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https://www.readbyqxmd.com/read/29236467/recent-advances-in-enzymatic-complexity-generation-cyclization-reactions
#1
Christopher T Walsh, Yi Tang
Enzymes in biosynthetic pathways, especially in plant and microbial metabolism, generate structural and functional group complexity in small molecules by conversion of acyclic frameworks to cyclic scaffolds in short, efficient routes. The distinct chemical logic used by several distinct classes of cyclases, oxidative and non-oxidative, has recently been elucidated by genome mining, heterologous expression, and genetic and mechanistic analyses. These include enzymes carrying out pericyclic transformations, pyran synthases, tandem acting epoxygenases and epoxide "hydrolases", as well as oxygenases and radical SAM enzymes that involve rearrangements of substrate radicals under aerobic or anaerobic conditions, respectively...
December 13, 2017: Biochemistry
https://www.readbyqxmd.com/read/29158256/heart-failure-induced-activation-of-phospholipase-ipla2%C3%AE-%C3%A2-generates-hydroxyeicosatetraenoic-acids-opening-the-mitochondrial-permeability-transition-pore
#2
Sung Ho Moon, Xinping Liu, Ari M Cedars, Kui Yang, Michael A Kiebish, Susan M Joseph, John Kelley, Christopher M Jenkins, Richard W Gross
Congestive heart failure typically arises from cardiac myocyte necrosis/apoptosis, associated with the pathological opening of the mitochondrial permeability transition pore (mPTP). mPTP opening decreases the mitochondrial membrane potential leading to the activation of Ca(2+)-independent phospholipase A2γ (iPLA2γ) and the production of downstream toxic metabolites. However, the array of enzymatic mediators and the exact chemical mechanisms responsible for modulating myocardial mPTP opening remain unclear...
November 20, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/29081082/epoxyeicosatrienoic-acid-inhibits-the-apoptosis-of-cerebral-microvascular-smooth-muscle-cells-by-oxygen-glucose-deprivation-via-targeting-the-jnk-c-jun-and-mtor-signaling-pathways
#3
Youyang Qu, Yu Liu, Yanmei Zhu, Li Chen, Wei Sun, Yulan Zhu
As a component of the neurovascular unit, cerebral smooth muscle cells (CSMCs) are an important mediator in the development of cerebral vascular diseases such as stroke. Epoxyeicosatrienoic acids (EETs) are the products of arachidonic acid catalyzed by cytochrome P450 epoxygenase. EETs are shown to exert neuroprotective effects. In this article, the role of EET in the growth and apoptosis of CSMCs and the underlying mechanisms under oxygen glucose deprivation (OGD) conditions were addressed. The viability of CMSCs was decreased significantly in the OGD group, while different subtypes of EETs, especially 14,15-EET, could increase the viability of CSMCs under OGD conditions...
October 27, 2017: Molecules and Cells
https://www.readbyqxmd.com/read/29080699/therapeutic-potential-of-omega-3-fatty-acid-derived-epoxyeicosanoids-in-cardiovascular-and-inflammatory-diseases
#4
REVIEW
Wolf-Hagen Schunck, Anne Konkel, Robert Fischer, Karsten-Henrich Weylandt
Numerous benefits have been attributed to dietary long-chain omega-3 polyunsaturated fatty acids (n-3 LC-PUFAs), including protection against cardiac arrhythmia, triglyceride-lowering, amelioration of inflammatory, and neurodegenerative disorders. This review covers recent findings indicating that a variety of these beneficial effects are mediated by "omega-3 epoxyeicosanoids", a class of novel n-3 LC-PUFA-derived lipid mediators, which are generated via the cytochrome P450 (CYP) epoxygenase pathway. CYP enzymes, previously identified as arachidonic acid (20:4n-6; AA) epoxygenases, accept eicosapentaenoic acid (20:5n-3; EPA) and docosahexaenoic acid (22:6n-3; DHA), the major fish oil n-3 LC-PUFAs, as efficient alternative substrates...
