| Identification | Back Directory | [Name]
(E)-C-HDMAPP (ammonium salt) | [CAS]
933030-60-5 | [Synonyms]
(E)-C-HDMAPP (ammonium salt)
(E)-C-HDMAPP (ammonium salt) Exclusive
triazanium:[(E)-5-hydroxy-4-methylpent-3-enyl]-phosphonatooxyphosphinate | [Molecular Formula]
C6H17NO7P2 | [MDL Number]
MFCD18428007 | [MOL File]
933030-60-5.mol | [Molecular Weight]
277.15 |
| Hazard Information | Back Directory | [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 | [Uses]
(E)-C-HDMAPP (Ammonium Salt) is a useful research chemical compound used in the preparation of phosphoantigen salts of organic bases and methods for their crystallization. | [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. Bo?dec, 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). |
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