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Epoxyeicosatrienoic

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https://www.readbyqxmd.com/read/28440284/cyp2j2-and-its-metabolites-eets-attenuate-insulin-resistance-via-regulating-macrophage-polarization-in-adipose-tissue
#1
Meiyan Dai, Lujin Wu, Peihua Wang, Zheng Wen, Xizhen Xu, Dao Wen Wang
Macrophages in adipose tissue are associated with obesity-induced low-grade inflammation, which contributed to insulin resistance and the related metabolic diseases. Previous studies demonstrated the beneficial effects of epoxyeicosatrienoic acids (EETs) on metabolic disorders and inflammation. Here we investigated the effects of CYP2J2-EETs-sEH metabolic pathway on insulin resistance in mice and the potential mechanisms. High fat diet (HFD)-induced obesity caused metabolic dysfunction with more weight gain, elevated glucose and lipids levels, impaired glucose tolerance and insulin sensitivity, while increase in EETs level by rAAV-mediated CYP2J2 overexpression, administration of sEH inhibit TUPS or EETs infusion significantly attenuated these metabolic disorders...
April 25, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28411230/interaction-of-12-15-lipoxygenase-with-fatty-acids-alters-the-leukocyte-kinetics-leading-to-improved-post-myocardial-infarction-healing
#2
Ganesh V Halade, Vasundhara Kain, Kevin A Ingle, Sumanth D Prabhu
The metabolic transformation of fatty acids to form oxylipids using 12/15lipoxygenase (LOX) can promote either resolving or non-resolving inflammation. However, the mechanism of how 12/15LOX interacts with PUFA (polyunsaturated fatty acids) in post-myocardial infarction (MI) healing is unclear. Here, we reported the role of 12/15LOX in post-MI cardiac remodeling in a PUFA (10% w/w, 22 Kcal) enriched environment. Wild-type (WT; C57BL/6J) and 12/15LOX null (12/15LOX(-/-)) male mice of 8-12-weeks age were fed PUFA-enriched diet for 1 month and subjected to permanent coronary artery ligation...
April 14, 2017: American Journal of Physiology. Heart and Circulatory Physiology
https://www.readbyqxmd.com/read/28402977/molecular-mechanisms-leading-to-splanchnic-vasodilation-in-liver-cirrhosis
#3
Marco Di Pascoli, David Sacerdoti, Patrizia Pontisso, Paolo Angeli, Massimo Bolognesi
In liver cirrhosis, portal hypertension is a consequence of enhanced intrahepatic vascular resistance and portal blood flow. Significant vasodilation in the arterial splanchnic district is crucial for an increase in portal flow. In this pathological condition, increased levels of circulating endogenous vasodilators, including nitric oxide, prostacyclin, carbon monoxide, epoxyeicosatrienoic acids, glucagon, endogenous cannabinoids, and adrenomedullin, and a decreased vascular response to vasoconstrictors are the main mechanisms underlying splanchnic vasodilation...
April 13, 2017: Journal of Vascular Research
https://www.readbyqxmd.com/read/28396419/cyclooxygenase-derived-proangiogenic-metabolites-of-epoxyeicosatrienoic-acids
#4
Amy A Rand, Bogdan Barnych, Christophe Morisseau, Tomas Cajka, Kin Sing Stephen Lee, Dipak Panigrahy, Bruce D Hammock
Arachidonic acid (ARA) is metabolized by cyclooxygenase (COX) and cytochrome P450 to produce proangiogenic metabolites. Specifically, epoxyeicosatrienoic acids (EETs) produced from the P450 pathway are angiogenic, inducing cancer tumor growth. A previous study showed that inhibiting soluble epoxide hydrolase (sEH) increased EET concentration and mildly promoted tumor growth. However, inhibiting both sEH and COX led to a dramatic decrease in tumor growth, suggesting that the contribution of EETs to angiogenesis and subsequent tumor growth may be attributed to downstream metabolites formed by COX...
