Literature DB >> 24900287

Discovery of a Potent, S1P3-Sparing Benzothiazole Agonist of Sphingosine-1-Phosphate Receptor 1 (S1P1).

Brian A Lanman1, Victor J Cee1, Srinivasa R Cheruku2, Mike Frohn1, Jennifer Golden1, Jian Lin2, Mercedes Lobera2, Yael Marantz2, Kristine M Muller1, Susana C Neira1, Alexander J Pickrell1, Dalia Rivenzon-Segal2, Nili Schutz2, Anurag Sharadendu2, Xiang Yu2, Zhaoda Zhang2, Janet Buys1, Mike Fiorino1, Anu Gore1, Michelle Horner1, Andrea Itano1, Michele McElvain1, Scot Middleton1, Michael Schrag1, Hugo M Vargas1, Han Xu1, Yang Xu1, Xuxia Zhang1, Jerry Siu1, Roland W Bürli1.   

Abstract

Optimization of a benzofuranyl S1P1 agonist lead compound (3) led to the discovery of 1-(3-fluoro-4-(5-(2-fluorobenzyl)benzo[d]thiazol-2-yl)benzyl)azetidine-3-carboxylic acid (14), a potent S1P1 agonist with minimal activity at S1P3. Dosed orally at 0.3 mg/kg, 14 significantly reduced blood lymphocyte counts 24 h postdose and attenuated a delayed type hypersensitivity (DTH) response to antigen challenge.

Entities:  

Keywords:  S1P1; Sphingosine-1-phosphate receptor; agonist; inflammation; lymphocyte

Year:  2010        PMID： 24900287      PMCID： PMC4018108          DOI： 10.1021/ml100228m

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  27 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.  PREDICT modeling and in-silico screening for G-protein coupled receptors.

Authors:  Sharon Shacham; Yael Marantz; Shay Bar-Haim; Ori Kalid; Dora Warshaviak; Noa Avisar; Boaz Inbal; Alexander Heifetz; Merav Fichman; Maya Topf; Zvi Naor; Silvia Noiman; Oren M Becker
Journal:  Proteins       Date:  2004-10-01

Review 3.  Chemokines, sphingosine-1-phosphate, and cell migration in secondary lymphoid organs.

Authors:  Jason G Cyster
Journal:  Annu Rev Immunol       Date:  2005       Impact factor: 28.527

Review 4.  Sphingosine 1-phosphate and its receptors: an autocrine and paracrine network.

Authors:  Hugh Rosen; Edward J Goetzl
Journal:  Nat Rev Immunol       Date:  2005-07       Impact factor: 53.106

5.  FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. I. FTY720 selectively decreases the number of circulating mature lymphocytes by acceleration of lymphocyte homing.

Authors:  K Chiba; Y Yanagawa; Y Masubuchi; H Kataoka; T Kawaguchi; M Ohtsuki; Y Hoshino
Journal:  J Immunol       Date:  1998-05-15       Impact factor: 5.422

6.  A placebo-controlled trial of oral fingolimod in relapsing multiple sclerosis.

Authors:  Ludwig Kappos; Ernst-Wilhelm Radue; Paul O'Connor; Chris Polman; Reinhard Hohlfeld; Peter Calabresi; Krzysztof Selmaj; Catherine Agoropoulou; Malgorzata Leyk; Lixin Zhang-Auberson; Pascale Burtin
Journal:  N Engl J Med       Date:  2010-01-20       Impact factor: 91.245

7.  Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.

Authors:  M Germana Sanna; Jiayu Liao; Euijung Jo; Christopher Alfonso; Min-Young Ahn; Melissa S Peterson; Bill Webb; Sophie Lefebvre; Jerold Chun; Nathanael Gray; Hugh Rosen
Journal:  J Biol Chem       Date:  2004-01-19       Impact factor: 5.157

Review 8.  Metabolism and biological functions of two phosphorylated sphingolipids, sphingosine 1-phosphate and ceramide 1-phosphate.

Authors:  Akio Kihara; Susumu Mitsutake; Yukiko Mizutani; Yasuyuki Igarashi
Journal:  Prog Lipid Res       Date:  2007-03-14       Impact factor: 16.195

9.  Requirement of secondary lymphoid tissues for the induction of primary and secondary T cell responses against Listeria monocytogenes.

Authors:  Mischo Kursar; Nathalie Jänner; Klaus Pfeffer; Volker Brinkmann; Stefan H E Kaufmann; Hans-Willi Mittrücker
Journal:  Eur J Immunol       Date:  2008-01       Impact factor: 5.532

10.  FTY720 story. Its discovery and the following accelerated development of sphingosine 1-phosphate receptor agonists as immunomodulators based on reverse pharmacology.

Authors:  Kunitomo Adachi; Kenji Chiba
Journal:  Perspect Medicin Chem       Date:  2007-09-06
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  2 in total

1.  Discovery of a Selective S1P1 Receptor Agonist Efficacious at Low Oral Dose and Devoid of Effects on Heart Rate.

Authors:  Emmanuel H Demont; Benjamin I Andrews; Rino A Bit; Colin A Campbell; Jason W B Cooke; Nigel Deeks; Sapna Desai; Simon J Dowell; Pam Gaskin; James R J Gray; Andrea Haynes; Duncan S Holmes; Umesh Kumar; Mary A Morse; Greg J Osborne; Terry Panchal; Bela Patel; Alcide Perboni; Simon Taylor; Robert Watson; Jason Witherington; Robert Willis
Journal:  ACS Med Chem Lett       Date:  2011-03-24       Impact factor: 4.345

2.  Discovery of AMG 369, a Thiazolo[5,4-b]pyridine Agonist of S1P1 and S1P5.

Authors:  Victor J Cee; Mike Frohn; Brian A Lanman; Jennifer Golden; Kristine Muller; Susana Neira; Alex Pickrell; Heather Arnett; Janet Buys; Anu Gore; Mike Fiorino; Michelle Horner; Andrea Itano; Matt R Lee; Michele McElvain; Scot Middleton; Michael Schrag; Dalia Rivenzon-Segal; Hugo M Vargas; Han Xu; Yang Xu; Xuxia Zhang; Jerry Siu; Min Wong; Roland W Bürli
Journal:  ACS Med Chem Lett       Date:  2010-12-29       Impact factor: 4.345
  2 in total

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