PHAD®; phosphorylated hexaacyl disaccharide; Glycopyranoside Lipid A (GLA)

IUPAC/Chemical Name

ammonium (2R,3S,4R,5R,6R)-6-(((2R,3S,4R,5R,6S)-3,6-dihydroxy-5-((R)-3-hydroxytetradecanamido)-4-(((R)-3-hydroxytetradecanoyl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-2-(hydroxymethyl)-5-((R)-3-(tetradecanoyloxy)tetradecanamido)-4-(((R)-3-(tetradecanoyloxy)tetradecanoyl)oxy)tetrahydro-2H-pyran-3-yl hydrogen phosphate

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,763.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Wed Dec 09 10:59:15 2020 Search: Monophosphoryl lipid A 20 selected items PubMed Results Items 1-20 of 20 (Display the 20 citations in PubMed) 1: de Castro JC, de Almeida LV, Cardoso MS, Oliveira FMS, Nogueira DS, Reis- Cunha JL, Magalhaes LMD, Zhan B, Bottazzi ME, Hotez PJ, Bueno LL, Bartholomeu DC, Fujiwara RT. Vaccination with chimeric protein induces protection in murine model against ascariasis. Vaccine. 2020 Nov 26:S0264-410X(20)31499-7. doi: 10.1016/j.vaccine.2020.11.046. Epub ahead of print. PMID: 33248854. 2: Tsuruoka S, Purkerson JM, Schwartz GJ. Lipopolysaccharide directly inhibits bicarbonate absorption by the renal outer medullary collecting duct. Sci Rep. 2020 Nov 25;10(1):20548. doi: 10.1038/s41598-020-77363-w. PMID: 33239624; PMCID: PMC7689453. 3: Li JB, Li JJ, Li M, Gao C, Zhang L, Li M, Zhu Q. Oral immunization induces a novel CXCR6+ β7+ intraepithelial lymphocyte subset predominating in the small intestine. Scand J Immunol. 2020 Nov 17:e12996. doi: 10.1111/sji.12996. Epub ahead of print. PMID: 33205443. 4: Wang YQ, Bazin-Lee H, Evans JT, Casella CR, Mitchell TC. MPL Adjuvant Contains Competitive Antagonists of Human TLR4. Front Immunol. 2020 Oct 16;11:577823. doi: 10.3389/fimmu.2020.577823. PMID: 33178204; PMCID: PMC7596181. 5: Kim WS, Zhi Y, Guo H, Byun EB, Lim JH, Seo HS. Promotion of Cellular and Humoral Immunity against Foot-and-Mouth Disease Virus by Immunization with Virus-Like Particles Encapsulated in Monophosphoryl Lipid A and Liposomes. Vaccines (Basel). 2020 Oct 31;8(4):633. doi: 10.3390/vaccines8040633. PMID: 33142799; PMCID: PMC7712044. 6: Mahler V, Kleine-Tebbe J, Vieths S. Immuntherapien von Allergien: Aktueller Stand [Immunotherapy of allergies: current status]. Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz. 2020 Nov;63(11):1341-1356. German. doi: 10.1007/s00103-020-03224-6. Epub 2020 Nov 2. PMID: 33140209; PMCID: PMC7647996. 7: Alarcón-Vila C, Baroja-Mazo A, de Torre-Minguela C, Martínez CM, Martínez- García JJ, Martínez-Banaclocha H, García-Palenciano C, Pelegrin P. CD14 release induced by P2X7 receptor restricts inflammation and increases survival during sepsis. Elife. 2020 Nov 2;9:e60849. doi: 10.7554/eLife.60849. PMID: 33135636; PMCID: PMC7690950. 8: Hao L, Wu Y, Zhang Y, Zhou Z, Lei Q, Ullah N, Banga Ndzouboukou JL, Lin X, Fan X. Combinational PRR Agonists in Liposomal Adjuvant Enhances Immunogenicity and Protective Efficacy in a Tuberculosis Subunit Vaccine. Front Immunol. 2020 Sep 30;11:575504. doi: 10.3389/fimmu.2020.575504. PMID: 33117374; PMCID: PMC7561437. 9: Verpalen ECJM, Brouwer AJ, Boons GJ. Synthesis of monophosphoryl lipid A using 2-naphtylmethyl ethers as permanent protecting groups. Carbohydr Res. 2020 Sep 25;498:108152. doi: 10.1016/j.carres.2020.108152. Epub ahead of print. PMID: 33032087. 10: Francis JE, Skakic I, Dekiwadia C, Shukla R, Taki AC, Walduck A, Smooker PM. Solid Lipid Nanoparticle Carrier Platform Containing Synthetic TLR4 Agonist Mediates Non-Viral DNA Vaccine Delivery. Vaccines (Basel). 2020 Sep 21;8(3):551. doi: 10.3390/vaccines8030551. PMID: 32967285; PMCID: PMC7563538. 