NBD-FTY720 phenoxy (hydrochloride)

Cayman Chemical Item Number 16841

NBD-FTY720 phenoxy (hydrochloride)

Description

FTY720 is an immune modulator that down-regulates sphingosine-1-phosphate (S1P) receptors,¹ enhances the activity of the sphingosine transporter Abcb1 and the leukotriene C₄ transporter Abcc1,² and inhibits cytosolic phospholipase A₂ activity.³ It is known that some of the effects of FTY720 require its phosphorylation by sphingosine kinases in vivo, with FTY720-phosphate binding to and down-regulating S1P receptors. NBD-FTY720 is a fluorescently-labeled analog of FTY720. The hydroxy methyl side chain of FTY720 that is targeted for phosphorylation by sphingosine kinases is retained in this analog, suggesting that it would likewise be phosphorylated in vivo.

1 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).

2 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).

3 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).

Formal Name

N-[2R-hydroxy-1R-(hydroxymethyl)-3E-heptadecenyl]-2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol,monohydrochloride

Molecular Formula

C₂₃H₃₁N₅O₆ · HCl

Formula Weight

510.0

Formulation

A solution in methanol:chloroform (1:1)

Purity

≥96%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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OCC(N)(CO)CCc1ccc(OCCCCCCNc2ccc([N](=O)O)c3nonc23)cc1

Background Reading

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).

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).

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).

Size

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Subtotal

100 µg 
$26.00

$0.00

500 µg 
$117.00

$0.00

1 mg 
$208.00

$0.00

5 mg 
$910.00

$0.00

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$0.00

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NBD-FTY720 phenoxy (hydrochloride)