2-amino-2-[2-(3-azido-4-octylphenyl)ethyl]propane-1,3-diol

FTY720 is a derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analog of sphingosine. It is a novel immune modulator that prolongs allograft transplant survival in numerous models by inhibiting lymphocyte emigration from lymphoid organs.¹ FTY720 is phosphorylated by sphingosine kinase, which then acts as a potent agonist at four of the sphingosine-1-phosphate (S1P) receptors (S1P₁, S1P₃, S1P₄, and S1P₅).² Down-regulation of S1P₁ receptors on T and B lymphocytes by FTY720 results in defective egress of these cells from spleen, lymph nodes, and Peyer’s patch.³ azido-FTY720 is a highly photoreactive analog of FTY720 that can be used to identify receptor binding sites for this ligand.⁴

1. Brinkmann, V., Pinschewer, D.D., Feng, L., et al. FTY720: Altered lymphocyte traffic results in allograft protection Transplantation 72(5),764-769(2001).
2. Brinkmann, V., Davis, M.D., Heise, C.E., et al. The immune modulator FTY720 targets sphingosine 1-phosphate receptors J. Biol. Chem. 277(24),21453-21457(2002).
3. Matloubian, M., Lo, C.G., Cinamon, G., et al. Lymphocyte egress from thymus and peripheral lymphoid organs is dependent on S1P receptor 1 Nature 427(6972),355-360(2004).
4. Sun, C., and Bittman, R. A photoreactive analogue of the immunosuppressant FTY720 J. Org. Chem. 71,2200-2202(2006).