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Epoxide hydrolase

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https://www.readbyqxmd.com/read/28642117/soluble-epoxide-hydrolase-as-a-therapeutic-target-for-pain-inflammatory-and-neurodegenerative-diseases
#1
REVIEW
Karen M Wagner, Cindy B McReynolds, William K Schmidt, Bruce D Hammock
Eicosanoids are biologically active lipid signaling molecules derived from polyunsaturated fatty acids. Many of the actions of eicosanoid metabolites formed by cyclooxygenase and lipoxygenase enzymes have been characterized, however, the epoxy-fatty acids (EpFAs) formed by cytochrome P450 enzymes are newly described by comparison. The EpFA metabolites modulate a diverse set of physiologic functions that include inflammation and nociception among others. Regulation of EpFAs occurs primarily via release, biosynthesis and enzymatic transformation by the soluble epoxide hydrolase (sEH)...
June 19, 2017: Pharmacology & Therapeutics
https://www.readbyqxmd.com/read/28642035/improving-the-efficacy-of-hormone-therapy-in-breast-cancer-the-role-ofcholesterol-metabolism-in-serm-mediated-autophagy-cell-differentiation-and-death
#2
REVIEW
Julie Leignadier, Florence Dalenc, Marc Poirot, Sandrine Silvente-Poirot
Breast cancer (BC) is one of the most common female cancers in the world, with estrogen receptor (ER)-positive BC the most frequent subtype. Tamoxifen (Tam) is an effective drug that competitively binds to the ER and is routinely used for the treatment of ER-positive BC. However, a number of ER-positive BC do not respond to Tam treatment and acquired resistance is often observed, constituting a major challenge for extending patient life expectancy. The mechanisms responsible for these treatment failures remain unclear, indicating the requirement for other targets and better predictors for patient response to Tam...
June 19, 2017: Biochemical Pharmacology
https://www.readbyqxmd.com/read/28600384/oxetane-substrates-of-human-microsomal-epoxide-hydrolase
#3
Francesca Toselli, Marlene Fredenwall, Peder Svensson, Xue-Qing Li, Anders Johansson, Lars Weidolf, Martin A Hayes
Oxetanyl building blocks are increasingly used in drug discovery because of the improved drug-like properties they confer on drug candidates, yet little is currently known about their biotransformation. A series of oxetane-containing analogues was studied and we provide the first direct evidence of oxetane hydrolysis by human recombinant microsomal epoxide hydrolase (mEH). Incubations with human liver fractions and hepatocytes were performed with and without inhibitors of P450s, mEH and soluble EH (sEH). Reaction dependence on NADPH was investigated in subcellular fractions...
June 9, 2017: Drug Metabolism and Disposition: the Biological Fate of Chemicals
https://www.readbyqxmd.com/read/28593475/functional-metagenomics-of-oil-impacted-mangrove-sediments-reveals-high-abundance-of-hydrolases-of-biotechnological-interest
#4
Júlia Ronzella Ottoni, Lucélia Cabral, Sanderson Tarciso Pereira de Sousa, Gileno Vieira Lacerda Júnior, Daniela Ferreira Domingos, Fábio Lino Soares Junior, Mylenne Calciolari Pinheiro da Silva, Joelma Marcon, Armando Cavalcante Franco Dias, Itamar Soares de Melo, Anete Pereira de Souza, Fernando Dini Andreote, Valéria Maia de Oliveira
Mangroves are located in coastal wetlands and are susceptible to the consequences of oil spills, what may threaten the diversity of microorganisms responsible for the nutrient cycling and the consequent ecosystem functioning. Previous reports show that high concentration of oil favors the incidence of epoxide hydrolases and haloalkane dehalogenases in mangroves. This finding has guided the goals of this study in an attempt to broaden the analysis to other hydrolases and thereby verify whether oil contamination interferes with the prevalence of particular hydrolases and their assigned microorganisms...
July 2017: World Journal of Microbiology & Biotechnology
https://www.readbyqxmd.com/read/28583889/a-diet-rich-in-omega-3-fatty-acids-enhances-expression-of-soluble-epoxide-hydrolase-in-murine-brain
#5
Annika Irmgard Ostermann, Martina Reutzel, Nicole Hartung, Nicole Franke, Laura Kutzner, Kirsten Schoenfeld, Karsten-Henrich Weylandt, Gunter Peter Eckert, Nils Helge Schebb
Several studies suggest that intake of omega-3 polyunsaturated fatty acids (n3-PUFA) beneficially influences cognitive function. However, effects on the adult brain are not clear. Little is known about the impact of dietary intervention on the fatty acid profile in adult brain, the modulation in the expression of enzymes involved in fatty acid biosynthesis and metabolism as well as changes in resulting oxylipins. These questions were addressed in the present study in two independent n3-PUFA feeding experiments in mice...