April 10, 2017: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/28384353/generation-and-characterization-of-epoxide-hydrolase-3-ephx3-deficient-mice
#5
Samantha L Hoopes, Artiom Gruzdev, Matthew L Edin, Joan P Graves, J Alyce Bradbury, Gordon P Flake, Fred B Lih, Laura M DeGraff, Darryl C Zeldin
Cytochrome P450 (CYP) epoxygenases metabolize arachidonic acid into epoxyeicosatrienoic acids (EETs), which play an important role in blood pressure regulation, protection against ischemia-reperfusion injury, angiogenesis, and inflammation. Epoxide hydrolases metabolize EETs to their corresponding diols (dihydroxyeicosatrienoic acids; DHETs) which are biologically less active. Microsomal epoxide hydrolase (EPHX1, mEH) and soluble epoxide hydrolase (EPHX2, sEH) were identified >30 years ago and are capable of hydrolyzing EETs to DHETs...
2017: PloS One
https://www.readbyqxmd.com/read/28374982/angiotensin-ii-receptor-blockers-inhibit-the-generation-of-epoxyeicosatrienoic-acid-from-arachidonic-acid-in-recombinant-cyp2c9-cyp2j2-and-human-liver-microsomes
#6
Asuna Senda, Yuji Mukai, Toru Hayakawa, Yuka Kato, Erik Eliasson, Anders Rane, Takaki Toda, Nobuo Inotsume
Cytochrome P450 (CYP) 2C9, CYP2C8 and CYP2J2 enzymes, which metabolize arachidonic acid to epoxyeicosatrienoic acids (EETs), have cardioprotective effects including anti-inflammation and vasodilation. We have recently shown that some angiotensin II receptor blockers (ARBs) may inhibit AA metabolism via CYP2C8. Using recombinant CYP2C9, CYP2J2, and human liver microsomes (HLMs), the aim was now to compare the ability of six different clinically used ARBs to inhibit AA metabolism in vitro. The rank order of the ARBs for the 50% inhibitory concentration (IC50 ) of AA metabolism was losartan < telmisartan < irbesartan < candesartan < olmesartan < valsartan via CYP2C9, and telmisartan < irbesartan < olmesartan < losartan < candesartan and valsartan via CYP2J2...
April 4, 2017: Basic & Clinical Pharmacology & Toxicology
https://www.readbyqxmd.com/read/28356494/soluble-epoxide-hydrolase-pharmacological-inhibition-decreases-alveolar-bone-loss-by-modulating-host-inflammatory-response-rank-related-signaling-er-stress-and-apoptosis
#7
Carlos A Trindade da Silva, Ahmed Bettaieb, Marcelo H Napimoga, Kin Sing Stephen Lee, Bora Inceoglu, Carlos Ueira-Vieira, Donald Bruun, Sumanta K Goswami, Fawaz G Haj, Bruce D Hammock
Epoxyeicosatrienoic acids (EETs), metabolites of arachidonic acid derived from the cytochrome P450 (CYP450) enzymes, are mainly metabolized by soluble epoxide hydrolase (sEH) to their corresponding diols. EETs but not their diols, have anti-inflammatory properties and inhibition of sEH might provide protective effects against inflammatory bone loss. Thus, in the present study, we tested the selective sEH inhibitor, 1-trifluoromethoxyphenyl-3-(1-propionylpiperidin-4-yl) urea (TPPU) in a mouse model of periodontitis induced by infection with A...
March 29, 2017: Journal of Pharmacology and Experimental Therapeutics
https://www.readbyqxmd.com/read/28352940/cytochrome-p450-epoxygenase-derived-epoxyeicosatrienoic-acids-contribute-to-insulin-sensitivity-in-mice-and-in-humans
#8
Mahesha H Gangadhariah, Blake W Dieckmann, Louise Lantier, Li Kang, David H Wasserman, Manuel Chiusa, Charles F Caskey, Jaime Dickerson, Pengcheng Luo, Jorge L Gamboa, Jorge H Capdevila, John D Imig, Chang Yu, Ambra Pozzi, James M Luther
AIMS/HYPOTHESIS: Insulin resistance is frequently associated with hypertension and type 2 diabetes. The cytochrome P450 (CYP) arachidonic acid epoxygenases (CYP2C, CYP2J) and their epoxyeicosatrienoic acid (EET) products lower blood pressure and may also improve glucose homeostasis. However, the direct contribution of endogenous EET production on insulin sensitivity has not been previously investigated. In this study, we tested the hypothesis that endogenous CYP2C-derived EETs alter insulin sensitivity by analysing mice lacking CYP2C44, a major EET producing enzyme, and by testing the association of plasma EETs with insulin sensitivity in humans...