11: Cheng R, Fontana F, Xiao J, Liu Z, Figueiredo P, Shahbazi MA, Wang S, Jin J, Torrieri G, Hirvonen JT, Zhang H, Chen T, Cui W, Lu Y, Santos HA. Recombination Monophosphoryl Lipid A-Derived Vacosome for the Development of Preventive Cancer Vaccines. ACS Appl Mater Interfaces. 2020 Oct 7;12(40):44554-44562. doi: 10.1021/acsami.0c15057. Epub 2020 Sep 22. PMID: 32960566; PMCID: PMC7549091. 12: Ullah N, Hao L, Wu Y, Zhang Y, Lei Q, Banga Ndzouboukou JL, Lin X, Fan X. Differential Immunogenicity and Protective Efficacy Elicited by MTO- and DMT- Adjuvanted CMFO Subunit Vaccines against Mycobacterium tuberculosis Infection. J Immunol Res. 2020 Sep 4;2020:2083793. doi: 10.1155/2020/2083793. PMID: 32953889; PMCID: PMC7487112. 13: Tukhvatulin A, Dzharullaeva A, Erokhova A, Zemskaya A, Balyasin M, Ozharovskaia T, Zubkova O, Shevlyagina N, Zhukhovitsky V, Fedyakina I, Pruss I, Shcheblyakov D, Naroditsky B, Logunov D, Gintsburg A. Adjuvantation of an Influenza Hemagglutinin Antigen with TLR4 and NOD2 Agonists Encapsulated in Poly(D,L-Lactide-Co-Glycolide) Nanoparticles Enhances Immunogenicity and Protection against Lethal Influenza Virus Infection in Mice. Vaccines (Basel). 2020 Sep 10;8(3):519. doi: 10.3390/vaccines8030519. PMID: 32927915; PMCID: PMC7564367. 14: Zhang W, Lim SM, Hwang J, Ramalingam S, Kim M, Jin JO. Monophosphoryl lipid A-induced activation of plasmacytoid dendritic cells enhances the anti-cancer effects of anti-PD-L1 antibodies. Cancer Immunol Immunother. 2020 Sep 9. doi: 10.1007/s00262-020-02715-4. Epub ahead of print. PMID: 32902663. 15: Alzhrani RF, Xu H, Valdes SA, Cui Z. Intranasal delivery of a nicotine vaccine candidate induces antibodies in mouse blood and lung mucosal secretions that specifically neutralize nicotine. Drug Dev Ind Pharm. 2020 Oct;46(10):1656-1664. doi: 10.1080/03639045.2020.1820033. Epub 2020 Sep 15. PMID: 32892651. 16: Mabrouk MT, Huang WC, Deng B, Li-Purcell N, Seffouh A, Ortega J, Ekin Atilla-Gokcumen G, Long CA, Miura K, Lovell JF. Lyophilized, antigen-bound liposomes with reduced MPLA and enhanced thermostability. Int J Pharm. 2020 Sep 2;589:119843. doi: 10.1016/j.ijpharm.2020.119843. Epub ahead of print. PMID: 32890653. 17: Techawiwattanaboon T, Barnier-Quer C, Palaga T, Jacquet A, Collin N, Sangjun N, Komanee P, Patarakul K. A Comparison of Intramuscular and Subcutaneous Administration of LigA Subunit Vaccine Adjuvanted with Neutral Liposomal Formulation Containing Monophosphoryl Lipid A and QS21. Vaccines (Basel). 2020 Sep 1;8(3):494. doi: 10.3390/vaccines8030494. PMID: 32882903; PMCID: PMC7565420. 18: Om K, Paquin-Proulx D, Montero M, Peachman K, Shen X, Wieczorek L, Beck Z, Weiner JA, Kim D, Li Y, Mdluli T, Shubin Z, Bryant C, Sharma V, Tokarev A, Dawson P, White Y, Appelbe O, Klatt NR, Tovanabutra S, Estes JD, Matyas GR, Ferrari G, Alving CR, Tomaras GD, Ackerman ME, Michael NL, Robb ML, Polonis V, Rolland M, Eller MA, Rao M, Bolton DL. Adjuvanted HIV-1 vaccine promotes antibody-dependent phagocytic responses and protects against heterologous SHIV challenge. PLoS Pathog. 2020 Sep 3;16(9):e1008764. doi: 10.1371/journal.ppat.1008764. PMID: 32881968; PMCID: PMC7505435. 19: Azimi A, Heidarian S, Zamani H, Taleghani N, Dehghani M, Seyedjafari E. Optimized dose of synthetic analogues of Monophosphoryl lipid A as an effective alternative for formulating recombinant human papillomavirus vaccine. Biologicals. 2020 Nov;68:60-64. doi: 10.1016/j.biologicals.2020.08.007. Epub 2020 Aug 25. PMID: 32859464. 20: Huang WC, Deng B, Mabrouk MT, Seffouh A, Ortega J, Long C, Miura K, Wu Y, Lovell JF. Particle-based, Pfs230 and Pfs25 immunization is effective, but not improved by duplexing at fixed total antigen dose. Malar J. 2020 Aug 28;19(1):309. doi: 10.1186/s12936-020-03368-5. PMID: 32859199; PMCID: PMC7453371.