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Epoxyeicosatrienoic

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https://www.readbyqxmd.com/read/29232926/differential-effects-of-seh-inhibitors-on-the-proliferation-and-migration-of-vascular-smooth-muscle-cells
#1
Hyo Seon Kim, Sang Kyum Kim, Keon Wook Kang
Epoxyeicosatrienoic acid (EET) is a cardioprotective metabolite of arachidonic acid. It is known that soluble epoxide hydrolase (sEH) is involved in the metabolic degradation of EET. The abnormal proliferation and migration of vascular smooth muscle cells (VSMCs) play important roles in the pathogenesis of atherosclerosis and restenosis. Thus, the present study investigated the effects of the sEH inhibitor 12-(((tricyclo(3.3.1.13,7)dec-1-ylamino)carbonyl)amino)-dodecanoic acid (AUDA) on platelet-derived growth factor (PDGF)-induced proliferation and migration in rat VSMCs...
December 11, 2017: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/29200270/arachidonic-acid-metabolism-by-human-cardiovascular-cyp2j2-is-modulated-by-doxorubicin
#2
William R Arnold, Javier L Baylon, Emad Tajkhorshid, Aditi Das
Doxorubicin (DOX) is a chemotherapeutic that is used in the treatment of a wide variety of cancers. However, it causes cardiotoxicity partly due to the formation of reactive oxygen species (ROS). CYP2J2 is a human cytochrome P450 that is highly expressed in cardiomyocytes. It converts arachidonic acid (AA) into four different regioisomers of epoxyeicosatrienoic acids (EETs). Using kinetic analyses we show that AA metabolism by CYP2J2 is modulated by DOX. We show that cytochrome P450 reductase (CPR), the redox partner of CYP2J2, metabolizes DOX to 7-deoxydoxorubicin aglycone (7-de-aDOX)...
December 4, 2017: Biochemistry
https://www.readbyqxmd.com/read/29196978/the-role-of-soluble-epoxide-hydrolase-enzyme-on-daunorubicin-mediated-cardiotoxicity
#3
Zaid H Maayah, Ghada Abdelhamid, Osama H Elshenawy, Ahmed A El-Sherbeni, Hassan N Althurwi, Erica McGinn, Doaa Dawood, Ahmad H Alammari, Ayman O S El-Kadi
Several studies have demonstrated the role of cytochrome P450 (CYP) and its associated arachidonic acid (AA) metabolites in the anthracyclines-induced cardiac toxicity. However, the ability of daunorubicin (DNR) to induce cardiotoxicity through the modulation of CYP and its associated AA metabolites has not been investigated yet. Therefore, we hypothesized that DNR-induced cardiotoxicity is mediated through the induction of cardiotoxic hydroxyeicosatetraenoic acids and/or the inhibition of cardioprotctive epoxyeicosatrienoic acids (EETs)...
December 1, 2017: Cardiovascular Toxicology
https://www.readbyqxmd.com/read/29178914/genetic-deletion-or-pharmacological-inhibition-of-soluble-epoxide-hydrolase-reduces-brain-damage-and-attenuates-neuroinflammation-after-intracerebral-hemorrhage
#4
Chun-Hu Wu, Song-Kun Shyue, Tai-Ho Hung, Shin Wen, Chao-Chang Lin, Che-Feng Chang, Szu-Fu Chen
BACKGROUND: Inflammatory responses significantly contribute to neuronal damage and poor functional outcomes following intracerebral hemorrhage (ICH). Soluble epoxide hydrolase (sEH) is known to induce neuroinflammatory responses via degradation of anti-inflammatory epoxyeicosatrienoic acids (EET), and sEH is upregulated in response to brain injury. The present study investigated the involvement of sEH in ICH-induced neuroinflammation, brain damage, and functional deficits using a mouse ICH model and microglial cultures...
November 25, 2017: Journal of Neuroinflammation
https://www.readbyqxmd.com/read/29169114/evaluation-of-antiparkinson-activity-of-ptupb-by-measuring-dopamine-and-its-metabolites-in-drosophila-melanogaster-lc-ms-ms-method-development
#5
Navya Lakkappa, Praveen T Krishnamurthy, Karthik Yamjala, Sung Hee Hwang, Bruce D Hammock, B Babu
Soluble epoxide hydrolase (sEH) inhibition is reported to elevate endogenous epoxyeicosatrienoic acids (EET's), which are known to play an important role in neuroprotection by inhibiting oxidative stress and neuroinflammation. In the present study, PTUPB, a dual inhibitor of sEH and COX-2, has been tested for its antiparkinson activity against rotenone (ROT) induced neurodegeneration in Drosophila model of Parkinson's disease (PD). To determine the efficacy and brain bioavailability of PTUPB a simple, rapid and sensitive LC-MS/MS method was developed and validated for the estimation of PTUPB (Method-I), dopamine (DA) and its metabolites (Method-II) in fly head...