November 7, 2017: Pharmacology & Therapeutics
https://www.readbyqxmd.com/read/29071994/-effect-of-jiaji-ex-b-2-electroacupuncture-preconditioning-on-expression-of-cytochrome-p-450-signaling-pathways-in-myocardial-ischemia-reperfusion-rats
#5
Yang Li, Ming-Lu Shao, Hui-Juan Yu, Qi-Wen Tan, Hua-Feng Cui
OBJECTIVE: To investigate the effect of "Jiaji"(EX-B 2)-electroacupuncture(EA) preconditioning on the myocardium and expression of cytochrome P 450 signaling pathways of myocardial cells in myocardial ischemia-reperfusion injury(MI/RI) rats. METHODS: Sixty male Wistar rats were randomly divided into sham operation, model, Jiaji, Neiguan(PC 6), Yanglingquan(GB 34) and Quchi(LI 11) groups (n=10 in each group). MI/RI model was established by occlusion of the descen-ding anterior branch of the left coronary artery...
February 25, 2017: Zhen Ci Yan Jiu, Acupuncture Research
https://www.readbyqxmd.com/read/29050342/role-of-the-cyp3a4-mediated-11-12-epoxyeicosatrienoic-acid-pathway-in-the-development-of-tamoxifen-resistant-breast-cancer
#6
Nguyen Thi Thuy Phuong, Ji Won Kim, Jung-Ae Kim, Jang Su Jeon, Ji-Yoon Lee, Wen Jun Xu, Jin Won Yang, Sang Kyum Kim, Keon Wook Kang
Epoxyeicosatrienoic acid (EET) production via cytochrome P450 (CYP) epoxygenases closely correlates with the progression of breast cancer. However, its role in the development of chemoresistant breast cancers has yet to be elucidated. Here, we found that CYP3A4 expression and its epoxy-product, 11,12-epoxyeicosatrienoic acid (11,12-EET) was enhanced in tamoxifen (TAM)-resistant MCF-7 (TAMR-MCF-7) breast cancer cells compared to control MCF-7 cells. Treatment of TAMR-MCF-7 cells with ketoconazole and azamulin (selective CYP3A4 inhibitors) or 14,15-epoxyeicosa-5(Z)-enoic acid (14,15-EEZE, an EET antagonist) inhibited cellular proliferation and recovered the sensitivity to 4-hydroxytamoxifen...
September 19, 2017: Oncotarget
https://www.readbyqxmd.com/read/29022765/polymorphisms-in-genes-involved-in-vasoactive-eicosanoid-synthesis-affect-cardiovascular-risk-in-renal-transplant-recipients
#7
Guillermo Gervasini, Enrique Luna, Guadalupe Garcia-Pino, Lilia Azevedo, Sonia Mota-Zamorano, Juan José Cubero
OBJECTIVE: Arachidonic acid metabolism by cytochrome P450 (CYP) epoxygenases leads to epoxyeicosatrienoic acids (EETs), which are eicosanoids with vasodilator and anti-inflammatory properties. We aim to determine whether genetic variability in these routes may contribute to cardiovascular (CV) risk in renal transplant recipients. METHODS: In a cohort of 355 patients, we determined the presence of two polymorphisms, CYP2C8*3 and CYP2J2*7, known to affect eicosanoid levels...
November 8, 2017: Current Medical Research and Opinion
https://www.readbyqxmd.com/read/28975360/beyond-detoxification-a-role-for-mouse-meh-in-the-hepatic-metabolism-of-endogenous-lipids
#8
Anne Marowsky, Imke Meyer, Kira Erismann-Ebner, Giovanni Pellegrini, Nandkishor Mule, Michael Arand
Microsomal and soluble epoxide hydrolase (mEH and sEH) fulfill apparently distinct roles: Whereas mEH detoxifies xenobiotics, sEH hydrolyzes fatty acid (FA) signaling molecules and is thus implicated in a variety of physiological functions. These epoxy FAs comprise epoxyeicosatrienoic acids (EETs) and epoxy-octadecenoic acids (EpOMEs), which are formed by CYP epoxygenases from arachidonic acid (AA) and linoleic acid, respectively, and then are hydrolyzed to their respective diols, the so-called DHETs and DiHOMEs...
