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      Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid

      research-article
      a , * , b
      Biochimica et biophysica acta
      Inflammation, Cancer, Asthma, 5-Oxo-ETE, OXE receptor, 12-HETE

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          Abstract

          Arachidonic acid can be oxygenated by a variety of different enzymes, including lipoxygenases, cyclooxygenases, and cytochrome P450s, and can be converted to a complex mixture of oxygenated products as a result of lipid peroxidation. The initial products in these reactions are hydroperoxyeicosatetraenoic acids (HpETEs) and hydroxyeicosatetraenoic acids (HETEs). Oxoeicosatetraenoic acids (oxo-ETEs) can be formed by the actions of various dehydrogenases on HETEs or by dehydration of HpETEs. Although a large number of different HETEs and oxo-ETEs have been identified, this review will focus principally on 5-oxo-ETE, 5S-HETE, 12S-HETE, and 15S-HETE. Other related arachidonic acid metabolites will also be discussed in less detail. 5-Oxo-ETE is synthesized by oxidation of the 5-lipoxygenase product 5S-HETE by the selective enzyme, 5-hydroxyeicosanoid dehydrogenase. It actions are mediated by the selective OXE receptor, which is highly expressed on eosinophils, suggesting that it may be important in eosinophilic diseases such as asthma. 5-Oxo-ETE also appears to stimulate tumor cell proliferation and may also be involved in cancer. Highly selective and potent OXE receptor antagonists have recently become available and could help to clarify its pathophysiological role. The 12-lipoxygenase product 12S-HETE acts by the GPR31 receptor and promotes tumor cell proliferation and metastasis and could therefore be a promising target in cancer therapy. It may also be involved as a proinflammatory mediator in diabetes. In contrast, 15S-HETE may have a protective effect in cancer. In addition to GPCRs, higher concentration of HETEs and oxo-ETEs can activate peroxisome proliferator-activated receptors (PPARs) and could potentially regulate a variety of processes by this mechanism.

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          Author and article information

          Journal
          0217513
          1037
          Biochim Biophys Acta
          Biochim. Biophys. Acta
          Biochimica et biophysica acta
          0006-3002
          1878-2434
          16 November 2014
          29 October 2014
          April 2015
          01 December 2017
          : 1851
          : 4
          : 340-355
          Affiliations
          [a ]Meakins-Christie Laboratories, Department of Medicine, McGill University, 3626 St. Urbain Street, Montreal, Quebec H2X 2P2, Canada
          [b ]Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, USA
          Author notes
          [* ] Corresponding author: William S. Powell, Meakins-Christie Laboratories, McGill University, 3626 St. Urbain Street, Montreal, Quebec H2X 2P2, Canada, Telephone: 1-514-398-3864 ext. 094071#, William.Powell@ 123456McGill.ca
          Article
          PMC5710736 PMC5710736 5710736 nihpa642716
          10.1016/j.bbalip.2014.10.008
          5710736
          25449650
          62c6b2dc-2dab-4bdd-9ca6-67dc9f26771b
          History
          Categories
          Article

          Inflammation,12-HETE,OXE receptor,5-Oxo-ETE,Asthma,Cancer
          Inflammation, 12-HETE, OXE receptor, 5-Oxo-ETE, Asthma, Cancer

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