Literature DB >> 22079754

Design, synthesis and evaluation of non-urea inhibitors of soluble epoxide hydrolase.

Stevan Pecic1, Shi-Xian Deng, Christophe Morisseau, Bruce D Hammock, Donald W Landry.   

Abstract

Inhibition of soluble epoxide hydrolase (sEH) has been proposed as a new pharmaceutical approach for treating hypertension and vascular inflammation. The most potent sEH inhibitors reported in literature to date are urea derivatives. However, these compounds have limited pharmacokinetic profiles. We investigated non-urea amide derivatives as sEH inhibitors and identified a potent human sEH inhibitor 14-34 having potency comparable to urea-based inhibitors. Published by Elsevier Ltd.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 22079754      PMCID: PMC3337727          DOI: 10.1016/j.bmcl.2011.10.074

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


  26 in total

1.  Human soluble epoxide hydrolase: structural basis of inhibition by 4-(3-cyclohexylureido)-carboxylic acids.

Authors:  German A Gomez; Christophe Morisseau; Bruce D Hammock; David W Christianson
Journal:  Protein Sci       Date:  2005-12-01       Impact factor: 6.725

2.  Fluorescent substrates for soluble epoxide hydrolase and application to inhibition studies.

Authors:  Paul D Jones; Nicola M Wolf; Christophe Morisseau; Paul Whetstone; Bertold Hock; Bruce D Hammock
Journal:  Anal Biochem       Date:  2005-08-01       Impact factor: 3.365

3.  Synthesis and SAR of conformationally restricted inhibitors of soluble epoxide hydrolase.

Authors:  Paul D Jones; Hsing-Ju Tsai; Zung N Do; Christophe Morisseau; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2006-07-25       Impact factor: 2.823

4.  Binding of alkylurea inhibitors to epoxide hydrolase implicates active site tyrosines in substrate activation.

Authors:  M A Argiriadi; C Morisseau; M H Goodrow; D L Dowdy; B D Hammock; D W Christianson
Journal:  J Biol Chem       Date:  2000-05-19       Impact factor: 5.157

5.  Structural refinement of inhibitors of urea-based soluble epoxide hydrolases.

Authors:  Christophe Morisseau; Marvin H Goodrow; John W Newman; Craig E Wheelock; Deanna L Dowdy; Bruce D Hammock
Journal:  Biochem Pharmacol       Date:  2002-05-01       Impact factor: 5.858

6.  Design, synthesis, and biological activity of 1,3-disubstituted ureas as potent inhibitors of the soluble epoxide hydrolase of increased water solubility.

Authors:  In-Hae Kim; Christophe Morisseau; Takaho Watanabe; Bruce D Hammock
Journal:  J Med Chem       Date:  2004-04-08       Impact factor: 7.446

7.  Discovery of a highly potent, selective, and bioavailable soluble epoxide hydrolase inhibitor with excellent ex vivo target engagement.

Authors:  Hong C Shen; Fa-Xiang Ding; Siyi Wang; Qiaolin Deng; Xiaoping Zhang; Yuli Chen; Gaochao Zhou; Suoyu Xu; Hsuan-Shen Chen; Xinchun Tong; Vincent Tong; Kaushik Mitra; Sanjeev Kumar; Christine Tsai; Andra S Stevenson; Lee-Yuh Pai; Magdalena Alonso-Galicia; Xiaoli Chen; Stephen M Soisson; Sophie Roy; Bei Zhang; James R Tata; Joel P Berger; Steven L Colletti
Journal:  J Med Chem       Date:  2009-08-27       Impact factor: 7.446

8.  Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors.

Authors:  W B Campbell; D Gebremedhin; P F Pratt; D R Harder
Journal:  Circ Res       Date:  1996-03       Impact factor: 17.367

9.  Epoxyeicosatrienoic acids function as selective, endogenous antagonists of native thromboxane receptors: identification of a novel mechanism of vasodilation.

Authors:  David J Behm; Andrea Ogbonna; Charlene Wu; Cynthia L Burns-Kurtis; Stephen A Douglas
Journal:  J Pharmacol Exp Ther       Date:  2008-10-03       Impact factor: 4.030

10.  Discovery of potent non-urea inhibitors of soluble epoxide hydrolase.

Authors:  Yuli Xie; Yidong Liu; Gangli Gong; Deborah H Smith; Fang Yan; Alison Rinderspacher; Yan Feng; Zhengxiang Zhu; Xiangpo Li; Shi-Xian Deng; Lars Branden; Dusica Vidović; Caty Chung; Stephan Schürer; Christophe Morisseau; Bruce D Hammock; Donald W Landry
Journal:  Bioorg Med Chem Lett       Date:  2008-09-20       Impact factor: 2.823

View more
  9 in total

1.  Investigation of the binding mode of 1, 3, 4-oxadiazole derivatives as amide-based inhibitors for soluble epoxide hydrolase (sEH) by molecular docking and MM-GBSA.

