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Epoxide hydrolase

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https://www.readbyqxmd.com/read/28298080/unraveling-energy-and-dynamics-determinants-to-interpret-protein-functional-plasticity-the-limonene-1-2-epoxide-hydrolases-case-study
#1
Silvia Rinaldi, Alessandro Gori, Celeste Annovazzi, Erica Elisa Ferrandi, Daniela Monti, Giorgio Colombo
The balance between structural stability and functional plasticity in proteins that share common three-dimensional folds is the key factor that drives protein evolvability. The ability to distinguish the parts of homologous proteins that underlie common structural organization patterns from the parts acting as regulatory modules that can sustain modifications in response to evolutionary pressure may provide fundamental insights for understanding sequence-structure-dynamics relationships. In applicative terms, this would help develop rational protein design methods...
March 15, 2017: Journal of Chemical Information and Modeling
https://www.readbyqxmd.com/read/28296232/inhibitors-of-soluble-epoxide-hydrolase-minimize-ischemia-reperfusion-induced-cardiac-damage-in-normal-hypertensive-and-diabetic-rats
#2
Oliul Islam, Prashanth Patil, Sumanta K Goswami, Rema Razdan, Mohammed N Inamdar, Mohammed Rizwan, Jubin Mathew, Bora Inceoglu, Kin S Stephen Lee, Sung H Hwang, Bruce D Hammock
AIM: We designed a study to evaluate the cardioprotective effect of two soluble epoxide hydrolase (sEH) inhibitors, 1-(1-propanoylpiperidin-4-yl)-3-(4-trifluoromethoxy)phenyl)urea (TPPU) and trans-4-{4-[3-(4-trifluoromethoxyphenyl)-ureido]cyclohexyloxy}benzoic acid (t-TUCB), in ischemia-reperfusion (IR) model. METHODS: Cardioprotective effects of the sEH inhibitors were evaluated against IR-induced myocardial damage in hearts from normal, hypertensive and diabetic rats using Langendorff's apparatus...
March 15, 2017: Cardiovascular Therapeutics
https://www.readbyqxmd.com/read/28295428/atheroprotective-effects-and-molecular-targets-of-tanshinones-derived-from-herbal-medicine-danshen
#3
REVIEW
Jian Fang, Peter J Little, Suowen Xu
Medicinal plant-derived bioactive compounds modulate multiple therapeutic targets in cardiovascular diseases (CVDs), rendering herb-derived phytochemicals effective against one of the major CVDs-atherosclerosis. Danshen (Salvia milthiorriza Bunge) is a Chinese medicine that has been used in cardio- and cerebro-vascular therapeutic remedies in Asian countries for many years. Emerging evidence from cellular, animal, and clinical studies suggests that major lipophilic tanshinones from Danshen can treat atherosclerotic CVDs...
February 16, 2017: Medicinal Research Reviews
https://www.readbyqxmd.com/read/28293507/soluble-epoxide-hydrolase-inhibition-and-epoxyeicosatrienoic-acid-treatment-improve-vascularization-of-engineered-skin-substitutes
#4
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/28291596/isolation-and-characterization-of-9-lipoxygenase-and-epoxide-hydrolase-2-genes-insight-into-lactone-biosynthesis-in-mango-fruit-mangifera-indica-l
#5
Ashish B Deshpande, Hemangi G Chidley, Pranjali S Oak, Keshav H Pujari, Ashok P Giri, Vidya S Gupta
Uniqueness and diversity of mango flavour across various cultivars are well known. Among various flavour metabolites lactones form an important class of aroma volatiles in certain mango varieties due to their ripening specific appearance and lower odour detection threshold. In spite of their biological and biochemical importance, lactone biosynthetic pathway in plants remains elusive. Present study encompasses quantitative real-time analysis of 9-lipoxygenase (Mi9LOX), epoxide hydrolase 2 (MiEH2), peroxygenase, hydroperoxide lyase and acyl-CoA-oxidase genes during various developmental and ripening stages in fruit of Alphonso, Pairi and Kent cultivars with high, low and no lactone content and explains their variable lactone content...
