Activator of γδ-T-lymphocytes
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Product Type

Biochemicals

Research Area

Immunology & Inflammation
Adaptive Immunity

(E)-C-HDMAPP (ammonium salt)

Item No. 13151

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
P’-[(3E)-5-hydroxy-4-methyl-3-penten-1-yl]-isohypophosphoric acid, triammonium salt
CAS Number
933030-60-5
Synonyms
  • (E)-5-hydroxy-4-methylpent-3-enyl pyrophosphate
Molecular Formula
C6H14O7P2 • 3NH4
Formula Weight
311.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
[O-]P(OP([O-])(CC/C=C(CO)\C)=O)([O-])=O.[NH4+].[NH4+].[NH4+]
InChi Code
InChI=1S/C6H14O7P2.3H3N/c1-6(5-7)3-2-4-14(8,9)13-15(10,11)12;;;/h3,7H,2,4-5H2,1H3,(H,8,9)(H2,10,11,12);3*1H3/b6-3+;;;
InChi Key
VLHWKNAWRGFXCI-LESCHLGKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $84

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    1 mg

    $159

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    5 mg

    $665

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    10 mg

    $1,081

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    Product Description

    Synthetic and natural alkyl phosphates, also known as phosphoantigens, stimulate the proliferation of γδ-T lymphocytes.1 Isopentenyl pyrophosphate, and related derivatives including (E)-hydroxy-dimethyl-allyl pyrophosphate ((E)-HDMAPP), are particularly effective activators of γδ-T cells.2,3 (E)-C-HDMAPP is the pyrophosphonate form of (E)-HDMAPP. The pyrophosphonate moiety in (E)-C-HDMAPP is much less susceptible to chemical or enzymatic hydrolysis than its pyrophosphate counterpart. As a result, (E)-C-HDMAPP is much more stable in solution and in vascular circulation.4 (E)-C-HDMAPP possesses comparable activity to (E)-HDMAPP, which is the most potent of the isoprenoid phosphoantigens. (E)-C-HDMAPP stimulates the synthesis of tumor necrosis factor (TNF-α) by γδ-T lymphocytes with an IC50 value of 0.91 nM.4 (E)-C-HDMAPP also significantly increases the number of circulating γδ-T cells in vivo, in cynomolgus monkeys.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tanaka, Y., Sano, S., Nieves, E., et al. Nonpeptide ligands for human γδ T cells. Proc. Natl. Acad. Sci. USA 91(17), 8175-8179 (1994).

    2. Poupot, M., and Fournié, J.J. Non-peptide antigens activating human Vγ9/Vδ2 T lymphocytes. Immunol. Lett. 95(2), 129-138 (2004).

    3. Tanaka, Y., Morita, C.T., Tanaka, Y., et al. Natural and synthetic non-peptide antigens recognized by human γδ T cells. Nature 375(6527), 155-158 (1995).

    4. Boëdec, A., Sicard, H., Dessolin, J., et al. Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate. J. Med. Chem. 51(6), 1747-1754 (2008).