 |  | | | | | (E)-C-HDMAPP (ammonium salt) | unclassified | | Reference 13151 |  |
| | | Data |  | CAS number | 933030-60-5 | | Molecular Formula | C6H14O7P2 · 3NH4 | | Formulation | A crystalline solid | | Purity | ≥95% | | Stability | 2 years | | Storage | -20°C | | Shipping | WET ICE | | Correlated Keywords | the, pyrophosphonate, form, of, (E)-HDMAPP;, much, more, stable, than, (E)-HDMAPP, in, solution, and, in, vascular, circulation;, potently, stimulates, the, synthesis, of, TNF-α, by, γδ-T, lymphocytes, with, an, IC50, of, 0.91, nM;, also, significantly, increases, the, number, of, circulating, γδ-T, cells, in, vivo | | Synonyms | (E)-1-Hydroxy-2-Methylbut-2-enyl 4-Diphosphate (ammonium salt) |
| | | Description | Synthetic and natural alkyl phosphates, also known as phosphoantigens, stimulate the proliferation of γδ-T lymphocytes. Isopentenyl pyrophosphate, and related derivatives including (E)-hydroxy-dimethyl-allyl pyrophosphate ((E)-HDMAPP), are particularly effective activators of γδ-T cells. (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. (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. (E)-C-HDMAPP also significantly increases the number of circulating γδ-T cells in vivo, in cynomolgus monkeys. | | | Related Products | | | | Documentation | | | | | | Tanaka, Y., Sano, S., Nieves, E., et al. Nonpeptide ligands for humanγδT cells. Proc Natl Acad Sci USA 91 8175-8179 (1994). | | Poupot, M., Fournié, J. Non-peptide antigens activating human Vg9/Vd2 T lymphocytes. Immunol Lett 95 129-138 (2004). | | Tanaka, Y., Morita, C.T., Tanaka, Y., et al. Natural and synthetic non-peptide antigens recognized by humanγδT cells. Nature 375 155-158 (1995). | | 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 1747-1754 (2008). |
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