October 3, 2017: Archives of Toxicology
https://www.readbyqxmd.com/read/28937442/orally-active-epoxyeicosatrienoic-acid-analogs
#9
William B Campbell, John D Imig, James M Schmitz, John R Falck
Biologically active epoxyeicosatrienoic acid (EET) regioisomers are synthesized from arachidonic acid by cytochrome P450 epoxygenases of endothelial, myocardial, and renal tubular cells. EETs relax vascular smooth muscle and decrease inflammatory cell adhesion and cytokine release. Renal EETs promote sodium excretion and vasodilation to decrease hypertension. Cardiac EETs reduce infarct size after ischemia-reperfusion injury and decrease fibrosis and inflammation in heart failure. In diabetes, EETs improve insulin sensitivity, increase glucose tolerance, and reduce the renal injury...
October 2017: Journal of Cardiovascular Pharmacology
https://www.readbyqxmd.com/read/28919040/heme-binding-biguanides-target-cytochrome-p450-dependent-cancer-cell-mitochondria
#10
Zhijun Guo, Irina F Sevrioukova, Ilia G Denisov, Xia Zhang, Ting-Lan Chiu, Dafydd G Thomas, Eric A Hanse, Rebecca A D Cuellar, Yelena V Grinkova, Vanessa Wankhede Langenfeld, Daniel S Swedien, Justin D Stamschror, Juan Alvarez, Fernando Luna, Adela Galván, Young Kyung Bae, Julia D Wulfkuhle, Rosa I Gallagher, Emanuel F Petricoin, Beverly Norris, Craig M Flory, Robert J Schumacher, M Gerard O'Sullivan, Qing Cao, Haitao Chu, John D Lipscomb, William M Atkins, Kalpna Gupta, Ameeta Kelekar, Ian A Blair, Jorge H Capdevila, John R Falck, Stephen G Sligar, Thomas L Poulos, Gunda I Georg, Elizabeth Ambrose, David A Potter
The mechanisms by which cancer cell-intrinsic CYP monooxygenases promote tumor progression are largely unknown. CYP3A4 was unexpectedly associated with breast cancer mitochondria and synthesized arachidonic acid (AA)-derived epoxyeicosatrienoic acids (EETs), which promoted the electron transport chain/respiration and inhibited AMPKα. CYP3A4 knockdown activated AMPKα, promoted autophagy, and prevented mammary tumor formation. The diabetes drug metformin inhibited CYP3A4-mediated EET biosynthesis and depleted cancer cell-intrinsic EETs...
October 19, 2017: Cell Chemical Biology
https://www.readbyqxmd.com/read/28881620/eets-reduces-lps-induced-hyperpermeability-by-targeting-grp78-mediated-src-activation-and-subsequent-rho-rock-signaling-pathway
#11
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...
August 1, 2017: Oncotarget
https://www.readbyqxmd.com/read/28877879/uninephrectomy-and-apical-fluid-shear-stress-decrease-enac-abundance-in-collecting-duct-principal-cells
#12
Thomas Ernandez, Khalil Udwan, Alexandra Chassot, Pierre-Yves Martin, Eric Feraille
Acute nephron reduction such as after living kidney donation may increase the risk of hypertension. Uninephrectomy induces major hemodynamic changes in the remaining kidney resulting in rapid increase of single nephron GFR and fluid delivery in the distal nephron. Decreased sodium (Na) fractional reabsorption after the distal tubule has been reported after uninephrectomy in animals preserving volume homeostasis. In the present study, we thought to specifically explore the effect of unilateral nephrectomy on ENaC subunits expression in mice...
