Literature DB >> 20172724

Ethacrynic acid analogues lacking the alpha,beta-unsaturated carbonyl unit--potential anti-metastatic drugs.

Romy F J Janser1, Ranjith K Meka, Zack E Bryant, Enoch A Adogla, Elizabeth K Vogel, Jaimie L Wharton, Cynthia M Tilley, Catherine N Kaminski, Seth L Ferrey, Severine Van Slambrouck, Wim F A Steelant, Ingo Janser.   

Abstract

A series of ethacrynic acid analogues, lacking the alpha,beta-unsaturated carbonyl unit, was synthesized and subsequently evaluated for their ability to inhibit the migration of human breast cancer cells, MCF-7/AZ. Several of the analogues were already active in the low micromolar range, whereas ethacrynic acid itself shows no potential to inhibit the migration of these cancer cells. Preliminary studies show that the presence of one or more methoxy groups at the phenyl ring of ethacrynic acid is important in order for the ethacrynic acid analogues to demonstrate an inhibitory effect on the migration. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID: 20172724      PMCID: PMC2839078          DOI: 10.1016/j.bmcl.2010.01.144

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  11 in total

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Authors:  P R Twentyman; E Lambert; M Müller; J K Rees
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Review 3.  Advance in antitumor agents targeting glutathione-S-transferase.

Authors:  Guisen Zhao; Xiaobing Wang
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4.  Synthesis and structure-activity relationship of ethacrynic acid analogues on glutathione-s-transferase P1-1 activity inhibition.

Authors:  Guisen Zhao; Tao Yu; Rui Wang; Xiaobing Wang; Yongkui Jing
Journal:  Bioorg Med Chem       Date:  2005-06-02       Impact factor: 3.641

5.  Inhibition of glutathione S-transferase activity in human melanoma cells by alpha,beta-unsaturated carbonyl derivatives. Effects of acrolein, cinnamaldehyde, citral, crotonaldehyde, curcumin, ethacrynic acid, and trans-2-hexenal.

Authors:  M L Iersel; J P Ploemen; I Struik; C van Amersfoort; A E Keyzer; J G Schefferlie; P J van Bladeren
Journal:  Chem Biol Interact       Date:  1996-10-21       Impact factor: 5.192

6.  Characterization of cell death induced by ethacrynic acid in a human colon cancer cell line DLD-1 and suppression by N-acetyl-L-cysteine.

Authors:  Shu Aizawa; Keizou Ookawa; Toshihiro Kudo; Junpei Asano; Makoto Hayakari; Shigeki Tsuchida
Journal:  Cancer Sci       Date:  2003-10       Impact factor: 6.716

7.  The synthesis of alpha,beta-unsaturated carbonyl derivatives with the ability to inhibit both glutathione S-transferase P1-1 activity and the proliferation of leukemia cells.

Authors:  Guisen Zhao; Chuan Liu; Rui Wang; Dandan Song; Xiaobing Wang; Hongxiang Lou; Yongkui Jing
Journal:  Bioorg Med Chem       Date:  2007-01-24       Impact factor: 3.641

8.  The pathogenesis of cancer metastasis: the 'seed and soil' hypothesis revisited.

Authors:  Isaiah J Fidler
Journal:  Nat Rev Cancer       Date:  2003-06       Impact factor: 60.716

9.  Amide derivatives of ethacrynic acid: synthesis and evaluation as antagonists of Wnt/beta-catenin signaling and CLL cell survival.

Authors:  Guangyi Jin; Desheng Lu; Shiyin Yao; Christina C N Wu; Jerry X Liu; Dennis A Carson; Howard B Cottam
Journal:  Bioorg Med Chem Lett       Date:  2008-12-24       Impact factor: 2.823

10.  AsialoGM1 and integrin alpha2beta1 mediate prostate cancer progression.

Authors:  Severine Van Slambrouck; John Hilkens; Marco Bisoffi; Wim F A Steelant
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  4 in total

1.  Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation.

Authors:  Enoch A Adogla; Romy F J Janser; Samuel S Fairbanks; Caitlyn M Vortolomei; Ranjith K Meka; Ingo Janser
Journal:  Tetrahedron Lett       Date:  2012-01-04       Impact factor: 2.415

2.  Inhibitory effects of ethacrynic acid analogues lacking the α,β-unsaturated carbonyl unit and para-acylated phenols on human cancer cells.

Authors:  Zack E Bryant; Romy F J Janser; Medina Jabarkhail; Melissa S Candelaria-Lyons; Brittni B Romero; Severine Van slambrouck; Wim F A Steelant; Ingo Janser
Journal:  Bioorg Med Chem Lett       Date:  2010-12-19       Impact factor: 2.823

3.  Ethacrynic acid improves the antitumor effects of irreversible epidermal growth factor receptor tyrosine kinase inhibitors in breast cancer.

Authors:  Bing Liu; XinPing Huang; YunLong Hu; TingTing Chen; BoYa Peng; NingNing Gao; ZhenChao Jin; TieLiu Jia; Na Zhang; ZhuLin Wang; GuangYi Jin
Journal:  Oncotarget       Date:  2016-09-06

Review 4.  A Review on the Pharmacological Activities and Phytochemicals of Alpinia officinarum (Galangal) Extracts Derived from Bioassay-Guided Fractionation and Isolation.

Authors:  Aida Maryam Basri; Hussein Taha; Norhayati Ahmad
Journal:  Pharmacogn Rev       Date:  2017 Jan-Jun
  4 in total

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