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MPLA (PHAD?)

Monophosphoryl Lipid A (Synthetic) (PHAD®)

Vaccination is well-accepted as an effective method to prevent infections by mounting pathogen-specific immune responses prior to the infection. Usually, immunization with vaccine antigens alone is not able to induce robust or long-lasting immune responses — resulting in failure of protective immunity against infections. Thus, adjuvants are required to enhance cellular or humoral immune responses upon immunization. Because vaccine adjuvants using Lipid A have proven to be safe and effective in inducing Th-1 type immune responses to heterologous proteins in animal and human vaccines, Avanti developed Phosphorylated HexaAcyl Disaccharide (PHAD?), the first fully synthetic monophosphoryl Lipid A available for use as an adjuvant in human vaccines.

PHAD? is a synthetic structural analog of monophosphoryl Lipid A (MPLA) that has been shown to boost the immune system through activation of the toll-like receptor 4 (TLR4) resulting in production of proinflammatory cytokines and antigen-specific effector CD4+ and memory CD8+ T cells. Also referred to as GLA, this adjuvant has been administered to well over 1000 human subjects without serious adverse events. PHAD? is available in bulk quantities for vaccine development and commercial manufacturing.

Stimulatory effect of PHAD?, 3D-PHAD?, and 3D(6-acyl)-PHAD? on macrophages. Macrophage cell line J774 cells were cultured with Avanti PHAD?, 3D-PHAD?, or 3D(6-acyl)-PHAD? for 24hrs. IL-12 levels in supernatants were measured by sandwich ELISA.

Adjuvant Activity

PHAD?, 3D-PHAD?, and 3D(6A)-PHAD? have been tested extensively in animals using a variety of antigens. In all cases, these adjuvants exhibit a similar activity and safety profile to bacterially-derived MPL. The data above demonstrate the equivalency of the three synthetic adjuvants to the bacterially-derived MPL when presented in a liposomal carrier system (DMPC/DMPG/Cholesterol).

Data

Hygroscopic

No

Light Sensitive

No

Molecular Formula

C₉₆H₁₈₄N₃O₂₂P

Percent Composition

C 65.38%, H 10.52%, N 2.38% ,O 19.96%, P 1.76

Purity

> 99%

Stability

1 Years

Storage Temperature

-20°C

CAS Number

1246298-63-4 CAS Registry Number is a Registered Trademark of the American Chemical Society

FormulaWeight

1763.469

Exact Mass

1762.311

Synonyms

PHAD? phosphorylated hexaacyl disaccharideGlycopyranoside Lipid A (GLA)

Downloads

ChemDraw File
3D Structure
Structure
Brochure
699800 Adjuvant Data
Safety Data Sheet

References

Fisher BS, Dambrauskas N, Trakhimets O, Andrade DV, Smedley J, Sodora DL, Sather DN. Oral Immunization with HIV-1 Envelope SOSIP trimers elicits systemic immune responses and cross-reactive anti-V1V2 antibodies in non-human primates. PLoS One. 2020 May 29;15(5):e0233577. doi: 10.1371/journal.pone.0233577. PMID: 32470041; PMCID: PMC7259690.

PubMed ID: 32470041

Richard K, Perkins DJ, Harberts EM, Song Y, Gopalakrishnan A, Shirey KA, Lai W, Vlk A, Mahurkar A, Nallar S, Hawkins LD, Ernst RK, Vogel SN. Dissociation of TRIF bias and adjuvanticity. Vaccine. 2020 Jun 2;38(27):4298-4308. doi: 10.1016/j.vaccine.2020.04.042. Epub 2020 May 7. PMID: 32389496; PMCID: PMC7302928.

PubMed ID: 32389496

Boudousquié C, Boand V, Lingre E, Dutoit L, Balint K, Danilo M, Harari A, Gannon PO, Kandalaft LE. Development and Optimization of a GMP-Compliant Manufacturing Process for a Personalized Tumor Lysate Dendritic Cell Vaccine. Vaccines (Basel). 2020 Jan 14;8(1):E25. doi: 10.3390/vaccines8010025. PMID: 31947581.

PubMed ID: 31947581

Verma A, Schmidt BA, Elizaldi SR, Nguyen NK, Walter KA, Beck Z, Trinh HV, Dinsarapu AR, Lakshmanappa YS, Rane NN, Matyas GR, Rao M, Shen X, Tomaras GD, LaBranche CC, Reimann KA, Foehl DH, Gach JS, Forthal DN, Kozlowski PA, Amara RR, Iyer SS. Impact of Th1 CD4 TFH skewing on Antibody Responses to an HIV-1 Vaccine in Rhesus Macaques. J Virol. 2019 Dec 11;JVI.01737-19. doi: 10.1128/JVI.01737-19. [Epub ahead of print]. PMID: 31827000.

PubMed ID: 31827000

Wang L, Wang Z, Qin Y, Liang W. Delivered antigen peptides to resident CD8α+ DCs in lymph node by micelle-based vaccine augment antigen-specific CD8+ effector T cell response. Eur J Pharm Biopharm. 2020 Feb;147:76-86. doi: 10.1016/j.ejpb.2019.12.013. Epub 2019 Dec 28. PMID: 31887349.