September 6, 2017: American Journal of Physiology. Renal Physiology
https://www.readbyqxmd.com/read/28842441/carotid-artery-stenosis-in-hypertensive-rats-impairs-dilatory-pathways-in-parenchymal-arterioles
#13
Nusrat Matin, Courtney Fisher, William F Jackson, Janice M Diaz-Otero, Anne M Dorrance
Hypertension is a leading risk factor for vascular cognitive impairment and is strongly associated with carotid artery stenosis. In normotensive rats, chronic cerebral hypoperfusion induced by bilateral common carotid artery stenosis (BCAS) leads to cognitive impairment that is associated with impaired endothelium-dependent dilation in parenchymal arterioles (PAs). The aim of this study was to assess the effects of BCAS on PA function and structure in stroke prone spontaneously hypertensive rats (SHRSP), a model of human essential hypertension...
August 25, 2017: American Journal of Physiology. Heart and Circulatory Physiology
https://www.readbyqxmd.com/read/28826940/distinct-oxylipin-alterations-in-diverse-models-of-cystic-kidney-diseases
#14
Md Monirujjaman, Jessay G Devassy, Tamio Yamaguchi, Nikhil Sidhu, Masanori Kugita, Melissa Gabbs, Shizuko Nagao, Jing Zhou, Amir Ravandi, Harold M Aukema
Cystic kidney diseases are characterized by multiple renal cysts and are the leading cause of inherited renal disease. Oxylipins are bioactive lipids derived from fatty acids formed via cyclooxygenase, lipoxygenase and cytochrome P450 activity, and are important regulators of renal health and disease. Oxylipins are altered in nephronophthisis, a type of cystic kidney disease. To further investigate and to determine whether other cystic renal diseases share these abnormalities, a targeted lipidomic analysis of renal oxylipins was performed in orthologous models of autosomal dominant polycystic kidney disease 1 (Mx1Cre(+)Pkd1(flox/flox) mouse) and 2 (Pkd2(ws25/-) mouse), autosomal recessive polycystic kidney disease (PCK rat) and nephronophthisis (jck/jck mouse)...
December 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28761179/soluble-epoxide-hydrolase-inhibition-protected-against-angiotensin-ii-induced-adventitial-remodeling
#15
Chi Zhou, Jin Huang, Qing Li, Jiali Nie, Xizhen Xu, Dao Wen Wang
Epoxyeicosatrienoic acids (EETs), the metabolites of cytochrome P450 epoxygenases derived from arachidonic acid, exert important biological activities in maintaining cardiovascular homeostasis. Soluble epoxide hydrolase (sEH) hydrolyzes EETs to less biologically active dihydroxyeicosatrienoic acids. However, the effects of sEH inhibition on adventitial remodeling remain inconclusive. In this study, the adventitial remodeling model was established by continuous Ang II infusion for 2 weeks in C57BL/6 J mice, before which sEH inhibitor 1-trifluoromethoxyphenyl-3-(1-propionylpiperidin-4-yl) urea (TPPU) was administered by gavage...
July 31, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28734877/enzymatic-and-free-radical-formation-of-cis-and-trans-epoxyeicosatrienoic-acids-in-vitro-and-in-vivo
#16
Theresa Aliwarga, Brianne S Raccor, Rozenn N Lemaitre, Nona Sotoodehnia, Sina A Gharib, Libin Xu, Rheem A Totah
Epoxyeicosatrienoic acids (EETs) are metabolites of arachidonic acid (AA) oxidation that have important cardioprotective and signaling properties. AA is an ω-6 polyunsaturated fatty acid (PUFA) that is prone to autoxidation. Although hydroperoxides and isoprostanes are major autoxidation products of AA, EETs are also formed from the largely overlooked peroxyl radical addition mechanism. While autoxidation yields both cis- and trans-EETs, cytochrome P450 (CYP) epoxygenases have been shown to exclusively catalyze the formation of all regioisomer cis-EETs, on each of the double bonds...
