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Merck
CN

699852P

Avanti

3D-PHAD™

Avanti Research™ - A Croda Brand

Synonym(s):

Monophosphoryl 3-Deacyl Lipid A (Synthetic) Pat No. 9,241,988

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About This Item

Empirical Formula (Hill Notation):
C82H158N3O20P
CAS Number:
1699735-79-9
Molecular Weight:
1537.11
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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InChI

1S/C82H155N2O20P.H3N/c1-6-11-16-21-26-31-33-38-43-48-53-58-72(89)99-66(56-51-46-41-36-29-24-19-14-9-4)61-71(88)84-76-80(103-74(91)62-67(57-52-47-42-37-30-25-20-15-10-5)100-73(90)59-54-49-44-39-34-32-27-22-17-12-7-2)79(104-105(95,96)97)68(63-85)102-82(76)9

InChI key

XERJCJBCCDONJL-WOBTUNBLSA-N

SMILES string

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]2O.[NH4+]

assay

>99% (HPLC)

form

powder

packaging

pkg of 1 × 1 mg (699852P-1mg), pkg of 1 × 5 mg (699852P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

application(s)

vaccine development

shipped in

dry ice

storage temp.

−20°C

General description

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.

Application

3D-PHAD™ has been used:
  • as a synthetic adjuvant for respiratory syncytial virus (RSV) vaccine
  • as a synthetic adjuvant to prepare hepatitis B virus (HBV) and virus-like particles (VLP)-based human papillomavirus (HPV) vaccines
  • in liposome preparation for the generation of army liposome formulation (ALF) for human immunodeficiency (HIV) gp140 antigen immunization studies in mice.

Biochem/physiol Actions

3-deacyl-phosphorylated hexa-acyl disaccharide (3D-PHAD™) is derived from monophosphoryl lipid A. It is amphiphilic and associates with the virosomal membranes.

Features and Benefits

The highly pure MPLA analog, 3D-PHAD™, provides a homogeneous synthetic equivalent for the 3-deacylated MPLA derived from bacterial LPS. 3D-PHAD™ is less pyrogenic than its bacterial-derived mimic while eliciting a comparable response to other MPLA analogs.

Packaging

2 mL Amber Glass Crimp Cap Vial (699852P-1mg)
2 mL Amber Glass Crimp Cap Vial (699852P-5mg)

Other Notes

For R&D use only. Not for drug, household, or other uses.

Legal Information

3D-PHAD is a trademark of Avanti Polar Lipids, LLC
Avanti Research is a trademark of Avanti Polar Lipids, LLC
PHAD is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Immune response to antigen adsorbed to aluminum hydroxide particles: Effects of co-adsorption of ALF or ALFQ adjuvant to the aluminum-antigen complex
Beck Z, et al.
Journal of Controlled Release : Official Journal of the Controlled Release Society, 275, 1219-1219 (2018)
Monica L Martin et al.
Malaria journal, 18(1), 377-377 (2019-11-30)
Indian-origin rhesus (InR) are preferred for research, but strict export restrictions continue to limit their use. Chinese-origin rhesus (ChR), although easier to procure, are genetically distinct from InR and differ in their immune response to infectious agents, such as the
Immunogenicity of HPV and HBV vaccines: adjuvanticity of synthetic analogs of monophosphoryl lipid A combined with aluminum hydroxide
Taleghani N, et al.
Acta Pathologica, Microbiologica et Immunological Scandinavica, 127(3), 150-157 (2019)
Development of a virosomal RSV vaccine containing 3D-PHAD Adjuvant: formulation, composition, and long-term stability
Lederhofer J
Pharmaceutical Research, 35(9), 172-172 (2018)

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