402615-91-2 Usage
Uses
Used in Pharmaceutical Industry:
racFTY720 Phosphate is used as a therapeutic agent for the treatment of autoimmune diseases, particularly experimental autoimmune encephalomyelitis (EAE). It functions by inhibiting T cell infiltration, which helps in reducing the severity and progression of the disease.
Used in Research Applications:
In addition to its therapeutic use, racFTY720 Phosphate is also employed as a research tool in the field of immunology and cell biology. It aids in understanding the role of sphingosine 1-phosphate receptors in various cellular processes and their potential as targets for drug development.
Used in Drug Development:
racFTY720 Phosphate serves as a lead compound in the development of new drugs targeting sphingosine 1-phosphate receptors. Its unique properties and interactions with these receptors make it a valuable starting point for designing and synthesizing novel therapeutic agents with improved efficacy and selectivity.
Biological Activity
fty720 is sphingosine-1-phosphate (s1p) receptors agonist [1]. fty720 is a novel immunomodulatory agent derived from isp-1 (myriocin), a fungal metabolite that exists in traditional chinese herbal medicine. in higher eukaryotes, s1p is the ligand for five g-protein-coupled receptors. these s1p receptors are differentially expressed and regulate vascular maturation, angiogenesis, cardiac development and immunity. s1p receptors are important for directed cell movement [2].
in vitro
the phosphorylated fty720 acted as agonist for a family of g protein-coupled receptors in vitro. fty720 inhibited sphingosine-1-phosphate lyase activity [3]. fty720 phosphate acted as a potent agonist at sphingosine-1-phosphate (s1p) receptors s1p1, s1p3, s1p4, and s1p5 with ic50 values of 0.2-6 nm [3].
in vivo
in a variety of transplant and autoimmune models, fty720 was efficacious without inducing a generalized immunosuppressed state. fty720 was effective in human kidney transplantation. fty720 elicited lymphopenia resulting from a reversible redistribution of lymphocytes from circulation to secondary lymphoid tissues by unknown mechanisms. in a rodent model of multiple sclerosis, the phosphorylated fty720 compound was a potent agonist at four s s1p receptors. phosphorylation of fty720 acted through sphingosine 1-phosphate signaling pathways to modulate chemotactic responses and lymphocyte trafficking [1]. fty720 was phosphorylated in vivo. in mice, treatment with fty720 inhibited tissue sphingosine-1-phosphate lyase activity, whereas lyase gene and protein expression were not significantly affected [3].
references
[1] brinkmann v, davis m d, heise c e, et al. the immune modulator fty720 targets sphingosine 1-phosphate receptors[j]. journal of biological chemistry, 2002, 277(24): 21453-21457.[2] spiegel s, milstien s. sphingosine-1-phosphate: an enigmatic signalling lipid[j]. nature reviews molecular cell biology, 2003, 4(5): 397-407.[3] bandhuvula p, tam y y, oskouian b, et al. the immune modulator fty720 inhibits sphingosine-1-phosphate lyase activity[j]. journal of biological chemistry, 2005, 280(40): 33697-33700.
Check Digit Verification of cas no
The CAS Registry Mumber 402615-91-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,0,2,6,1 and 5 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 402615-91:
(8*4)+(7*0)+(6*2)+(5*6)+(4*1)+(3*5)+(2*9)+(1*1)=112
112 % 10 = 2
So 402615-91-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H34NO5P/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-25-26(22,23)24/h9-12,21H,2-8,13-16,20H2,1H3,(H2,22,23,24)
402615-91-2Relevant academic research and scientific papers
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
Albert, Rainer,Hinterding, Klaus,Brinkmann, Volker,Guerini, Danilo,Müller-Hartwieg, Constanze,Knecht, Helmut,Simeon, Corinne,Streiff, Markus,Wagner, Trixie,Weizenbach, Karl,Zécri, Frédéric,Zollinger, Markus,Cooke, Nigel,Francotte, Eric
, p. 5373 - 5377 (2007/10/03)
In vivo phosphorylation of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.
AMINOPROPANOL DERIVATIVES
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Page/Page column 11-12, (2008/06/13)
Compounds of formula (I): wherein R1, R2, n and m are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.
Phosphate derivatives as immunoregulatory agents
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, (2008/06/13)
Immunoregulatory compounds are disclosed of the formula: and as well as the pharmaceutically acceptable salts and hydrates thereof, are disclosed. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.