March 28, 2017: Diabetologia
https://www.readbyqxmd.com/read/28332266/11-12-epoxyeicosatrienoic-acid-induces-vasodilator-response-in-the-rat-perfused-mesenteric-vasculature
#9
S M Bihzad, M H M Yousif
Epoxyeicosatrienoic acids (EETs) are endogenous ligands that undergo hydrolysis by soluble epoxide hydrolase (sEH). The responses of 11, 12-EET in comparison with other vasodilator agonists including carbachol and sodium nitroprusside (SNP) were investigated. The effect of 1-cyclohexyl-3-dodecyl urea (CDU), a sEH, was tested on the vasodilator effect induced by 11, 12-EET in the perfused mesenteric beds isolated from normo-glycaemic and type-1 STZ-diabetic rats. In the perfused mesenteric beds of control and diabetic animals, 11, 12-EET produced vasodilation in a dose-dependent manner...
January 2017: Autonomic & Autacoid Pharmacology
https://www.readbyqxmd.com/read/28328948/vascular-endothelial-overexpression-of-human-cyp2j2-tie2-cyp2j2-tr-modulates-cardiac-oxylipin-profiles-and-enhances-coronary-reactive-hyperemia-in-mice
#10
Ahmad Hanif, Matthew L Edin, Darryl C Zeldin, Christophe Morisseau, John R Falck, Mohammed A Nayeem
Arachidonic acid is metabolized to epoxyeicosatrienoic acids (EETs) by cytochrome (CYP) P450 epoxygenases, and to ω-terminal hydroxyeicosatetraenoic acids (HETEs) by ω-hydroxylases. EETs and HETEs often have opposite biologic effects; EETs are vasodilatory and protect against ischemia/reperfusion injury, while ω-terminal HETEs are vasoconstrictive and cause vascular dysfunction. Other oxylipins, such as epoxyoctadecaenoic acids (EpOMEs), hydroxyoctadecadienoic acids (HODEs), and prostanoids also have varied vascular effects...
2017: PloS One
https://www.readbyqxmd.com/read/28319086/cytochrome-p450-cyp-epoxygenases-as-potential-targets-in-the-management-of-impaired-diabetic-wound-healing
#11
Huichen Zhao, Jicui Chen, Jiachao Chai, Yuchao Zhang, Cong Yu, Zhe Pan, Peng Gao, Chen Zong, Qingbo Guan, Yuqin Fu, Yuantao Liu
Epoxyeicosatrienoic acids (EETs) are the epoxidation products of arachidonic acid catalyzed by cytochrome P450 (CYP) epoxygenases, which possess multiple biological activities. In the present study, we aimed to explore the role and effects of CYP epoxygenases/EETs in wound healing in ob/ob mice. Full-thickness skin dorsal wounds were made on ob/ob mice and C57BL/6 control mice. The mRNA and protein expression of CYP epoxygenases were determined in granulation tissues of wounds. Effects of EETs on wound healing were evaluated...
March 20, 2017: Laboratory Investigation; a Journal of Technical Methods and Pathology
https://www.readbyqxmd.com/read/28298143/p450-eicosanoids-and-reactive-oxygen-species-interplay-in-brain-injury-and-neuroprotection
#12
Xuehong Liu, Catherine M Davis, Nabil J Alkayed
SIGNIFICANCE: Eicosanoids are endogenous lipid mediators that play important roles in brain function and disease. Acute brain injury such as that which occurs in stroke and traumatic brain injury increases the formation of eicosanoids, which, in turn, exacerbate or diminish injury. In chronic neurodegenerative diseases such as Alzheimer's disease and vascular dementia (VD), eicosanoid synthetic and metabolizing enzymes are altered, disrupting the balance between neuroprotective and neurotoxic eicosanoids...