November 2017: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/28713881/drug-delivery-and-nanoformulations-for-the-cardiovascular-system
#17
W J Geldenhuys, M T Khayat, J Yun, M A Nayeem
Therapeutic delivery to the cardiovascular system may play an important role in the successful treatment of a variety of disease state, including atherosclerosis, ischemic-reperfusion injury and other types of microvascular diseases including hypertension. In this review we evaluate the different options available for the development of suitable delivery systems that include the delivery of small organic compounds [adenosin A2A receptor agonist (CGS 21680), CYP-epoxygenases inhibitor (N-(methylsulfonyl)-2-(2-propynyloxy)-benzenehexanamide, trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy] benzoic acid), soluble epoxide hydrolase inhibitor (N-methylsulfonyl-12,12-dibromododec-11-enamide), PPARγ agonist (rosiglitazone) and PPARγ antagonist (T0070907)], nanoparticles, peptides, and siRNA to the cardiovascular system...
February 2017: Research & Reviews. Drug Delivery
https://www.readbyqxmd.com/read/28713267/epoxyeicosatrienoic-acid-analog-decreases-renal-fibrosis-by-reducing-epithelial-to-mesenchymal-transition
#18
Melissa Skibba, Md Abdul Hye Khan, Lauren L Kolb, Michael M Yeboah, John R Falck, Radhika Amaradhi, John D Imig
Renal fibrosis, which is a critical pathophysiological event in chronic kidney diseases, is associated with renal epithelial-to-mesenchymal transition (EMT). Epoxyeicosatrienoic acids (EETs) are Cyp epoxygenase arachidonic acid metabolites that demonstrate biological actions that result in kidney protection. Herein, we investigated the ability of 14,15-EET and its synthetic analog, EET-A, to reduce kidney fibrosis induced by unilateral ureter obstruction (UUO). C57/BL6 male mice underwent sham or UUO surgical procedures and were treated with 14,15-EET or EET-A in osmotic pump (i...
2017: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/28687674/anti-inflammatory-%C3%AF-3-endocannabinoid-epoxides
#19
Daniel R McDougle, Josephine E Watson, Amr A Abdeen, Reheman Adili, Megan P Caputo, John E Krapf, Rodney W Johnson, Kristopher A Kilian, Michael Holinstat, Aditi Das
Clinical studies suggest that diets rich in ω-3 polyunsaturated fatty acids (PUFAs) provide beneficial anti-inflammatory effects, in part through their conversion to bioactive metabolites. Here we report on the endogenous production of a previously unknown class of ω-3 PUFA-derived lipid metabolites that originate from the crosstalk between endocannabinoid and cytochrome P450 (CYP) epoxygenase metabolic pathways. The ω-3 endocannabinoid epoxides are derived from docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) to form epoxyeicosatetraenoic acid-ethanolamide (EEQ-EA) and epoxydocosapentaenoic acid-ethanolamide (EDP-EA), respectively...
July 25, 2017: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/28616567/cyp2c19-variants-and-epoxyeicosatrienoic-acids-in-patients-with-microvascular-angina
#20
Tomonori Akasaka, Daisuke Sueta, Yuichiro Arima, Noriaki Tabata, Seiji Takashio, Yasuhiro Izumiya, Eiichiro Yamamoto, Kenichi Tsujita, Sunao Kojima, Koichi Kaikita, Ayami Kajiwara, Kazunori Morita, Kentaro Oniki, Junji Saruwatari, Kazuko Nakagawa, Seiji Hokimoto
BACKGROUND: Categorization as a cytochrome P450 (CYP) 2C19 poor metabolizer (PM) is reported to be an independent risk factor for cardiovascular disease. Epoxyeicosatrienoic acids (EETs) are metabolites of arachidonic acid by CYP2C19 epoxygenases and anti-inflammatory properties, especially in microvascular tissues. We examined the impact of CYP2C19 polymorphisms and EETs on the patients with microvascular angina (MVA) caused by coronary microvascular dysfunction. METHODS AND RESULTS: We examined CYP2C19 genotypes in patients with MVA (n = 81)...
June 2017: IJC Heart & Vasculature
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