March 10, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28281333/discovering-drugs-with-dna-encoded-library-technology-from-concept-to-clinic-with-an-inhibitor-of-soluble-epoxide-hydrolase
#6
Svetlana Belyanskaya, Yun Ding, James Callahan, Aili Lazaar, David Israel
DNA encoded chemical library technology was developed with the vision of becoming a transformational platform for drug discovery. The hope was that a new screening paradigm for low molecular weight drugs would be enabled by combining the vast molecular diversity achievable with combinatorial chemistry, the information encoding attributes of DNA, the power of molecular biology and a streamlined selection-based discovery process. We describe the discovery and early clinical development of GSK2256294, an inhibitor of the enzyme soluble epoxide hydrolase (sEH, EPHX2) using Encoded Library Technology (ELT)...
March 9, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28279529/soluble-epoxide-hydrolase-inhibitors-of-indolinone-alkaloids-and-phenolic-derivatives-from-cimicifuga-dahurica-turcz-maxim
#7
Nguyen Phuong Thao, Bui Thi Thuy Luyen, Ji Sun Lee, Jang Hoon Kim, Young Ho Kim
The aim of this study was to search for potential therapeutic agents by identifying novel inhibitors of soluble epoxide hydrolase (sEH) from natural plants using an in silico approach. We found that an ethanolic extract from the roots of Cimicifuga dahurica (Turcz.) Maxim. significantly inhibited sEH in vitro. In a phytochemical investigation using assay-guided fractionation of the dichloromethane extract of C. dahurica, we isolated two new indolinone alkaloids (5 and 6) and five related constituents (1-4, and 7) and established their structures based on an extensive analysis using 1D and 2D NMR, and MS methods...
February 9, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28271340/an-overview-on-the-enhancement-of-enantioselectivity-and-stability-of-microbial-epoxide-hydrolases
#8
REVIEW
Priya Saini, Dipti Sareen
Epoxide hydrolases (EHs; 3.3.2.x) catalyze the enantioselective ring opening of racemic epoxides to the corresponding enantiopure vicinal diols and remaining equivalent unreacted epoxides. These epoxides and diols are used for the synthesis of chiral drug intermediates. With an upsurge in the methods for identification of novel microbial EHs, a lot of EHs have been discovered and utilized for kinetic resolution of racemic epoxides. However, there is still a constraint on the account of limited EHs being successfully applied on the preparative scale for industrial biotransformations...
March 2017: Molecular Biotechnology
https://www.readbyqxmd.com/read/28270581/reply-to-misclassification-of-pfeh1-and-pfeh2-as-epoxide-hydrolases
#9
Daniel E Goldberg, Natalie J Spillman
No abstract text is available yet for this article.
March 7, 2017: MBio
https://www.readbyqxmd.com/read/28259677/soluble-epoxide-hydrolase-inhibition-alleviates-neuropathy-in-akita-ins2-akita-mice
#10
Karen Wagner, Jennifer Gilda, Jun Yang, Debin Wan, Christophe Morisseau, Aldrin V Gomes, Bruce D Hammock
The soluble epoxide hydrolase (sEH) is a regulatory enzyme responsible for the metabolism of bioactive lipid epoxides of both omega-6 and omega-3 long chain polyunsaturated fatty acids. These natural epoxides mediate cell signaling in several physiological functions including blocking inflammation, high blood pressure and both inflammatory and neuropathic pain. Inhibition of the sEH maintains the level of endogenous bioactive epoxy-fatty acids (EpFA) and allows them to exert their generally beneficial effects...