April 20, 2017: Antioxidants & Redox Signaling
https://www.readbyqxmd.com/read/28293507/soluble-epoxide-hydrolase-inhibition-and-epoxyeicosatrienoic-acid-treatment-improve-vascularization-of-engineered-skin-substitutes
#13
Dorothy M Supp, Jennifer M Hahn, Kevin L McFarland, Kelly A Combs, Kin Sing Stephen Lee, Bora Inceoglu, Debin Wan, Steven T Boyce, Bruce D Hammock
BACKGROUND: Autologous engineered skin substitutes comprised of keratinocytes, fibroblasts, and biopolymers can serve as an adjunctive treatment for excised burns. However, engineered skin lacks a vascular plexus at the time of grafting, leading to slower vascularization and reduced rates of engraftment compared with autograft. Hypothetically, vascularization of engineered skin grafts can be improved by treatment with proangiogenic agents at the time of grafting. Epoxyeicosatrienoic acids (EETs) are cytochrome P450 metabolites of arachidonic acid that are inactivated by soluble epoxide hydrolase (sEH)...
December 2016: Plastic and Reconstructive Surgery. Global Open
https://www.readbyqxmd.com/read/28237650/inhibition-and-inactivation-of-human-cyp2j2-implications-in-cardiac-pathophysiology-and-opportunities-in-cancer-therapy
#14
REVIEW
Aneesh Karkhanis, Yanjun Hong, Eric Chun Yong Chan
Extrahepatic cytochrome P450 enzymes (CYP450) are pivotal in the metabolism of endogenous substrates and xenobiotics. CYP2J2 is a major cardiac CYP450 and primarily metabolizes polyunsaturated fatty acids such as arachidonic acid to cardioactive epoxyeicosatrienoic acids. Due to its role in endobiotic metabolism, CYP2J2 has been actively studied in recent years with the focus on its biological functions in cardiac pathophysiology. Additionally, CYP2J2 metabolizes a number of xenobiotics such as astemizole and terfenadine and is potently inhibited by danazol and telmisartan...
February 23, 2017: Biochemical Pharmacology
https://www.readbyqxmd.com/read/28237619/glutamate-affects-the-production-of-epoxyeicosanoids-within-the-brain-the-up-regulation-of-brain-cyp2j-through-the-mapk-creb-signaling-pathway
#15
Mingzhou Liu, Quanfei Zhu, Jinhua Wu, Xuming Yu, Mingbai Hu, Xianfei Xie, Zheqiong Yang, Jing Yang, Yu-Qi Feng, Jiang Yue
Glutamate is the major excitatory neurotransmitter in the brain, and chronic glutamate excitotoxicity has been thought to be involved in numerous neurodegenerative diseases. We investigated the effects of glutamate at concentrations lower than the usual extrasynaptic concentrations on the production of epoxyeicosanoids mediated by brain CYP2J. Glutamate increased CYP2J2 mRNA levels in astrocytes in a dose-dependent manner, while an antagonist of the metabotropic glutamate receptor subtype 5 (mGlu5 receptor) attenuated the glutamate-induced increases in CYP2J2 levels by glutamate...
April 15, 2017: Toxicology
https://www.readbyqxmd.com/read/28218273/discovery-of-the-first-dual-inhibitor-of-the-5-lipoxygenase-activating-protein-and-soluble-epoxide-hydrolase-using-pharmacophore-based-virtual-screening
#16
Veronika Temml, Ulrike Garscha, Erik Romp, Gregor Schubert, Jana Gerstmeier, Zsofia Kutil, Barbara Matuszczak, Birgit Waltenberger, Hermann Stuppner, Oliver Werz, Daniela Schuster
Leukotrienes (LTs) are pro-inflammatory lipid mediators derived from arachidonic acid (AA) with roles in inflammatory and allergic diseases. The biosynthesis of LTs is initiated by transfer of AA via the 5-lipoxygenase-activating protein (FLAP) to 5-lipoxygenase (5-LO). FLAP inhibition abolishes LT formation exerting anti-inflammatory effects. The soluble epoxide hydrolase (sEH) converts AA-derived anti-inflammatory epoxyeicosatrienoic acids (EETs) to dihydroxyeicosatetraenoic acids (di-HETEs). Its inhibition consequently also counteracts inflammation...
