Literature DB >> 32894508

Epoxy Fatty Acids Are Promising Targets for Treatment of Pain, Cardiovascular Disease and Other Indications Characterized by Mitochondrial Dysfunction, Endoplasmic Stress and Inflammation.

Cindy McReynolds1,2, Christophe Morisseau1, Karen Wagner1,2, Bruce Hammock3.   

Abstract

Bioactive lipid mediators resulting from the metabolism of polyunsaturated fatty acids (PUFA) are controlled by many pathways that regulate the levels of these mediators and maintain homeostasis to prevent disease. PUFA metabolism is driven primarily through three pathways. Two pathways, the cyclooxygenase (COX) and lipoxygenase (LO) enzymatic pathways, form metabolites that are mostly inflammatory, while the third route of metabolism results from the oxidation by the cytochrome P450 enzymes to form hydroxylated PUFA and epoxide metabolites. These epoxygenated fatty acids (EpFA) demonstrate largely anti-inflammatory and beneficial properties, in contrast to the other metabolites formed from the degradation of PUFA. Dysregulation of these systems often leads to chronic disease. Pharmaceutical targets of disease focus on preventing the formation of inflammatory metabolites from the COX and LO pathways, while maintaining the EpFA and increasing their concentration in the body is seen as beneficial to treating and preventing disease. The soluble epoxide hydrolase (sEH) is the major route of metabolism of EpFA. Inhibiting its activity increases concentrations of beneficial EpFA, and often disease states correlate to mutations in the sEH enzyme that increase its activity and decrease the concentrations of EpFA in the body. Recent approaches to increasing EpFA include synthetic mimics that replicate biological activity of EpFA while preventing their metabolism, while other approaches focus on developing small molecule inhibitors to the sEH. Increasing EpFA concentrations in the body has demonstrated multiple beneficial effects in treating many diseases, including inflammatory and painful conditions, cardiovascular disease, neurological and disease of the central nervous system. Demonstration of efficacy in so many disease states can be explained by the fundamental mechanism that EpFA have of maintaining healthy microvasculature and preventing mitochondrial and endoplasmic reticulum stress. While there are no FDA approved methods that target the sEH or other enzymes responsible for metabolizing EpFA, current clinical efforts to test for efficacy by increasing EpFA that include inhibiting the sEH or administration of EpFA mimics that block metabolism are in progress.

Entities:  

Keywords:  Epoxide; Lipid metabolism; Oxylipin; PUFA; sEH

Mesh:

Substances:

Year:  2020        PMID: 32894508      PMCID: PMC7737916          DOI: 10.1007/978-3-030-50621-6_5

Source DB:  PubMed          Journal:  Adv Exp Med Biol        ISSN: 0065-2598            Impact factor:   2.622


  141 in total

Review 1.  Diet, endocannabinoids, and health.

Authors:  Bruce A Watkins
Journal:  Nutr Res       Date:  2019-06-15       Impact factor: 3.315

2.  Activity-based protein profiling reveals off-target proteins of the FAAH inhibitor BIA 10-2474.

Authors:  Annelot C M van Esbroeck; Antonius P A Janssen; Armand B Cognetta; Daisuke Ogasawara; Guy Shpak; Mark van der Kroeg; Vasudev Kantae; Marc P Baggelaar; Femke M S de Vrij; Hui Deng; Marco Allarà; Filomena Fezza; Zhanmin Lin; Tom van der Wel; Marjolein Soethoudt; Elliot D Mock; Hans den Dulk; Ilse L Baak; Bogdan I Florea; Giel Hendriks; Luciano De Petrocellis; Herman S Overkleeft; Thomas Hankemeier; Chris I De Zeeuw; Vincenzo Di Marzo; Mauro Maccarrone; Benjamin F Cravatt; Steven A Kushner; Mario van der Stelt
Journal:  Science       Date:  2017-06-09       Impact factor: 47.728

Review 3.  Engineering and application of enzymes for lipid modification, an update.

Authors:  Katja Zorn; Isabel Oroz-Guinea; Henrike Brundiek; Uwe T Bornscheuer
Journal:  Prog Lipid Res       Date:  2016-06-11       Impact factor: 16.195

4.  Alkyl 3,7,11-trimethyl-2,4-dodecadienoates, a new class of potent insect growth regulators with juvenile hormone activity.

Authors:  C A Henrick; G B Staal; J B Siddall
Journal:  J Agric Food Chem       Date:  1973 May-Jun       Impact factor: 5.279

5.  Metabolic products of soluble epoxide hydrolase are essential for monocyte chemotaxis to MCP-1 in vitro and in vivo.

Authors:  Suman Kundu; Talat Roome; Ashish Bhattacharjee; Kevin A Carnevale; Valentin P Yakubenko; Renliang Zhang; Sung Hee Hwang; Bruce D Hammock; Martha K Cathcart
Journal:  J Lipid Res       Date:  2012-11-15       Impact factor: 5.922

6.  Brain P450 epoxygenase activity is required for the antinociceptive effects of improgan, a nonopioid analgesic.

Authors:  Lindsay B Hough; Julia W Nalwalk; Jun Yang; Jennie L Conroy; Melissa A VanAlstine; Weizhu Yang; Joseph Gargano; Zhixing Shan; Shao-Zhong Zhang; Mark P Wentland; James G Phillips; Brian I Knapp; Jean M Bidlack; Obbe P Zuiderveld; Rob Leurs; Xinxin Ding
Journal:  Pain       Date:  2011-04       Impact factor: 6.961

7.  Cytochrome P4502S1: a novel monocyte/macrophage fatty acid epoxygenase in human atherosclerotic plaques.

Authors:  Timo Frömel; Karin Kohlstedt; Rüdiger Popp; Xiaoke Yin; Khader Awwad; Eduardo Barbosa-Sicard; Anita C Thomas; Ralf Lieberz; Manuel Mayr; Ingrid Fleming
Journal:  Basic Res Cardiol       Date:  2012-12-07       Impact factor: 17.165

Review 8.  Pro-resolving lipid mediators are leads for resolution physiology.

