Literature DB >> 18284246

Synthesis, pharmacology, and cell biology of sn-2-aminooxy analogues of lysophosphatidic acid.

Joanna Gajewiak1, Ryoko Tsukahara, Yuko Fujiwara, Gabor Tigyi, Glenn D Prestwich.   

Abstract

An efficient enantioselective synthesis of sn-2-aminooxy (AO) analogues of lysophosphatidic acid (LPA) that possess palmitoyl and oleoyl acyl chains is presented. Both sn-2-AO LPA analogues are agonists for the LPA1, LPA2, and LPA4 G-protein-coupled receptors, but antagonists for the LPA3 receptor and inhibitors of autotaxin (ATX). Moreover, both analogues stimulate migration of intestinal epithelial cells in a scratch wound assay.

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Year:  2008        PMID： 18284246      PMCID： PMC3510981          DOI： 10.1021/ol7030747

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  25 in total

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Journal:  Anticancer Res       Date:  2002 Mar-Apr       Impact factor: 2.480

Review 2.  Lysophosphatidic acid signaling: how a small lipid does big things.

Authors:  Celine Luquain; Vicki A Sciorra; Andrew J Morris
Journal:  Trends Biochem Sci       Date:  2003-07       Impact factor: 13.807

3.  Antimalarial activities of aminooxy compounds.

Authors:  B J Berger
Journal:  Antimicrob Agents Chemother       Date:  2000-09       Impact factor: 5.191

Review 4.  Lysophosphatidic acid production and action: validated targets in cancer?

Authors:  Makiko Umezu-Goto; Janos Tanyi; John Lahad; Shuying Liu; Shuangxing Yu; Ruth Lapushin; Yutaka Hasegawa; Yiling Lu; Rosanne Trost; Therese Bevers; Eric Jonasch; Ken Aldape; Jinsong Liu; Robyn D James; Colin G Ferguson; Yong Xu; Glenn D Prestwich; Gordon B Mills
Journal:  J Cell Biochem       Date:  2004-08-15       Impact factor: 4.429

5.  Enantioselective responses to a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity.

Authors:  Lian Qian; Yong Xu; Yutaka Hasegawa; Junken Aoki; Gordon B Mills; Glenn D Prestwich
Journal:  J Med Chem       Date:  2003-12-18       Impact factor: 7.446

6.  Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family.

Authors:  Kyoko Noguchi; Satoshi Ishii; Takao Shimizu
Journal:  J Biol Chem       Date:  2003-04-30       Impact factor: 5.157

Review 7.  The emerging role of lysophosphatidic acid in cancer.

Authors:  Gordon B Mills; Wouter H Moolenaar
Journal:  Nat Rev Cancer       Date:  2003-08       Impact factor: 60.716

8.  Synthesis of monofluorinated analogues of lysophosphatidic acid.

Authors:  Yong Xu; Lian Qian; Glenn D Prestwich
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354

9.  Lysophosphatidic acid and autotaxin stimulate cell motility of neoplastic and non-neoplastic cells through LPA1.

Authors:  Kotaro Hama; Junken Aoki; Masahiro Fukaya; Yasuhiro Kishi; Teruyuki Sakai; Rika Suzuki; Hideo Ohta; Takao Yamori; Masahiko Watanabe; Jerold Chun; Hiroyuki Arai
Journal:  J Biol Chem       Date:  2004-01-26       Impact factor: 5.157

10.  Synthesis of migration-resistant hydroxyethoxy analogues of lysophosphatidic acid.

Authors:  Lian Qian; Yong Xu; Hiroyuki Arai; Junken Aoki; Thomas M McIntyre; Glenn D Prestwich
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  5 in total

Review 1.  International Union of Basic and Clinical Pharmacology. LXXVIII. Lysophospholipid receptor nomenclature.

Authors:  Jerold Chun; Timothy Hla; Kevin R Lynch; Sarah Spiegel; Wouter H Moolenaar
Journal:  Pharmacol Rev       Date:  2010-12       Impact factor: 25.468

2.  Benzyl and naphthalene methylphosphonic acid inhibitors of autotaxin with anti-invasive and anti-metastatic activity.

Authors:  Renuka Gupte; Renukadevi Patil; Jianxiong Liu; Yaohong Wang; Sue C Lee; Yuko Fujiwara; James Fells; Alyssa L Bolen; Karin Emmons-Thompson; C Ryan Yates; Anjaih Siddam; Nattapon Panupinthu; Truc-Chi T Pham; Daniel L Baker; Abby L Parrill; Gordon B Mills; Gabor Tigyi; Duane D Miller
Journal:  ChemMedChem       Date:  2011-04-04       Impact factor: 3.466

Review 3.  Phosphatase-resistant analogues of lysophosphatidic acid: agonists promote healing, antagonists and autotaxin inhibitors treat cancer.

Authors:  Glenn D Prestwich; Joanna Gajewiak; Honglu Zhang; Xiaoyu Xu; Guanghui Yang; Monica Serban
Journal:  Biochim Biophys Acta       Date:  2008-04-08

Review 4.  Therapeutic potential of autotaxin/lysophospholipase d inhibitors.

Authors:  Lorenzo Federico; Zehra Pamuklar; Susan S Smyth; Andrew J Morris
Journal:  Curr Drug Targets       Date:  2008-08       Impact factor: 3.465

Review 5.  LPA receptor signaling: pharmacology, physiology, and pathophysiology.

Authors:  Yun C Yung; Nicole C Stoddard; Jerold Chun
Journal:  J Lipid Res       Date:  2014-03-18       Impact factor: 5.922
  5 in total

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