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FTY720 (S)-Phosphate

Cayman Chemical Item Number 10006408

(S)-FTY 720P (CAS 402616-26-6)

FTY720 (S)-Phosphate (CAS 402616-26-6)

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Description

FTY720 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 kinases in vivo, and then acts as a potent agonist at four of the five sphingosine-1-phosphate (S1P) receptors.2 FTY720 (S)-phosphate is the single stereoisomer formed by phosphorylation of FTY720 in vivo, as determined in rats and humans.3 It exhibits Ki values of 2.1, 5.9, 23, and 2.2 nM for S1P1,3,4,5, respectively, whereas the R enantiomer binds with 5 to 130-fold lower affinity.4 FTY720 (S)-phosphate causes internalization of S1P1 on lymphocytes, abrogating S1P-dependent egress of lymphocytes from lymphoid organs.5 It also enhances endothelial barrier function,5 stimulates the activity of the sphingosine transporter Abcb1 and the leukotriene C4 transporter Abcc16 and inhibits cytosolic phospholipase A2 activity.7

1 Brinkmann, V., Pinschewer, D.D., Feng, L., et al. FTY720: Altered lymphocyte traffic results in allograft protection. Transplantation 72 764-769 (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 Albert, R., Hinterding, K., Brinkmann, V., et al. Novel immunomodulator FTY720 is phosphorylated in rats and humans to form a single stereoisomer. Identification, chemical proof, and biological characterization of the biologically active species and its enantiomer. J Med Chem 48 5373-5377 (2005).

4 Kiuchi, M., Adachi, K., Tomatsu, A., et al. Asymmetric synthesis and biological evaluation of the enantiomeric isomers of the immunosuppressive FTY720-phosphate. Bioorg Med Chem 13 425-432 (2005).

5 Brinkmann, V. FTY720: Mechanism of action and potential benefit in organ transplantation. Yonsei Med J 45(6) 991-997 (2004).

6 Honig, S.M., Fu, S., Mao, X., et al. FTY720 stimulates multidrug transporter- and cysteinyl leukotriene-dependent T cell chemotaxis to lymph nodes. J Clin Invest 111(5) 627-637 (2003).

7 Payne, S.G., Oskeritizian, C.A., Griffiths, R., et al. The immunosuppressant drug FTY720 inhibits cytosolic phospholipase A2 independently of sphingosine-1-phosphate receptors. Blood 109(3) 1077-1085 (2007).

Synonyms
  • (S)-FTY 720P
Formal Name (2S)-​amino-​2-​[2-​(4-​octylphenyl)ethyl]-​1-​(dihydrogen phosphate)-​1,​3-​propanediol
CAS Number 402616-26-6
Molecular Formula C19H34NO5P
Formula Weight 387.5
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCCCCc1ccc(cc1)​CC[C@]​(N)​(CO)​COP(=O)​(O)​O

Background Reading

Brinkmann, V. FTY720: Mechanism of action and potential benefit in organ transplantation. Yonsei Med J 45(6) 991-997 (2004).

Brinkmann, V., Pinschewer, D.D., Feng, L., et al. FTY720: Altered lymphocyte traffic results in allograft protection. Transplantation 72 764-769 (2001).

Size Price Quantity Subtotal
500 µg $56.00 $0.00
1 mg $106.00 $0.00
5 mg $448.00 $0.00
10 mg $784.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-05-25. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

Related Products

FTY720
FTY720 Phosphate
FTY720 (R)-Phosphate Exclusive
Sphingosine-1-Phosphate
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