Literature DB >> 19296586

Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720.

Xuequan Lu1, Chaode Sun, William J Valentine, E Shuyu, Jianxiong Liu, Gabor Tigyi, Robert Bittman.   

Abstract

The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)-vinylphosphonate (S)-5, but not its R enantiomer, elicited a potent antiapoptotic effect in intestinal epithelial cells, suggesting that it exerts its action via the enantioselective activation of a receptor. (S)-5 failed to activate the sphingosine 1-phosphate type 1 (S1P(1)) receptor.

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Year:  2009        PMID： 19296586      PMCID： PMC2747615          DOI： 10.1021/jo900023u

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  20 in total

1.  Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists.

Authors:  Suzanne Mandala; Richard Hajdu; James Bergstrom; Elizabeth Quackenbush; Jenny Xie; James Milligan; Rosemary Thornton; Gan-Ju Shei; Deborah Card; CarolAnn Keohane; Mark Rosenbach; Jeffrey Hale; Christopher L Lynch; Kathleen Rupprecht; William Parsons; Hugh Rosen
Journal:  Science       Date:  2002-03-28       Impact factor: 47.728

2.  Potent S1P receptor agonists replicate the pharmacologic actions of the novel immune modulator FTY720.

Authors:  Jeffrey J Hale; William Neway; Sander G Mills; Richard Hajdu; Carol Ann Keohane; Mark Rosenbach; James Milligan; Gan-Ju Shei; Gary Chrebet; James Bergstrom; Deborah Card; Gloria C Koo; Sam L Koprak; Jesse J Jackson; Hugh Rosen; Suzanne Mandala
Journal:  Bioorg Med Chem Lett       Date:  2004-06-21       Impact factor: 2.823

3.  Synthesis, stereochemical determination and biochemical characterization of the enantiomeric phosphate esters of the novel immunosuppressive agent FTY720.

Authors:  Jeffrey J Hale; Lin Yan; William E Neway; Richard Hajdu; James D Bergstrom; James A Milligan; Gan-Ju Shei; Gary L Chrebet; Rosemary A Thornton; Deborah Card; Mark Rosenbach; Suzanne Mandala
Journal:  Bioorg Med Chem       Date:  2004-09-15       Impact factor: 3.641

4.  Oral fingolimod (FTY720) for relapsing multiple sclerosis.

Authors:  Ludwig Kappos; Jack Antel; Giancarlo Comi; Xavier Montalban; Paul O'Connor; Chris H Polman; Tomas Haas; Alexander A Korn; Goeril Karlsson; Ernst W Radue
Journal:  N Engl J Med       Date:  2006-09-14       Impact factor: 91.245

5.  The immunomodulator FTY720 has a direct cytoprotective effect in oligodendrocyte progenitors.

Authors:  Rochelle P Coelho; Shawn G Payne; Robert Bittman; Sarah Spiegel; Carmen Sato-Bigbee
Journal:  J Pharmacol Exp Ther       Date:  2007-08-28       Impact factor: 4.030

Review 6.  Camptothecins: a SAR/QSAR study.

Authors:  Rajeshwar P Verma; Corwin Hansch
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

7.  Mapping pathways downstream of sphingosine 1-phosphate subtype 1 by differential chemical perturbation and proteomics.

Authors:  Pedro J Gonzalez-Cabrera; Timothy Hla; Hugh Rosen
Journal:  J Biol Chem       Date:  2007-01-10       Impact factor: 5.157

Review 8.  FTY720, an immunomodulatory sphingolipid mimetic: translation of a novel mechanism into clinical benefit in multiple sclerosis.

Authors:  Thomas Baumruker; Andreas Billich; Volker Brinkmann
Journal:  Expert Opin Investig Drugs       Date:  2007-03       Impact factor: 6.206

9.  Novel role of sphingosine kinase 1 as a mediator of neurotrophin-3 action in oligodendrocyte progenitors.

Authors:  Harsimran S Saini; Rochelle P Coelho; Sravan K Goparaju; Puneet S Jolly; Michael Maceyka; Sarah Spiegel; Carmen Sato-Bigbee
Journal:  J Neurochem       Date:  2005-12       Impact factor: 5.372

10.  Synthesis of the key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate, of the immunomodulatory agent FTY720 (fingolimod).

Authors:  Norimasa Matsumoto; Ryoji Hirose; Shigeo Sasaki; Tetsuro Fujita
Journal:  Chem Pharm Bull (Tokyo)       Date:  2008-04       Impact factor: 1.645
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  26 in total

1.  Pulmonary endothelial cell barrier enhancement by novel FTY720 analogs: methoxy-FTY720, fluoro-FTY720, and β-glucuronide-FTY720.

