(E)-C-HDMAPP (ammonium salt)

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).