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Epoxyeicosatrienoic

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https://www.readbyqxmd.com/read/28526610/11-12-epoxyeicosatrienoic-acid-11-12-eet-reduces-excitability-and-excitatory-transmission-in-the-hippocampus
#1
Nandkishor K Mule, Anette C Orjuela Leon, John R Falck, Michael Arand, Anne Marowsky
Recent studies suggest a role for the arachidonic acid-derived epoxyeicosatrienoic acids (EETs) in attenuating epileptic seizures. However, their effect on neurotransmission has never been investigated in detail. Here, we studied how 11,12- and 14,15 EET affect excitability and excitatory neurotransmission in mouse hippocampus. 11,12 EET (2 μM), but not 14,15 EET (2 μM), induced the opening of a hyperpolarizing K(+) conductance in CA1 pyramidal cells. This action could be blocked by BaCl2, the G protein blocker GDPβ-S and the GIRK1/4 blocker tertiapin Q and the channel was thus identified as a GIRK channel...
May 16, 2017: Neuropharmacology
https://www.readbyqxmd.com/read/28488585/eets-reduces-lps-induced-hyperpermeability-by-targeting-grp78-mediated-src-activation-and-subsequent-rho-rock-signaling-pathway
#2
Ruolan Dong, Danli Hu, Yan Yang, Zhihui Chen, Menglu Fu, Dao Wen Wang, Xizhen Xu, Ling Tu
Integrity of endothelial barrier is a determinant of the prognosis in the acute lung injury caused by sepsis. The epoxyeicosatrienoic acids (EETs), metabolites of arachidonic acid, exhibit protective effects in various pathogenic states, however, whether EETs play a role in endothelial barrier enhancement and the involved mechanisms remain to be investigated. Here, we show that increased EETs level by endothelial specific cytochrome P450 epoxygenase 2J2 over-expression and soluble epoxide hydrolase (sEH) inhibitor TPPU reduced lipopolysaccharide-induced endothelial hyper-permeability in vivo, accompanied by improved survival of septic mice...
April 21, 2017: Oncotarget
https://www.readbyqxmd.com/read/28473204/inhibition-of-soluble-epoxide-hydrolase-reduces-portal-pressure-by-protecting-mesenteric-artery-myogenic-responses-in-cirrhotic-rats
#3
Yijun Huang, Jun Qin, Dong Sun, Houli Jiang, Lei Zheng, Yue He, Liang Gui, Binbin Qian, Chihao Zhang, Meng Luo
Hyperdynamic circulation contributes to the progress of portal hypertension in liver cirrhosis. We investigated the effects of soluble epoxide hydrolase (sEH) inhibition on portal pressure and the myogenic response of mesenteric arteries isolated from cirrhotic rats using the sEH inhibitor t-TUCB (trans-4-{4-[3-(4-trifluoromethoxyphenyl)-ureido] cyclohexyloxy} benzoic acid). Cirrhotic tissues had a higher ratio of epoxyeicosatrienoic acids (EETs) to dihydroxyeicosatrienoic acids (DHETs) following increased CYP2C11 expression, which may be a protective response...
May 1, 2017: Prostaglandins & Other Lipid Mediators
https://www.readbyqxmd.com/read/28470279/synthesis-of-cyclooxygenase-metabolites-of-8-9-epoxyeicosatrienoic-acid-eet-11-and-15-hydroxy-8-9-eets
#4
Bogdan Barnych, Amy A Rand, Tomas Cajka, Kin Sing Stephen Lee, Bruce D Hammock
COX metabolites of 8,9-EET, previously observed as potent mitogenic lipid mediators, were synthesized for the first time by using two synthetic approaches. These synthetic materials allow for structural confirmation of COX metabolites of 8,9-EET and further study of their biological roles.
May 23, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28454544/attenuation-of-acute-lung-injury-in-a-rat-model-by-semen-cassiae
#5
Xiuqing Chen, Xianming Zhang, Jie Zhang, Yang Gao, Zhaohui Yang, Shanshan Li, Haiwen Dai
BACKGROUND: Acute lung injury (ALI) is an inflammatory disorder. Semen Cassiae has potent anti-inflammatory activities. The aim of our study was to investigate whether Semen Cassiae plays a protective effect on lipopolysaccharide (LPS)-induced ALI and, if so, to elucidate its potential mechanism. METHODS: Male Sprague-Dawley rat lungs were injured by intratracheal instillation of LPS. Rats were treated with Semen Cassiae or vehicle 3 h after LPS challenge. Samples were harvested 24 h post-LPS administration...
April 28, 2017: BMC Complementary and Alternative Medicine
https://www.readbyqxmd.com/read/28450284/eets-promote-hypoxic-pulmonary-vasoconstriction-via-constrictor-prostanoids
#6
Sharath Kandhi, Bin Zhang, Ghezal Froogh, Jun Qin, Norah Alruwali, Yicong Le, Yang-Ming Yang, Sung Hee Hwang, Bruce D Hammock, Michael S Wolin, An Huang, Dong Sun
To test the hypothesis that epoxyeicosatrienoic acids (EETs) facilitate pulmonary responses to hypoxia, male wild type (WT) and soluble epoxide hydrolase knockout (sEH-KO) mice, and WT mice chronically fed a sEH inhibitor (t-TUCB; 1mg/kg/day) were used. Right ventricular systolic pressure (RVSP) was recorded under control and hypoxic conditions. The control RVSP was comparable among all groups. However, hypoxia elicited increases in RVSP in all groups with predominance in sEH-KO and t-TUCB-treated mice. 14,15-EEZE (EET antagonist) attenuated the hypoxia-induced greater elevation of RVSP in sEH-deficient mice, suggesting an EET-mediated increment...
April 27, 2017: American Journal of Physiology. Lung Cellular and Molecular Physiology
https://www.readbyqxmd.com/read/28440284/cyp2j2-and-its-metabolites-eets-attenuate-insulin-resistance-via-regulating-macrophage-polarization-in-adipose-tissue
#7
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
#8
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
#9
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...
2017: Journal of Vascular Research
https://www.readbyqxmd.com/read/28396419/cyclooxygenase-derived-proangiogenic-metabolites-of-epoxyeicosatrienoic-acids
#10
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 25, 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
#11
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
#12
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-endoplasmic-reticulum-stress-and-apoptosis
#13
Carlos Antonio Trindade-da-Silva, Ahmed Bettaieb, Marcelo Henrique Napimoga, Kin Sing Stephen Lee, Bora Inceoglu, Carlos Ueira-Vieira, Donald Bruun, Sumanta Kumar Goswami, Fawaz G Haj, Bruce D Hammock
Epoxyeicosatrienoic acids (EETs), metabolites of arachidonic acid derived from the cytochrome P450 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 Aggregatibacter actinomycetemcomitans Oral treatment of wild-type mice with TPPU and sEH knockout (KO) animals showed reduced bone loss induced by A...
June 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
#14
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...
June 2017: Diabetologia
https://www.readbyqxmd.com/read/28332266/11-12-epoxyeicosatrienoic-acid-induces-vasodilator-response-in-the-rat-perfused-mesenteric-vasculature
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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
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