Authors:  Sara M Camp; Eddie T Chiang; Chaode Sun; Peter V Usatyuk; Robert Bittman; Viswanathan Natarajan; Joe G N Garcia; Steven M Dudek
Journal:  Chem Phys Lipids       Date:  2015-08-10       Impact factor: 3.329

2.  (R)-FTY720 methyl ether is a specific sphingosine kinase 2 inhibitor: Effect on sphingosine kinase 2 expression in HEK 293 cells and actin rearrangement and survival of MCF-7 breast cancer cells.

Authors:  Keng Gat Lim; Chaode Sun; Robert Bittman; Nigel J Pyne; Susan Pyne
Journal:  Cell Signal       Date:  2011-05-18       Impact factor: 4.315

3.  Endothelial disruptive proinflammatory effects of nicotine and e-cigarette vapor exposures.

Authors:  Kelly S Schweitzer; Steven X Chen; Sarah Law; Mary Van Demark; Christophe Poirier; Matthew J Justice; Walter C Hubbard; Elena S Kim; Xianyin Lai; Mu Wang; William D Kranz; Clinton J Carroll; Bruce D Ray; Robert Bittman; John Goodpaster; Irina Petrache
Journal:  Am J Physiol Lung Cell Mol Physiol       Date:  2015-05-15       Impact factor: 5.464

4.  FTY720 (s)-phosphonate preserves sphingosine 1-phosphate receptor 1 expression and exhibits superior barrier protection to FTY720 in acute lung injury.

Authors:  Lichun Wang; Saad Sammani; Liliana Moreno-Vinasco; Eleftheria Letsiou; Ting Wang; Sara M Camp; Robert Bittman; Joe G N Garcia; Steven M Dudek
Journal:  Crit Care Med       Date:  2014-03       Impact factor: 7.598

5.  Inhibition of serine palmitoyltransferase delays the onset of radiation-induced pulmonary fibrosis through the negative regulation of sphingosine kinase-1 expression.

Authors:  Irina Gorshkova; Tong Zhou; Biji Mathew; Jeffrey R Jacobson; Daisuke Takekoshi; Palash Bhattacharya; Brett Smith; Bulent Aydogan; Ralph R Weichselbaum; Viswanathan Natarajan; Joe G N Garcia; Evgeny V Berdyshev
Journal:  J Lipid Res       Date:  2012-05-21       Impact factor: 5.922

6.  Synthesis of (S)-FTY720 vinylphosphonate analogues and evaluation of their potential as sphingosine kinase 1 inhibitors and activators.

Authors:  Zheng Liu; Neil MacRitchie; Susan Pyne; Nigel J Pyne; Robert Bittman
Journal:  Bioorg Med Chem       Date:  2013-03-07       Impact factor: 3.641

7.  FTY720 (Gilenya) phosphate selectivity of sphingosine 1-phosphate receptor subtype 1 (S1P1) G protein-coupled receptor requires motifs in intracellular loop 1 and transmembrane domain 2.

Authors:  William J Valentine; Virginia I Godwin; Daniel A Osborne; Jianxiong Liu; Yuko Fujiwara; James Van Brocklyn; Robert Bittman; Abby L Parrill; Gabor Tigyi
Journal:  J Biol Chem       Date:  2011-06-30       Impact factor: 5.157

8.  FTY720 and (S)-FTY720 vinylphosphonate inhibit sphingosine kinase 1 and promote its proteasomal degradation in human pulmonary artery smooth muscle, breast cancer and androgen-independent prostate cancer cells.

Authors:  Francesca Tonelli; Keng Gat Lim; Carolyn Loveridge; Jaclyn Long; Stuart M Pitson; Gabor Tigyi; Robert Bittman; Susan Pyne; Nigel J Pyne
Journal:  Cell Signal       Date:  2010-06-04       Impact factor: 4.315

Review 9.  Sphingosine-1-phosphate, FTY720, and sphingosine-1-phosphate receptors in the pathobiology of acute lung injury.

Authors:  Viswanathan Natarajan; Steven M Dudek; Jeffrey R Jacobson; Liliana Moreno-Vinasco; Long Shuang Huang; Taimur Abassi; Biji Mathew; Yutong Zhao; Lichun Wang; Robert Bittman; Ralph Weichselbaum; Evgeny Berdyshev; Joe G N Garcia
Journal:  Am J Respir Cell Mol Biol       Date:  2013-07       Impact factor: 6.914

10.  Ceramide synthesis is modulated by the sphingosine analog FTY720 via a mixture of uncompetitive and noncompetitive inhibition in an Acyl-CoA chain length-dependent manner.

Authors:  Sujoy Lahiri; Hyejung Park; Elad L Laviad; Xuequan Lu; Robert Bittman; Anthony H Futerman
Journal:  J Biol Chem       Date:  2009-04-08       Impact factor: 5.157
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