June 2, 2017: Prostaglandins & Other Lipid Mediators
https://www.readbyqxmd.com/read/28559906/drawing-links-from-transcriptome-to-metabolites-the-evolution-of-aroma-in-the-ripening-berry-of-moscato-bianco-vitis-vinifera-l
#6
Laura Costantini, Christian D Kappel, Massimiliano Trenti, Juri Battilana, Francesco Emanuelli, Maddalena Sordo, Marco Moretto, Céline Camps, Roberto Larcher, Serge Delrot, Maria S Grando
Monoterpenes confer typical floral notes to "Muscat" grapevine varieties and, to a lesser extent, to other aromatic non-Muscat varieties. Previous studies have led to the identification and functional characterization of some enzymes and genes in this pathway. However, the underlying genetic map is still far from being complete. For example, the specific steps of monoterpene metabolism and its regulation are largely unknown. With the aim of identifying new candidates for the missing links, we applied an integrative functional genomics approach based on the targeted metabolic and genome-wide transcript profiling of Moscato Bianco ripening berries...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/28558206/inhibition-potential-of-cycloartane-type-glycosides-from-the-roots-of-cimicifuga-dahurica-against-soluble-epoxide-hydrolase
#7
Nguyen Phuong Thao, Bui Thi Thuy Luyen, Ji Sun Lee, Jang Hoon Kim, Nguyen Tien Dat, Young Ho Kim
A phytochemical assay-guided fractionation of the 95% ethanol extract of Cimicifuga dahurica roots afforded 29 9,19-cycloartane triterpenoid glycosides, including the new cimiricasides A-F (1-6). The structures of 1-6 were established using contemporary NMR methods and from the HRESIMS data, and the sugar moiety in each case was confirmed by acid hydrolysis and subsequent GC/MS analysis. Compounds 2, 4, 5, 7-9, 18, 25, and 29 showed soluble epoxide hydrolase inhibitory effects with IC50 values of 0.4 ± 0.1 to 24...
May 30, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28554594/improvement-of-5-6%C3%AE-epoxycholesterol-5-6%C3%AE-epoxycholesterol-cholestane-3%C3%AE-5%C3%AE-6%C3%AE-triol-and-6-oxo-cholestan-3%C3%AE-5%C3%AE-diol-recovery-for-quantification-by-gc-ms
#8
Regis Soules, Emmanuel Noguer, Luigi Iuliano, Chiara Zerbinati, Julie Leignadier, Arnaud Rives, Philippe de Medina, Sandrine Silvente-Poirot, Marc Poirot
5,6α-epoxycholesterol (5,6α-EC) and 5,6β-epoxycholesterol (5,6β-EC) are oxysterols involved in the anticancer pharmacology of the widely used antitumor drug tamoxifen. They are both metabolized into cholestane-3β,5α,6β-triol (CT) by the cholesterol-5,6-epoxide hydrolase (ChEH) enzyme, and CT is metabolized by an as-yet uncharacterized enzyme into 6-oxo-cholestan-3β,5α-diol (OCDO). A recent feasibility study showed that the 5,6-ECs may represent surrogate markers of tamoxifen activity in breast cancer patients undergoing endocrine therapy, thus there is a growing interest in their accurate quantification...
May 26, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28552948/association-of-gain-of-function-ephx2-polymorphism-lys55arg-with-acute-kidney-injury-following-cardiac-surgery
#9
Megan M Shuey, Frederic T Billings, Shouzou Wei, Ginger L Milne, Hui Nian, Chang Yu, Nancy J Brown
Twenty to thirty percent of patients undergoing cardiac surgery develop acute kidney injury (AKI). In mice, inhibition of soluble epoxide hydrolase (sEH) attenuates renal injury following ischemia-reperfusion. We tested the hypothesis that functional variants of EPHX2, encoding sEH, are associated with AKI after cardiac surgery. We genotyped patients in two independent cardiac surgery cohorts for functional EPHX2 polymorphisms, Lys55Arg and Arg287Gln, and determined AKI using Acute Kidney Injury Network criteria...