February 20, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28209804/long-chain-acyl-coa-synthetase-isoforms-differ-in-preferences-for-eicosanoid-species-and-long-chain-fatty-acids
#17
Eric L Klett, Shufen Chen, Alekhya Yechoor, Fred B Lih, Rosalind A Coleman
Because the signaling eicosanoids, epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids (HETEs), are esterified to membrane phospholipids, we asked which long-chain acyl-CoA synthetase (ACSL) isoforms would activate these molecules and whether the apparent fatty acid substrate preferences of each ACSL isoform might differ depending on whether it was assayed in mammalian cell membranes or as a purified bacterial recombinant protein. We found that all five ACSL isoforms were able to use EETs and HETEs as substrates and showed by LC-MS that ACSLs produce EET-CoAs...
February 16, 2017: Journal of Lipid Research
https://www.readbyqxmd.com/read/28140329/the-role-of-cytochrome-p450-epoxygenases-soluble-epoxide-hydrolase-and-epoxyeicosatrienoic-acids-in-metabolic-diseases
#18
REVIEW
Xizhen Xu, Rui Li, Guangzhi Chen, Samantha L Hoopes, Darryl C Zeldin, Dao Wen Wang
Metabolic diseases are associated with an increased risk of developing cardiovascular disease. The features comprising metabolic diseases include obesity, insulin resistance, hyperglycemia, hyperlipidemia, and hypertension. Recent evidence has emerged showcasing a role for cytochrome P450 epoxygenases, soluble epoxide hydrolase, and epoxyeicosatrienoic acids (EETs) in the development and progression of metabolic diseases. This review discusses the current knowledge related to the modulation of cytochrome P450 epoxygenases and soluble epoxide hydrolase to alter concentrations of biologically active EETs, resulting in effects on insulin resistance, lipid metabolism, obesity, and diabetes...
November 2016: Advances in Nutrition
https://www.readbyqxmd.com/read/28111064/a-rapid-uplc-ms-ms-assay-for-eicosanoids-in-human-plasma-application-to-evaluate-niacin-responsivity
#19
Tricia M Miller, Samuel M Poloyac, Kacey B Anderson, Brooke L Waddell, Erik Messamore, Jeffrey K Yao
A rapid and sensitive method using ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was developed to simultaneously quantify hydroxyeicosatetraenoic (HETE), dihydroxyeicosatrienoic (DiHETrE), epoxyeicosatrienoic acid (EET), and prostaglandin metabolites of arachidonic acid in human plasma. Sample preparation consisted of solid phase extraction with Oasis HLB (30mg) cartridges for all metabolites. Separation of HETEs, EETs, and DiHETrEs was achieved on an Acquity UPLC BEH C18, 1...
January 18, 2017: Prostaglandins, Leukotrienes, and Essential Fatty Acids
https://www.readbyqxmd.com/read/28104457/genetic-deletion-of-soluble-epoxide-hydrolase-provides-cardioprotective-responses-following-myocardial-infarction-in-aged-mice
#20
REVIEW
K Lockhart Jamieson, Victor Samokhvalov, Maria Akhnokh, Kyra Lee, Woo Jung Cho, Abhijit Takawale, Xiuhua Wang, Zamaneh Kassiri, John M Seubert
BACKGROUND: Pathophysiological responses, including cardiovascular complications, often alter with age. Cardioprotective effects of epoxyeicosatrienoic acids (EETs) toward acute myocardial ischemia-reperfusion injury have been well documented. However, biological relevance of EET-evoked cardioprotection in the ageing myocardium remains unknown. EETs are metabolized to less active metabolites by the enzyme soluble epoxide hydrolase (sEH). This study uses permanent occlusion of the left anterior descending artery (LAD) in young and aged sEH null and WT mice to compare cardiac and mitochondrial function following ischemic injury...
January 16, 2017: Prostaglandins & Other Lipid Mediators
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