Authors:  Leila Karami; Ali Akbar Saboury; Elham Rezaee; Sayyed Abbas Tabatabai
Journal:  Eur Biophys J       Date:  2016-12-07       Impact factor: 1.733

2.  Synthesis and structure-activity relationship of piperidine-derived non-urea soluble epoxide hydrolase inhibitors.

Authors:  Stevan Pecic; Svetlana Pakhomova; Marcia E Newcomer; Christophe Morisseau; Bruce D Hammock; Zhengxiang Zhu; Alison Rinderspacher; Shi-Xian Deng
Journal:  Bioorg Med Chem Lett       Date:  2012-12-01       Impact factor: 2.823

3.  Novel piperidine-derived amide sEH inhibitors as mediators of lipid metabolism with improved stability.

Authors:  Stevan Pecic; Amir A Zeki; Xiaoming Xu; Gina Y Jin; Shuwei Zhang; Sean Kodani; Marlin Halim; Christophe Morisseau; Bruce D Hammock; Shi-Xian Deng
Journal:  Prostaglandins Other Lipid Mediat       Date:  2018-03-20       Impact factor: 3.072

4.  Further exploration of the structure-activity relationship of dual soluble epoxide hydrolase/fatty acid amide hydrolase inhibitors.

Authors:  Stephanie Wilt; Sean Kodani; Leah Valencia; Paula K Hudson; Stephanie Sanchez; Taylor Quintana; Christophe Morisseau; Bruce D Hammock; Ram Kandasamy; Stevan Pecic
Journal:  Bioorg Med Chem       Date:  2021-11-11       Impact factor: 3.641

5.  Repositioning of Quinazolinedione-Based Compounds on Soluble Epoxide Hydrolase (sEH) through 3D Structure-Based Pharmacophore Model-Driven Investigation.

Authors:  Erica Gazzillo; Stefania Terracciano; Dafne Ruggiero; Marianna Potenza; Maria Giovanna Chini; Gianluigi Lauro; Katrin Fischer; Robert Klaus Hofstetter; Assunta Giordano; Oliver Werz; Ines Bruno; Giuseppe Bifulco
Journal:  Molecules       Date:  2022-06-16       Impact factor: 4.927

6.  N-Benzyl-linoleamide, a Constituent of Lepidium meyenii (Maca), Is an Orally Bioavailable Soluble Epoxide Hydrolase Inhibitor That Alleviates Inflammatory Pain.

Authors:  Nalin Singh; Bogdan Barnych; Christophe Morisseau; Karen M Wagner; Debin Wan; Ashley Takeshita; Hoang Pham; Ting Xu; Abhaya Dandekar; Jun-Yan Liu; Bruce D Hammock
Journal:  J Nat Prod       Date:  2020-12-15       Impact factor: 4.050

Review 7.  Small Molecule Soluble Epoxide Hydrolase Inhibitors in Multitarget and Combination Therapies for Inflammation and Cancer.

Authors:  Amarjyoti Das Mahapatra; Rinku Choubey; Bhaskar Datta
Journal:  Molecules       Date:  2020-11-24       Impact factor: 4.411

Review 8.  Discovery of Soluble Epoxide Hydrolase Inhibitors from Chemical Synthesis and Natural Products.

Authors:  Cheng-Peng Sun; Xin-Yue Zhang; Christophe Morisseau; Sung Hee Hwang; Zhan-Jun Zhang; Bruce D Hammock; Xiao-Chi Ma
Journal:  J Med Chem       Date:  2020-12-28       Impact factor: 7.446

9.  Discovery of Novel Soluble Epoxide Hydrolase Inhibitors as Potent Vasodilators.

Authors:  Neetika Tripathi; Sarvesh Paliwal; Swapnil Sharma; Kanika Verma; Ritika Gururani; Akanksha Tiwari; Amrita Verma; Monika Chauhan; Aarti Singh; Dipak Kumar; Aditya Pant
Journal:  Sci Rep       Date:  2018-10-02       Impact factor: 4.379

  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.