2017: PloS One
https://www.readbyqxmd.com/read/28536442/characterization-of-juvenile-hormone-related-genes-regulating-cantharidin-biosynthesis-in-epicauta-chinensis
#10
Ming Jiang, Shumin Lü, Yalin Zhang
Cantharidin is a defensive toxin biosynthesized by blister beetles. It is well known for medical applications and toxicity. However, the biosynthesis process of cantharidin is still not well understood. In the present study, three genes (methyl farnesoate epoxidase (EcMFE), juvenile hormone acid O-methyltransferase (EcJHAMT) and juvenile hormone epoxide hydrolase (EcJHEH)) were identified from Epicauta chinensis. The temporal and spatial expression patterns of these three genes revealed that the expression levels of EcMFE and EcJHEH were high in the first instar larval stage of E...
May 23, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28535182/characterization-of-liver-injury-oval-cell-proliferation-and-cholangiocarcinogenesis-in-glutathione-s-transferase-a3-knockout-mice
#11
Dana R Crawford, Zoran Ilic, Ian Guest, Ginger L Milne, John D Hayes, Stewart Sell
We recently generated glutathione S-transferase (GST) A3 knockout (KO) mice as a novel model to study the risk factors for liver cancer. GSTA3 KO mice are sensitive to the acute cytotoxic and genotoxic effects of aflatoxin B1 (AFB1), confirming the crucial role of GSTA3 in resistance to AFB1. We now report histopathological changes, tumor formation, biochemical changes and gender response following AFB1 treatment as well as the contribution of oxidative stress. Using a protocol of weekly 0.5 mg AFB1/kg administration, we observed extensive oval (liver stem) cell (OC) proliferation within 1-3 weeks followed by microvesicular lipidosis, megahepatocytes, nuclear inclusions, cholangiomas, and small nodules...
May 23, 2017: Carcinogenesis
https://www.readbyqxmd.com/read/28522175/pharmacological-inhibition-of-soluble-epoxide-hydrolase-or-genetic-deletion-reduces-diclofenac-induced-gastric-ulcers
#12
Sumanta Kumar Goswami, Amelia Ann Rand, Debin Wan, Jun Yang, Bora Inceoglu, Melany Thomas, Christophe Morisseau, Guang-Yu Yang, Bruce D Hammock
AIMS: This research was conducted to evaluate the hypothesis that gastric ulcers caused by the NSAID diclofenac sodium (DCF) can be prevented by the soluble epoxide hydrolase inhibitor TPPU. MAIN METHODS: Mice were administered a single dose of 10, 30 or 100mg/kg of DCF. Once an ulcerative dose of DCF was chosen, mice were pretreated with TPPU for 7days at 0.1mg/kg to evaluate anti-ulcer effects of the sEH inhibitor on anatomy, histopathology, pH, inflammatory markers and epithelial apoptosis of stomachs...
July 1, 2017: Life Sciences
https://www.readbyqxmd.com/read/28521794/in-vitro-synthesis-of-9-10-dihydroxyhexadecanoic-acid-using-recombinant-escherichia-coli
#13
Anees Kaprakkaden, Preeti Srivastava, Virendra Swarup Bisaria
BACKGROUND: Hydroxy fatty acids are widely used in food, chemical and cosmetic industries. A variety of dihydroxy fatty acids have been synthesized so far; however, no studies have been done on the synthesis of 9,10-dihydroxyhexadecanoic acid. In the present study recombinant E. coli has been used for the heterologous expression of fatty acid hydroxylating enzymes and the whole cell lysate of the induced culture was used for in vitro production of 9,10-dihydroxyhexadecanoic acid. RESULTS: A first of its kind proof of principle has been successfully demonstrated for the production of 9,10-dihydroxyhexadecanoic acid using three different enzymes viz...
May 18, 2017: Microbial Cell Factories
https://www.readbyqxmd.com/read/28502798/structure-of-a-soluble-epoxide-hydrolase-identified-in-trichoderma-reesei
#14
Carolina Wilson, Gabriel S De Oliveira, Patrícia P Adriani, Felipe S Chambergo, Marcio V B Dias
Epoxide hydrolases (EHs) are enzymes that have high biotechnological interest for the fine and transformation industry. Several of these enzymes have enantioselectivity, which allows their application in the separation of enantiomeric mixtures of epoxide substrates. Although two different families of EHs have been described, those that have the α/β-hidrolase fold are the most explored for biotechnological purpose. These enzymes are functionally very well studied, but only few members have three-dimensional structures characterised...
