Literature DB >> 18082408

alpha- and beta-substituted phosphonate analogs of LPA as autotaxin inhibitors.

Peng Cui1, William F McCalmont, Jose L Tomsig, Kevin R Lynch, Timothy L Macdonald.   

Abstract

Autotaxin (ATX) is an attractive pharmacological target due to its lysophospholipase D activity which leads to the production of lysophosphatidic acid (LPA). Blockage of ATX produced LPA by small molecules could be a potential anticancer chemotherapy. In our previous study, we have identified the two beta-hydroxy phosphonate analogs of LPA (compounds f17 and f18) as ATX inhibitors. With this work, we investigated alpha- and beta-substituted phosphonate analogs of LPA and evaluated them for ATX inhibitory activity. The stereochemistry of beta-hydroxy phosphonates was also studied.

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Year:  2007        PMID： 18082408      PMCID： PMC2907913          DOI： 10.1016/j.bmc.2007.11.078

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  35 in total

1.  Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors.

Authors:  Peng Cui; Jose L Tomsig; William F McCalmont; Sangderk Lee; Christopher J Becker; Kevin R Lynch; Timothy L Macdonald
Journal:  Bioorg Med Chem Lett       Date:  2007-01-13       Impact factor: 2.823

Review 2.  Nucleotide pyrophosphatases/phosphodiesterases on the move.

Authors:  M Bollen; R Gijsbers; H Ceulemans; W Stalmans; C Stefan
Journal:  Crit Rev Biochem Mol Biol       Date:  2000       Impact factor: 8.250

3.  Autotaxin (NPP-2), a metastasis-enhancing motogen, is an angiogenic factor.

Authors:  S W Nam; T Clair; Y S Kim; A McMarlin; E Schiffmann; L A Liotta; M L Stracke
Journal:  Cancer Res       Date:  2001-09-15       Impact factor: 12.701

4.  Lysophosphatidic acid, a growth factor-like lipid, in the saliva.

Authors:  Takayuki Sugiura; Shinji Nakane; Seishi Kishimoto; Keizo Waku; Yasuko Yoshioka; Akira Tokumura
Journal:  J Lipid Res       Date:  2002-12       Impact factor: 5.922

5.  Identification of human plasma lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase.

Authors:  Akira Tokumura; Eiji Majima; Yuko Kariya; Kyoko Tominaga; Kentaro Kogure; Katsuhiko Yasuda; Kenji Fukuzawa
Journal:  J Biol Chem       Date:  2002-08-09       Impact factor: 5.157

6.  Lysophosphatidic acid protects and rescues intestinal epithelial cells from radiation- and chemotherapy-induced apoptosis.

Authors:  Wenlin Deng; Louisa Balazs; De-An Wang; Lester Van Middlesworth; Gabor Tigyi; Leonard R Johnson
Journal:  Gastroenterology       Date:  2002-07       Impact factor: 22.682

7.  Expression of autotaxin (NPP-2) is closely linked to invasiveness of breast cancer cells.

Authors:  So Young Yang; Jangsoon Lee; Chang Gyo Park; Seonghwan Kim; Sungyoul Hong; Hyun Cheol Chung; Seong Ki Min; Jeung Whan Han; Hyang Woo Lee; Hoi Young Lee
Journal:  Clin Exp Metastasis       Date:  2002       Impact factor: 5.150

Review 8.  Modulation of gastrointestinal wound repair and inflammation by phospholipids.

Authors:  Andreas Sturm; Axel U Dignass
Journal:  Biochim Biophys Acta       Date:  2002-05-23

Review 9.  Ecto-enzymes: physiology meets pathology.

Authors:  J W Goding
Journal:  J Leukoc Biol       Date:  2000-03       Impact factor: 4.962

10.  Autotaxin has lysophospholipase D activity leading to tumor cell growth and motility by lysophosphatidic acid production.

Authors:  Makiko Umezu-Goto; Yasuhiro Kishi; Akitsu Taira; Kotaro Hama; Naoshi Dohmae; Koji Takio; Takao Yamori; Gordon B Mills; Keizo Inoue; Junken Aoki; Hiroyuki Arai
Journal:  J Cell Biol       Date:  2002-07-15       Impact factor: 10.539
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  13 in total

1.  Boronic acid-based inhibitor of autotaxin reveals rapid turnover of LPA in the circulation.

Authors:  Harald M H G Albers; Anping Dong; Laurens A van Meeteren; David A Egan; Manjula Sunkara; Erica W van Tilburg; Karianne Schuurman; Olaf van Tellingen; Andrew J Morris; Susan S Smyth; Wouter H Moolenaar; Huib Ovaa
Journal:  Proc Natl Acad Sci U S A       Date:  2010-04-01       Impact factor: 11.205

2.  Developing novel organocatalyzed aldol reactions for the enantioselective synthesis of biologically active molecules.

Authors:  Mayur Bhanushali; Cong-Gui Zhao
Journal:  Synthesis (Stuttg)       Date:  2011-06       Impact factor: 3.157

3.  Crystallization and preliminary X-ray diffraction analysis of rat autotaxin.

Authors:  Jacqueline E Day; Troii Hall; Lyle E Pegg; Timothy E Benson; Jens Hausmann; Satwik Kamtekar
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2010-08-31

4.  Synthesis and structure-activity relationships of tyrosine-based inhibitors of autotaxin (ATX).

Authors:  James E East; Andrew J Kennedy; Jose L Tomsig; Alexandra R De Leon; Kevin R Lynch; Timothy L Macdonald
Journal:  Bioorg Med Chem Lett       Date:  2010-09-15       Impact factor: 2.823

5.  Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of α-hydroxyphosphonates induced by deoxyfluorinating reagents.

Authors:  Patrycja Kaczmarek; Magdalena Rapp; Henryk Koroniak
Journal:  RSC Adv       Date:  2018-07-06       Impact factor: 4.036

Review 6.  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 7.  ATX-LPA receptor axis in inflammation and cancer.

Authors:  Shuying Liu; Mandi Murph; Nattapon Panupinthu; Gordon B Mills
Journal:  Cell Cycle       Date:  2009-11-27       Impact factor: 4.534

8.  Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine.

Authors:  Mario Ordóñez; Selene Lagunas-Rivera; Emanuel Hernández-Núñez; Victoria Labastida-Galván
Journal:  Molecules       Date:  2010-03-04       Impact factor: 4.411

Review 9.  Chemical evolution of autotaxin inhibitors.

Authors:  Harald M H G Albers; Huib Ovaa
Journal:  Chem Rev       Date:  2012-02-15       Impact factor: 60.622

10.  New Zealand glowworm (Arachnocampa luminosa) bioluminescence is produced by a firefly-like luciferase but an entirely new luciferin.

Authors:  Oliver C Watkins; Miriam L Sharpe; Nigel B Perry; Kurt L Krause
Journal:  Sci Rep       Date:  2018-02-19       Impact factor: 4.379
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