PubMed ID: 31887349

Hernandez A, Luan L, Stothers CL, Patil NK, Fults JB, Fensterheim BA, Guo Y, Wang J, Sherwood ER, Bohannon JK. Phosphorylated Hexa-Acyl Disaccharides Augment Host Resistance Against Common Nosocomial Pathogens. Crit Care Med. 2019 Nov;47(11):e930-e938. doi: 10.1097/CCM.0000000000003967.

PubMed ID: 31567352

Maynard S, Marshall JD, MacGill RS, Yu L, Cann JA, Cheng LI, McCarthy MP, Cayatte C, Robbins SH. Vaccination with synthetic long peptide formulated with CpG in an oil-in-water emulsion induces robust E7-specific CD8 T cell responses and TC-1 tumor eradication. BMC Cancer. 2019 Jun 6;19(1):540. doi: 10.1186/s12885-019-5725-y.

PubMed ID: 31170937

Belnoue E, Mayol JF, Carboni S, Di Berardino Besson W, Dupuychaffray E, Nelde A, Stevanovic S, Santiago-Raber ML, Walker PR, Derouazi M. Targeting self and neo-epitopes with a modular self-adjuvanting cancer vaccine. JCI Insight. 2019 Apr 23;5. pii: 127305. doi: 10.1172/jci.insight.127305.

PubMed ID: 31013258

Zhao Z, Hu Y, Harmon T, Pentel P, Ehrich M, Zhang C. Effect of Adjuvant Release Rate on the Immunogenicity of Nanoparticle-Based Vaccines: A Case Study with a Nanoparticle-Based Nicotine Vaccine. Mol Pharm. 2019 Jun 3;16(6):2766-2775. doi: 10.1021/acs.molpharmaceut.9b00279. Epub 2019 May 22.

PubMed ID: 31075204

Liang T, Leung LM, Opene B, Fondrie WE, Lee YI, Chandler CE, Yoon SH, Doi Y, Ernst RK, Goodlett DR. Rapid microbial identification and antibiotic resistance detection by mass spectrometric analysis of membrane lipids. Anal Chem. 2018 Dec 20. doi: 10.1021/acs.analchem.8b02611. [Epub ahead of print]

PubMed ID: 30571097

Valencia S, Gill RB, Dowdell KC, Wang Y, Hornung R, Bowman JJ, Lacayo JC, Cohen JI. Comparison of vaccination with rhesus CMV (RhCMV) soluble gB with a RhCMV replication-defective virus deleted for MHC class I immune evasion genes in a RhCMV challenge model. Vaccine. 2019 Jan 7;37(2):333-342. doi: 10.1016/j.vaccine.2018.08.043. Epub 2018 Dec 3.

PubMed ID: 30522906

Jahan ST, Sadat SMA, Yarahmadi M, Haddadi A. Potentiating Antigen Specific Immune Response by Targeted Delivery of the PLGA-Based Model Cancer Vaccine. Mol Pharm. 2019 Feb 4;16(2):498-509. doi: 10.1021/acs.molpharmaceut.8b00700. Epub 2019 Jan 23.

PubMed ID: 30477303

Liang T, Leung LM, Opene B, Fondrie WE, Lee YI, Chandler CE, Yoon SH, Doi Y, Ernst RK, Goodlett DR. Rapid microbial identification and antibiotic resistance detection by mass spectrometric analysis of membrane lipids. Anal Chem. 2018 Dec 20. doi: 10.1021/acs.analchem.8b02611. [Epub ahead of print]

PubMed ID: 30571097

Lousada-Dietrich, S., Jogdand, P.S., Jepsen, S., Pinto, V.V., Ditlev, S.B., Christiansen, M., Larsen, S.O., Fox, C.B., Raman, V.S., Howard, R.F., Vedvick, T.S., Ireton, G., Carter, D., Reed, S.G., Theisen, M. (2011) A synthetic TLR4 agonist formulated in an emulsion enhances humoral and Type 1 cellular immune responses against GMZ2 - A GLURP-MSP3 fusion protein malaria vaccine candidate. Vaccine.

PubMed ID: 21349366

Coler, R.N., Bertholet, S., Moutaftsi, M., Guderian, J.A., Windish, H.P., Baldwin, S.L., Laughlin, E.M., Duthie, M.S., Fox, C.B., Carter, D., Friede, M., Vedvick, T.S., Reed, S.G. (2011) Development and characterization of synthetic glucopyranosyl lipid adjuvant system as a vaccine adjuvant. PLoS One. 6:e16333.

PubMed ID: 21298114

Anderson, R.C., Fox, C.B., Dutill, T.S., Shaverdian, N., Evers, T.L., Poshusta, G.R., Chesko, J., Coler, R.N., Friede, M., Reed, S.G., Vedvick, T.S. (2010) Physicochemical characterization and biological activity of synthetic TLR4 agonist formulations. Colloids Surf B Biointerfaces. 75:123-32.

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PubMed ID: 20593273

avanti polar lipids/MPLA (PHAD?)/1mg/699800P-1mg

699800 | MPLA (PHAD?)

Monophosphoryl Lipid A (Synthetic) (PHAD®)

MPLA (PHAD?)

Monophosphoryl Lipid A (Synthetic) (PHAD®)

Adjuvant Activity

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