Literature DB >> 25479771

Identification of potent inhibitors of the chicken soluble epoxide hydrolase.

Diyala S Shihadih1, Todd R Harris1, Jun Yang1, Oleg Merzlikin1, Kin Sing S Lee1, Bruce D Hammock1, Christophe Morisseau2.   

Abstract

In vertebrates, soluble epoxide hydrolase (sEH) hydrolyzes natural epoxy-fatty acids (EpFAs), which are chemical mediators modulating inflammation, pain, and angiogenesis. Chick embryos are used to study angiogenesis, particularly its role in cardiovascular biology and pathology. To find potent and bio-stable inhibitors of the chicken sEH (chxEH) a library of human sEH inhibitors was screened. Derivatives of 1(adamantan-1-yl)-3-(trans-4-phenoxycyclohexyl) urea were found to be very potent tight binding inhibitors (KI <150pM) of chxEH while being relatively stable in chicken liver microsomes, suggesting their usefulness to study the role of EpFAs in chickens.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Angiogenesis; Di-substituted ureas; Epoxy-eicosatrienoic acids; High throughput screening; Liver microsomes

Mesh：

Substances：

Year:  2014        PMID： 25479771      PMCID： PMC4277729          DOI： 10.1016/j.bmcl.2014.11.053

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


  25 in total

1.  Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.

Authors:  Vladimir Burmistrov; Christophe Morisseau; Kin Sing Stephen Lee; Diyala S Shihadih; Todd R Harris; Gennady M Butov; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2014-03-20       Impact factor: 2.823

2.  Substituted phenyl groups improve the pharmacokinetic profile and anti-inflammatory effect of urea-based soluble epoxide hydrolase inhibitors in murine models.

Authors:  Jun-Yan Liu; Yan-Ping Lin; Hong Qiu; Christophe Morisseau; Tristan E Rose; Sung Hee Hwang; Nipavan Chiamvimonvat; Bruce D Hammock
Journal:  Eur J Pharm Sci       Date:  2013-01-03       Impact factor: 4.384

3.  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

4.  Chick chorioallantoic membrane as an in vivo model to study vasoreactivity: characterization of development-dependent hyperemia induced by epoxyeicosatrienoic acids (EETs).

Authors:  Laurel K Dunn; Stephanie K Gruenloh; Bruce E Dunn; D Sudarshan Reddy; John R Falck; Elizabeth R Jacobs; Meetha Medhora
Journal:  Anat Rec A Discov Mol Cell Evol Biol       Date:  2005-08

5.  [Arachidonic acid epoxygenases and their metabolites promote angiogenesis].

Authors:  Yan Wang; Jia-ning Wang; Zhen-jun Liu; Xin Wei; Xiao Xiao; Dao-wen Wang
Journal:  Zhonghua Xin Xue Guan Bing Za Zhi       Date:  2005-12

Review 6.  Epoxides and soluble epoxide hydrolase in cardiovascular physiology.

Authors:  John D Imig
Journal:  Physiol Rev       Date:  2012-01       Impact factor: 37.312

7.  Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids.

Authors:  Christophe Morisseau; Bora Inceoglu; Kara Schmelzer; Hsing-Ju Tsai; Steven L Jinks; Christine M Hegedus; Bruce D Hammock
Journal:  J Lipid Res       Date:  2010-07-27       Impact factor: 5.922

Review 8.  Arachidonic acid cytochrome P450 epoxygenase pathway.

Authors:  Arthur A Spector
Journal:  J Lipid Res       Date:  2008-10-23       Impact factor: 5.922

9.  Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis.

Authors:  Guodong Zhang; Dipak Panigrahy; Lisa M Mahakian; Jun Yang; Jun-Yan Liu; Kin Sing Stephen Lee; Hiromi I Wettersten; Arzu Ulu; Xiaowen Hu; Sarah Tam; Sung Hee Hwang; Elizabeth S Ingham; Mark W Kieran; Robert H Weiss; Katherine W Ferrara; Bruce D Hammock
Journal:  Proc Natl Acad Sci U S A       Date:  2013-04-03       Impact factor: 11.205

Review 10.  Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer.

Authors:  Guodong Zhang; Sean Kodani; Bruce D Hammock
Journal:  Prog Lipid Res       Date:  2013-12-15       Impact factor: 16.195
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  3 in total

1.  Effects of adamantane alterations on soluble epoxide hydrolase inhibition potency, physical properties and metabolic stability.

Authors:  Vladimir Burmistrov; Christophe Morisseau; Todd R Harris; Gennady Butov; Bruce D Hammock
Journal:  Bioorg Chem       Date:  2017-12-30       Impact factor: 5.275

2.  1,3-Disubstituted and 1,3,3-trisubstituted adamantyl-ureas with isoxazole as soluble epoxide hydrolase inhibitors.

Authors:  Vladimir Burmistrov; Christophe Morisseau; Dmitry Danilov; Todd R Harris; Igor Dalinger; Irina Vatsadze; Tatiana Shkineva; Gennady M Butov; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2015-10-23       Impact factor: 2.823

3.  Selection of Potent Inhibitors of Soluble Epoxide Hydrolase for Usage in Veterinary Medicine.

Authors:  Diyala S Shihadih; Todd R Harris; Sean D Kodani; Sung-Hee Hwang; Kin Sing Stephen Lee; Vengai Mavangira; Briana Hamamoto; Alonso Guedes; Bruce D Hammock; Christophe Morisseau
Journal:  Front Vet Sci       Date:  2020-08-26
  3 in total

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