August 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28501602/soluble-epoxide-hydrolase-inhibitory-activity-of-components-from-leonurus-japonicus
#15
Hyun Hee Leem, Ga Young Lee, Ji Sun Lee, Hanna Lee, Jang Hoon Kim, Young Ho Kim
One new compound, 10-methoxy-leonurine (1), and four known compounds (2-5) were purified by silica gel, C-18, and Sephadex LH-20 column chromatography from Leonurus japonicus. Their structures were elucidated using one-dimensional (1D)/two-dimensional (2D)-nuclear magnetic resonance (NMR), high-resolution (HR)-electrospray ionization (ESI) mass spectrometry (MS). The compounds were evaluated to determine their inhibition of the catalysis of soluble epoxide hydrolase (sEH). According to the results from in vitro analyses, compounds 1 and 2, which contain guanidine and flavonoid (3), were determined to be potential inhibitors of this enzyme...
May 10, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28497532/arabidopsis-thaliana-epoxide-hydrolase1-ateh1-is-a-cytosolic-epoxide-hydrolase-involved-in-the-synthesis-of-poly-hydroxylated-cutin-monomers
#16
Emmanuelle Pineau, Lin Xu, Hugues Renault, Adrien Trolet, Nicolas Navrot, Pascaline Ullmann, Bertrand Légeret, Gaëtan Verdier, Fred Beisson, Franck Pinot
Epoxide hydrolases (EHs) are present in all living organisms. They have been extensively characterized in mammals; however, their biological functions in plants have not been demonstrated. Based on in silico analysis, we identified AtEH1 (At3g05600), a putative Arabidopsis thaliana epoxide hydrolase possibly involved in cutin monomer synthesis. We expressed AtEH1 in yeast and studied its localization in vivo. We also analyzed the composition of cutin from A. thaliana lines in which this gene was knocked out...
May 12, 2017: New Phytologist
https://www.readbyqxmd.com/read/28492351/mest-a-unique-epoxide-hydrolase-is-essential-for-optimal-growth-of-mycobacterium-tuberculosis-in-the-presence-of-styrene-oxide
#17
Manisha Chownk, Aashish Sharma, Kashmir Singh, Jagdeep Kaur
AIM: mesT of Mycobacterium tuberculosis, a hypothetical/putative epoxide hydrolase, is predicted to convert toxic epoxides to the more water-soluble and less toxic diols. Detailed characterization of the protein was carried out. RESULTS: mesT demonstrated esterase as well as epoxide hydrolase activity. It was membrane bound and was upregulated under hypoxic conditions. The enzyme was able to degrade styrene oxide. The presence of antisense against this gene resulted in the inhibition of in vitro bacterial growth/survival in the presence of styrene oxide...
May 2017: Future Microbiology
https://www.readbyqxmd.com/read/28488585/eets-reduces-lps-induced-hyperpermeability-by-targeting-grp78-mediated-src-activation-and-subsequent-rho-rock-signaling-pathway
#18
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/28485854/podocyte-specific-soluble-epoxide-hydrolase-deficiency-in-mice-attenuates-acute-kidney-injury
#19
Ahmed Bettaieb, Shinichiro Koike, Samah Chahed, Yi Zhao, Santana Bachaalany, Nader Hashoush, James Graham, Fatima Huma, Peter J Havel, Artiom Gruzdev, Darryl C Zeldin, Bruce D Hammock, Fawaz G Haj
Podocytes play an important role in maintaining glomerular function, and podocyte injury is a significant component in the pathogenesis of proteinuria. Soluble epoxide hydrolase (sEH) is a cytosolic enzyme whose genetic deficiency and pharmacological inhibition have beneficial effects on renal function, but its role in podocytes remains unexplored. The objective of this study was to investigate the contribution of sEH in podocytes to lipopolysaccharide (LPS)-induced kidney injury. We report increased sEH transcript and protein expression in murine podocytes upon LPS challenge...
May 9, 2017: FEBS Journal
https://www.readbyqxmd.com/read/28473204/inhibition-of-soluble-epoxide-hydrolase-reduces-portal-pressure-by-protecting-mesenteric-artery-myogenic-responses-in-cirrhotic-rats
#20
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
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