FTY720 (S)-PhosphateCAS: 402616-26-6
MF: C19H34NO5P
MW: 387.45
A potent agonist for EDG-1, -3, -4 and -5.

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

FTY720 (S)-Phosphate | CAS 402616-26-6 is rated 5.0 out of 5 by 1.
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Synonym: (2S)- amino-2-[2-(4-octylphenyl)ethyl]-1-(dihydrogen phosphate)-1,3-propanediol
Application: A potent agonist for EDG-1, -3, -4 and -5
CAS Number: 402616-26-6
Purity: ≥98%
Molecular Weight: 387.45
Molecular Formula: C19H34NO5P
* Refer to Certificate of Analysis for lot specific data (including water content).
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FTY720 (S)-Phosphate is a novel immune modulator that prolongs allograft transplant survival in numerous models by inhibiting lymphocyte emigration from lymphoid organs. Phosphorylated by sphingosine kinases in vivo, FTY720 then acts as a potent agonist at EDG-1, EDG-3, EDG-4 and EDG-5 (Endothelial differential gene). FTY720 (S)-phosphate is the single stereoisomer formed by phosphorylation of FTY720 in vivo, as determined in rats and humans. It exhibits Ki values of 2.1, 5.9, 23, and 2.2 nM for EDG-1,-3,-4 and -5, respectively, whereas the R enantiomer binds with 5-130-fold lower affinity. FTY720 (S)-phosphate causes internalization of S1P1 on lymphocytes, abrogating S1P-dependent egress of lymphocytes from lymphoid organs. It also enhances endothelial barrier function, stimulates the activity of the sphingosine transporter Abcb1 and the leukotriene C4 transporter Abcc16 and inhibits cytosolic phospholipase A2 activity.


References

1. Brinkmann, V., et al. 2001. Transplantation. 72: 764-769. PMID: 11571432
2. Brinkmann, V., et al. 2002. J. Biol. Chem. 277: 21453-21457. PMID: 11967257
3. Albert, R., et al. 2005. J. Med Chem. 48: 5373-5377. PMID: 16078855
4. Kiuchi, M., et al. 2005. Bioorg. Med. Chem. 13: 425-432. PMID: 15598563
5. Brinkmann, V. 2004. Yonsei Med. J. 45: 991-997. PMID: 15627289
6. Honig, S.M., et al. 2003. J. Clin. Invest. 111: 627-637. PMID: 12618517
7. Payne, S.G., et al. Blood. 109: 1077-1085. PMID: 17008548

Physical State :
Solid
Solubility :
Soluble in chloroform (~0.5 mg/ml), DMSO, and methanol (sparingly). Insoluble in water(at 25° C).
Storage :
Store at -20° C
Melting Point :
195-198° C
Boiling Point :
584.24° C at 760 mmHg (Predicted)
Density :
1.17 g/cm3 (Predicted)
Refractive Index :
n20D 1.54 (Predicted)
IC50 :
EDG-1: IC50 = 0.28 nM (human); EDG-6: IC50 = 2.2 nM (human); EDG-5: IC50 = 5.9 nM (human); EDG-3: IC50 = 6.3 nM (human)
Ki Data :
SIP1: Ki= 2.1 nM; SIP5: Ki= 2.2 nM; SIP3: Ki= 5.9 nM; SIP4: Ki= 23 nM
pK Values :
pKa: 1.73 (Predicted), pKb: 10.04 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
11452022
MDL Number :
MFCD09840646
SMILES :
CCCCCCCCC1=CC=C(C=C1)CC[C@](CO)(COP(=O)(O)O)N

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Certificate of Analysis

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FTY720 (S)-Phosphate  Product Citations

See how others have used FTY720 (S)-Phosphate. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 26216939  Skrzeczyńska-Moncznik, J. et al. 2015. J. Leukoc. Biol. 98: 591-9.

PMID: # 16549044  Chiba, K. et al. 2006. Cell. Mol. Immunol. 3: 11-19.

PMID: # 15808561  Chiba, K. et al. 2005 Jan-Feb. Transplant. Proc. 37: 102-106.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Chiba et al Chiba et al. (Pubmed 15808561) reported that when rats with skin allografts were treated with FTY720 (S)-Phosphate intravenously significantly increased immune suppression and prolonged the allograft viability. -SCBT Publication Review
Date published: 2015-01-20
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