Literature DB >> 29298899

Epoxide hydrolase 1 (EPHX1) hydrolyzes epoxyeicosanoids and impairs cardiac recovery after ischemia.

Matthew L Edin1, Behin Gholipour Hamedani2, Artiom Gruzdev1, Joan P Graves1, Fred B Lih1, Samuel J Arbes1, Rohanit Singh1, Anette C Orjuela Leon2, J Alyce Bradbury1, Laura M DeGraff1, Samantha L Hoopes1, Michael Arand2, Darryl C Zeldin3.   

Abstract

Stimuli such as inflammation or hypoxia induce cytochrome P450 epoxygenase-mediated production of arachidonic acid-derived epoxyeicosatrienoic acids (EETs). EETs have cardioprotective, vasodilatory, angiogenic, anti-inflammatory, and analgesic effects, which are diminished by EET hydrolysis yielding biologically less active dihydroxyeicosatrienoic acids (DHETs). Previous in vitro assays have suggested that epoxide hydrolase 2 (EPHX2) is responsible for nearly all EET hydrolysis. EPHX1, which exhibits slow EET hydrolysis in vitro, is thought to contribute only marginally to EET hydrolysis. Using Ephx1-/-, Ephx2-/-, and Ephx1-/-Ephx2-/- mice, we show here that EPHX1 significantly contributes to EET hydrolysis in vivo Disruption of Ephx1 and/or Ephx2 genes did not induce compensatory changes in expression of other Ephx genes or CYP2 family epoxygenases. Plasma levels of 8,9-, 11,12-, and 14,15-DHET were reduced by 38, 44, and 67% in Ephx2-/- mice compared with wildtype (WT) mice, respectively; however, plasma from Ephx1-/-Ephx2-/- mice exhibited significantly greater reduction (100, 99, and 96%) of those respective DHETs. Kinetic assays and FRET experiments indicated that EPHX1 is a slow EET scavenger, but hydrolyzes EETs in a coupled reaction with cytochrome P450 to limit basal EET levels. Moreover, we also found that EPHX1 activities are biologically relevant, as Ephx1-/-Ephx2-/- hearts had significantly better postischemic functional recovery (71%) than both WT (31%) and Ephx2-/- (51%) hearts. These findings indicate that Ephx1-/-Ephx2-/- mice are a valuable model for assessing EET-mediated effects, uncover a new paradigm for EET metabolism, and suggest that dual EPHX1 and EPHX2 inhibition may represent a therapeutic approach to manage human pathologies such as myocardial infarction.

Entities:  

Keywords:  cardiac muscle; cardiovascular disease; cytochrome P450; eicosanoid biosynthesis; epoxyeicosatrienoic acid (EETs); ischemia; microsomal epoxide hydrolase; soluble epoxide hydrolase

Mesh:

Substances:

Year:  2018        PMID: 29298899      PMCID: PMC5836130          DOI: 10.1074/jbc.RA117.000298

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  50 in total

1.  Pharmacokinetics and pharmacodynamics of AR9281, an inhibitor of soluble epoxide hydrolase, in single- and multiple-dose studies in healthy human subjects.

Authors:  Dawn Chen; Randall Whitcomb; Euan MacIntyre; Vinh Tran; Zung N Do; James Sabry; Dinesh V Patel; Sampath K Anandan; Richard Gless; Heather K Webb
Journal:  J Clin Pharmacol       Date:  2011-03-21       Impact factor: 3.126

2.  The biological actions of 11,12-epoxyeicosatrienoic acid in endothelial cells are specific to the R/S-enantiomer and require the G(s) protein.

Authors:  Yindi Ding; Timo Frömel; Rüdiger Popp; John R Falck; Wolf-Hagen Schunck; Ingrid Fleming
Journal:  J Pharmacol Exp Ther       Date:  2014-04-24       Impact factor: 4.030

3.  Cytochromes P450 catalyze both steps of the major pathway of clopidogrel bioactivation, whereas paraoxonase catalyzes the formation of a minor thiol metabolite isomer.

Authors:  Patrick M Dansette; Julien Rosi; Gildas Bertho; Daniel Mansuy
Journal:  Chem Res Toxicol       Date:  2011-12-01       Impact factor: 3.739

4.  Human coronary endothelial cells convert 14,15-EET to a biologically active chain-shortened epoxide.

Authors:  Xiang Fang; Neal L Weintraub; Christine L Oltman; Lynn L Stoll; Terry L Kaduce; Shawn Harmon; Kevin C Dellsperger; Christophe Morisseau; Bruce D Hammock; Arthur A Spector
Journal:  Am J Physiol Heart Circ Physiol       Date:  2002-08-22       Impact factor: 4.733

Review 5.  Role of epoxyeicosatrienoic acids in protecting the myocardium following ischemia/reperfusion injury.

Authors:  John M Seubert; Darryl C Zeldin; Kasem Nithipatikom; Garrett J Gross
Journal:  Prostaglandins Other Lipid Mediat       Date:  2006-07-10       Impact factor: 3.072

6.  Inhibition of soluble epoxide hydrolase by trans-4- [4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid is protective against ischemia-reperfusion injury.

Authors:  Ketul R Chaudhary; Mohamed Abukhashim; Sung Hee Hwang; Bruce D Hammock; John M Seubert
Journal:  J Cardiovasc Pharmacol       Date:  2010-01       Impact factor: 3.105

7.  Anti-inflammatory effects of ω-3 polyunsaturated fatty acids and soluble epoxide hydrolase inhibitors in angiotensin-II-dependent hypertension.