March 1, 2017: Behavioural Brain Research
https://www.readbyqxmd.com/read/28259037/altered-soluble-epoxide-hydrolase-derived-oxylipins-in-patients-with-seasonal-major-depression-an-exploratory-study
#11
Marie Hennebelle, Yurika Otoki, Jun Yang, Bruce D Hammock, Anthony J Levitt, Ameer Y Taha, Walter Swardfager
Many cytochrome p450-derived lipids promote resolution of inflammation, in contrast to their soluble epoxide hydrolase(sEH)-derived oxylipin breakdown products. Here we compare plasma oxylipins and precursor fatty acids between seasons in participants with major depressive disorder with seasonal pattern (MDD-s). Euthymic participants with a history of MDD-s recruited in summer-fall were followed-up in winter. At both visits, a structured clinical interview (DSM-5 criteria) and the Beck Depression Inventory II (BDI-II) were administered...
February 27, 2017: Psychiatry Research
https://www.readbyqxmd.com/read/28255523/inhibition-of-soluble-epoxide-hydrolase-as-a-novel-approach-to-high-dose-diazepam-induced-hypotension
#12
Arzu Ulu, Bora Inceoglu, Jun Yang, Vikrant Singh, Stephen Vito, Heike Wulff, Bruce D Hammock
CONTEXT: Hypotension is one of the dose limiting side effects of benzodiazepines (BZDs), in particular of diazepam (DZP) which is still widely used in the clinic. Currently, only one FDA approved antidote exists for BZD overdose and novel approaches are needed to improve management of DZP overdose, dependency and withdrawal. OBJECTIVE: Here, we hypothesized that increasing bioactive lipid mediators termed epoxy fatty acids (EpFAs) will prevent hypotension, as was shown previously in a murine model of LPS-induced hypotension...
June 2016: Journal of Clinical 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
#13
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/28199961/proteomic-analysis-of-laser-capture-microdissected-focal-lesions-in-a-rat-model-of-progenitor-marker-positive-hepatocellular-carcinoma
#14
Adeola O Adebayo Michael, Nagib Ahsan, Valerie Zabala, Heather Francois-Vaughan, Stephanie Post, Kate E Brilliant, Arthur R Salomon, Jennifer A Sanders, Philip A Gruppuso
We have shown previously that rapamycin, the canonical inhibitor of the mechanistic target of rapamycin (mTOR) complex 1, markedly inhibits the growth of focal lesions in the resistant hepatocyte (Solt-Farber) model of hepatocellular carcinoma (HCC) in the rat. In the present study, we characterized the proteome of persistent, pre-neoplastic focal lesions in this model. One group was administered rapamycin by subcutaneous pellet for 3 weeks following partial hepatectomy and euthanized 4 weeks after the cessation of rapamycin...
February 9, 2017: Oncotarget
https://www.readbyqxmd.com/read/28188798/in-silico-investigation-of-cycloartane-triterpene-derivatives-from-cimicifuga-dahurica-turcz-maxim-roots-for-the-development-of-potent-soluble-epoxide-hydrolase-inhibitors
#15
Nguyen Phuong Thao, Jang Hoon Kim, Bui Thi Thuy Luyen, Nguyen Tien Dat, Young Ho Kim
In our search for natural soluble epoxide hydrolase (sEH) inhibitors from plants, we found that an ethanolic extract of the roots of Cimicifuga dahurica (Turcz.) Maxim. significantly inhibits sEH in vitro. A phytochemical study on the dichloromethane fraction of C. dahurica resulted in the isolation of two new cycloartane triterpenoids (1 and 6), together with 13 known cycloartane analogues (2-5 and 7-15). The structures of compounds were determined by spectroscopic methods. All of the triterpenoid derivatives inhibited sEH enzymatic activity in a concentration-dependent manner, and 13 of the tested compounds showed significant activity...