Authors:  Charles N Serhan
Journal:  Nature       Date:  2014-06-05       Impact factor: 49.962

Review 9.  Oxidation of marine omega-3 supplements and human health.

Authors:  Benjamin B Albert; David Cameron-Smith; Paul L Hofman; Wayne S Cutfield
Journal:  Biomed Res Int       Date:  2013-04-30       Impact factor: 3.411

10.  Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.

Authors:  Kin Sing Stephen Lee; Jun-Yan Liu; Karen M Wagner; Svetlana Pakhomova; Hua Dong; Christophe Morisseau; Samuel H Fu; Jun Yang; Peng Wang; Arzu Ulu; Christina A Mate; Long V Nguyen; Sung Hee Hwang; Matthew L Edin; Alexandria A Mara; Heike Wulff; Marcia E Newcomer; Darryl C Zeldin; Bruce D Hammock
Journal:  J Med Chem       Date:  2014-08-11       Impact factor: 7.446

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  14 in total

1.  The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms.

Authors:  Naoki Matsumoto; Nalin Singh; Kin Sing Lee; Bogdan Barnych; Christophe Morisseau; Bruce D Hammock
Journal:  Prostaglandins Other Lipid Mediat       Date:  2022-06-30       Impact factor: 3.813

2.  Species Differences in Metabolism of Soluble Epoxide Hydrolase Inhibitor, EC1728, Highlight the Importance of Clinically Relevant Screening Mechanisms in Drug Development.

Authors:  Cindy B McReynolds; Jun Yang; Alonso Guedes; Christophe Morisseau; Roberto Garcia; Heather Knych; Caitlin Tearney; Briana Hamamoto; Sung Hee Hwang; Karen Wagner; Bruce D Hammock
Journal:  Molecules       Date:  2021-08-19       Impact factor: 4.411

3.  Changes in the Left Ventricular Eicosanoid Profile in Human Dilated Cardiomyopathy.

Authors:  Deanna K Sosnowski; K Lockhart Jamieson; Ahmed M Darwesh; Hao Zhang; Hedieh Keshavarz-Bahaghighat; Robert Valencia; Anissa Viveiros; Matthew L Edin; Darryl C Zeldin; Gavin Y Oudit; John M Seubert
Journal:  Front Cardiovasc Med       Date:  2022-05-19

4.  A Soluble Epoxide Hydrolase Inhibitor, 1-TrifluoromethoxyPhenyl-3-(1-Propionylpiperidin-4-yl) Urea, Ameliorates Experimental Autoimmune Encephalomyelitis.

Authors:  Deepa Jonnalagadda; Debin Wan; Jerold Chun; Bruce D Hammock; Yasuyuki Kihara
Journal:  Int J Mol Sci       Date:  2021-04-28       Impact factor: 5.923

5.  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

6.  Relative Importance of Soluble and Microsomal Epoxide Hydrolases for the Hydrolysis of Epoxy-Fatty Acids in Human Tissues.

Authors:  Christophe Morisseau; Sean D Kodani; Shizuo G Kamita; Jun Yang; Kin Sing Stephen Lee; Bruce D Hammock
Journal:  Int J Mol Sci       Date:  2021-05-08       Impact factor: 5.923

7.  The Consequences of Soluble Epoxide Hydrolase Deletion on Tumorigenesis and Metastasis in a Mouse Model of Breast Cancer.

Authors:  Rushendhiran Kesavan; Timo Frömel; Sven Zukunft; Bernhard Brüne; Andreas Weigert; Ilka Wittig; Rüdiger Popp; Ingrid Fleming
Journal:  Int J Mol Sci       Date:  2021-07-01       Impact factor: 5.923

8.  2-(Piperidin-4-yl)acetamides as Potent Inhibitors of Soluble Epoxide Hydrolase with Anti-Inflammatory Activity.

Authors:  Juan Martín-López; Sandra Codony; Clara Bartra; Christophe Morisseau; María Isabel Loza; Coral Sanfeliu; Bruce D Hammock; José Brea; Santiago Vázquez
Journal:  Pharmaceuticals (Basel)       Date:  2021-12-17

9.  Differential Effects of 17,18-EEQ and 19,20-EDP Combined with Soluble Epoxide Hydrolase Inhibitor t-TUCB on Diet-Induced Obesity in Mice.

Authors:  Yang Yang; Xinyun Xu; Haoying Wu; Jun Yang; Jiangang Chen; Christophe Morisseau; Bruce D Hammock; Ahmed Bettaieb; Ling Zhao
Journal:  Int J Mol Sci       Date:  2021-07-31       Impact factor: 6.208

10.  Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.

Authors:  Sandra Codony; Caterina Pont; Christian Griñán-Ferré; Ania Di Pede-Mattatelli; Carla Calvó-Tusell; Ferran Feixas; Sílvia Osuna; Júlia Jarné-Ferrer; Marina Naldi; Manuela Bartolini; María Isabel Loza; José Brea; Belén Pérez; Clara Bartra; Coral Sanfeliu; Jordi Juárez-Jiménez; Christophe Morisseau; Bruce D Hammock; Mercè Pallàs; Santiago Vázquez; Diego Muñoz-Torrero
Journal:  J Med Chem       Date:  2022-03-10       Impact factor: 7.446

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