Authors:  Arzu Ulu; Todd R Harris; Christophe Morisseau; Christina Miyabe; Hiromi Inoue; Gertrud Schuster; Hua Dong; Ana-Maria Iosif; Jun-Yan Liu; Robert H Weiss; Nipavan Chiamvimonvat; John D Imig; Bruce D Hammock
Journal:  J Cardiovasc Pharmacol       Date:  2013-09       Impact factor: 3.105

8.  Activation of microsomal epoxide hydrolase by interaction with cytochromes P450: kinetic analysis of the association and substrate-specific activation of epoxide hydrolase function.

Authors:  Ken-ichiro Taura Ki; Hideyuki Yamada; Eri Naito; Noritaka Ariyoshi; Masa-aki Mori Ma; Kazuta Oguri
Journal:  Arch Biochem Biophys       Date:  2002-06-15       Impact factor: 4.013

Review 9.  Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases.

Authors:  John D Imig; Bruce D Hammock
Journal:  Nat Rev Drug Discov       Date:  2009-10       Impact factor: 84.694

10.  Evidence for a complex formation between CYP2J5 and mEH in living cells by FRET analysis of membrane protein interaction in the endoplasmic reticulum (FAMPIR).

Authors:  Anette Carolina Orjuela Leon; Anne Marwosky; Michael Arand
Journal:  Arch Toxicol       Date:  2017-10-13       Impact factor: 5.153

View more
  27 in total

1.  Chiral lipidomics of monoepoxy and monohydroxy metabolites derived from long-chain polyunsaturated fatty acids.

Authors:  Maximilian Blum; Inci Dogan; Mirjam Karber; Michael Rothe; Wolf-Hagen Schunck
Journal:  J Lipid Res       Date:  2018-11-08       Impact factor: 5.922

Review 2.  Role of epoxy-fatty acids and epoxide hydrolases in the pathology of neuro-inflammation.

Authors:  Sean D Kodani; Christophe Morisseau
Journal:  Biochimie       Date:  2019-02-01       Impact factor: 4.079

Review 3.  Lipid mediators in immune regulation and resolution.

Authors:  Derek W Gilroy; David Bishop-Bailey
Journal:  Br J Pharmacol       Date:  2019-03-01       Impact factor: 8.739

4.  Development of potent inhibitors of the human microsomal epoxide hydrolase.

Authors:  Bogdan Barnych; Nalin Singh; Sophie Negrel; Yue Zhang; Damien Magis; Capucine Roux; Xiude Hua; Zhewen Ding; Christophe Morisseau; Dean J Tantillo; Justin B Siegel; Bruce D Hammock
Journal:  Eur J Med Chem       Date:  2020-03-13       Impact factor: 6.514

5.  Ephx2-gene deletion affects acetylcholine-induced relaxation in angiotensin-II infused mice: role of nitric oxide and CYP-epoxygenases.

Authors:  Ahmad Hanif; Matthew L Edin; Darryl C Zeldin; Mohammed A Nayeem
Journal:  Mol Cell Biochem       Date:  2019-12-04       Impact factor: 3.396

Review 6.  Lipokines and Thermogenesis.

Authors:  Matthew D Lynes; Sean D Kodani; Yu-Hua Tseng
Journal:  Endocrinology       Date:  2019-10-01       Impact factor: 4.736

Review 7.  Prospective for cytochrome P450 epoxygenase cardiovascular and renal therapeutics.

Authors:  John D Imig
Journal:  Pharmacol Ther       Date:  2018-06-30       Impact factor: 12.310

8.  Lipidomic profiling reveals soluble epoxide hydrolase as a therapeutic target of obesity-induced colonic inflammation.

Authors:  Weicang Wang; Jun Yang; Jianan Zhang; Yuxin Wang; Sung Hee Hwang; Weipeng Qi; Debin Wan; Daeyoung Kim; Jia Sun; Katherine Z Sanidad; Haixia Yang; Yeonhwa Park; Jun-Yan Liu; Xinfeng Zhao; Xiaohui Zheng; Zhenhua Liu; Bruce D Hammock; Guodong Zhang
Journal:  Proc Natl Acad Sci U S A       Date:  2018-05-01       Impact factor: 11.205

9.  Soluble epoxide hydrolase deficiency attenuates lipotoxic cardiomyopathy via upregulation of AMPK-mTORC mediated autophagy.

Authors:  Luyun Wang; Daqiang Zhao; Liangqiu Tang; Huihui Li; Zhaoyu Liu; Jingwei Gao; Matthew L Edin; Huanji Zhang; Kun Zhang; Jie Chen; Xinhong Zhu; Daowen Wang; Darryl C Zeldin; Bruce D Hammock; Jingfeng Wang; Hui Huang
Journal:  J Mol Cell Cardiol       Date:  2020-12-27       Impact factor: 5.000

10.  EPHX1 mutations cause a lipoatrophic diabetes syndrome due to impaired epoxide hydrolysis and increased cellular senescence.

Authors:  Jeremie Gautheron; Christophe Morisseau; Wendy K Chung; Jamila Zammouri; Martine Auclair; Genevieve Baujat; Emilie Capel; Celia Moulin; Yuxin Wang; Jun Yang; Bruce D Hammock; Barbara Cerame; Franck Phan; Bruno Fève; Corinne Vigouroux; Fabrizio Andreelli; Isabelle Jeru
Journal:  Elife       Date:  2021-08-03       Impact factor: 8.140

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.