February 7, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28185955/endothelial-nox4-based-nadph-oxidase-regulates-atherosclerosis-via-soluble-epoxide-hydrolase
#16
Pingping Hu, Xiaojuan Wu, Alok R Khandelwal, Weimin Yu, Zaicheng Xu, Lili Chen, Jian Yang, Robert M Weisbrod, Kin Sing Stephen Lee, Francesca Seta, Bruce D Hammock, Richard A Cohen, Chunyu Zeng, Xiaoyong Tong
Nox4-based NADPH oxidase is a major reactive oxygen species-generating enzyme in the vasculature, but its role in atherosclerosis remains controversial. OBJECTIVE: Our goal was to investigate the mechanisms of endothelial Nox4 in regulating atherosclerosis. APPROACH AND RESULTS: Atherosclerosis-prone conditions (disturbed blood flow, type I diabetes, and Western diet) downregulated endothelial Nox4 mRNA in arteries. To address whether the downregulated endothelial Nox4 was directly involved in the development of atherosclerosis, we generated mice carrying a human Nox4 P437H dominant negative mutation (Nox4DN), driven by the endothelial specific promoter Tie-2, on atherosclerosis-prone genetic background (ApoE deficient mice) to mimic the effect of decreased endothelial Nox4...
February 6, 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28140329/the-role-of-cytochrome-p450-epoxygenases-soluble-epoxide-hydrolase-and-epoxyeicosatrienoic-acids-in-metabolic-diseases
#17
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/28132911/effect-of-alpha-lipoic-acid-on-leukotriene-a4-hydrolase
#18
María José Torres, Angélica Fierro, C David Pessoa-Mahana, Javier Romero-Parra, Gonzalo Cabrera, Mario Faúndez
Leukotriene A4 hydrolase is a soluble enzyme with epoxide hydrolase and aminopeptidase activities catalysing the conversion of leukotriene A4 to leukotriene B4 and the hydrolysis of the peptide proline-glycine-proline. Imbalances in leukotriene B4 synthesis are related to several pathologic conditions. Currently there are no available drugs capable to modulate the synthesis of leukotriene B4 or to block its receptors. Here we show the inhibitory profile of alpha lipoic acid on the activity of leukotriene A4 Hydrolase...
January 26, 2017: European Journal of Pharmacology
https://www.readbyqxmd.com/read/28120429/structural-insights-into-human-microsomal-epoxide-hydrolase-by-combined-homology-modeling-molecular-dynamics-simulations-and-molecular-docking-calculations
#19
Patricia Saenz-Méndez, Aline Katz, María Lucía Pérez-Kempner, Oscar N Ventura, Marta Vázquez
A new homology model of human microsomal epoxide hydrolase was derived based on multiple templates. The model obtained was fully evaluated, including MD simulations and ensemble-based docking, showing that the quality of the structure is better than that of only previously known model. Particularly, a catalytic triad was clearly identified, in agreement with the experimental information available. Analysis of intermediates in the enzymatic mechanism led to the identification of key residues for substrate binding, stereoselectivity, and intermediate stabilization during the reaction...
January 24, 2017: Proteins
https://www.readbyqxmd.com/read/28115652/candidate-risk-factors-and-mechanisms-for-tolvaptan-induced-liver-injury-are-identified-using-a-collaborative-cross-approach
#20
Merrie Mosedale, Yunjung Kim, William J Brock, Sharin E Roth, Tim Wiltshire, J Scott Eaddy, Gregory R Keele, Robert W Corty, Yuying Xie, William Valdar, Paul B Watkins
Clinical trials of tolvaptan showed it to be a promising candidate for the treatment of Autosomal Dominant Polycystic Kidney Disease (ADPKD) but also revealed potential for idiosyncratic drug-induced liver injury (DILI) in this patient population. To identify risk factors and mechanisms underlying tolvaptan DILI, 8 mice in each of 45 strains of the genetically diverse Collaborative Cross (CC) mouse population were treated with a single oral dose of either tolvaptan or vehicle. Significant elevations in plasma alanine aminotransferase (ALT) were observed in tolvaptan-treated animals in 3 of the 45 strains...
January 23, 2017: Toxicological Sciences: An Official Journal of the Society of Toxicology
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