November 16, 2017: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/29158357/evidence-for-a-role-of-vascular-endothelium-in-the-control-of-arterial-wall-viscosity-in-humans
#6
Frederic Roca, Michele Iacob, Isabelle Remy-Jouet, Jeremy Bellien, Robinson Joannides
Arterial wall viscosity (AWV) is a major cause of energy dissipation along the arterial tree. Its determinants remain controversial but an active endothelial regulation has been suggested. Our objective was to assess in humans the physiological role of endothelium-derived nitric oxide (NO), epoxyeicosatrienoic acids and the effect of modulating smooth muscle tone in the regulation of AWV. We simultaneously measured radial artery diameter, wall thickness, and arterial pressure in healthy volunteers during the local infusion of inhibitors of NO-synthase (N(G)-monomethyl-l-arginine), epoxyeicosatrienoic acids synthesis by cytochrome P450 (fluconazole), the epoxyeicosatrienoic acids cellular targets calcium-activated potassium channels (tetraethylammonium), alone and in combination...
November 20, 2017: Hypertension
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
#7
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/29152668/the-role-of-astrocytic-calcium-and-trpv4-channels-in-neurovascular-coupling
#8
Allanah Kenny, Michael J Plank, Tim David
Neuronal activity evokes a localised change in cerebral blood flow in a response known as neurovascular coupling (NVC). Although NVC has been widely studied the exact mechanisms that mediate this response remain unclear; in particular the role of astrocytic calcium is controversial. Mathematical modelling can be a useful tool for investigating the contribution of various signalling pathways towards NVC and for analysing the underlying cellular mechanisms. The lumped parameter model of a neurovascular unit with both potassium and nitric oxide (NO) signalling pathways and comprised of neurons, astrocytes, and vascular cells has been extended to include the glutamate induced astrocytic calcium pathway with epoxyeicosatrienoic acid (EET) signalling and the stretch dependent TRPV4 calcium channel on the astrocytic endfoot...
November 20, 2017: Journal of Computational Neuroscience
https://www.readbyqxmd.com/read/29140411/effect-of-angiotensin-ii-and-acth-on-adrenal-blood-flow-in-the-male-rat-adrenal-gland-in-vivo
#9
Abdul J Shah, Tamas Kriska, Kathryn M Gauthier, John R Falck, William B Campbell
Angiotensin II (Ang II) and adrenocorticotropic hormone (ACTH) regulate adrenal vascular tone in vitro through endothelial and/or zona glomeulosa cell-derived mediators. The role of these mediators in regulating adrenal blood flow (ABF) and mean arterial pressure (MAP) was examined in anesthetized rats. Ang II (0.01-100 ng/kg) increased ABF (maximal increase of 97.2 ± 6.9 perfusion units (PU) at 100 ng/kg) and MAP (basal, 115 ± 7 mm Hg; Ang II, 163 ± 5 mm Hg). ACTH (0.1-1000 ng/kg) also increased ABF (maximum increase of 91...
November 13, 2017: Endocrinology
https://www.readbyqxmd.com/read/29138698/soluble-epoxide-hydrolase-inhibitor-and-14-15-epoxyeicosatrienoic-acid-facilitated-long-term-potentiation-through-camp-and-camkii-in-the-hippocampus
#10
Han-Fang Wu, Yi-Ju Chen, Su-Zhen Wu, Chi-Wei Lee, I-Tuan Chen, Yi-Chao Lee, Chi-Chen Huang, Chung-Hsi Hsing, Chih-Wei Tang, Hui-Ching Lin
Epoxyeicosatrienoic acids (EETs) are derived from arachidonic acid and metabolized by soluble epoxide hydrolase (sEH). The role of EETs in synaptic function in the central nervous system is still largely unknown. We found that pharmacological inhibition of sEH to stabilize endogenous EETs and exogenous 14,15-EET significantly increased the field excitatory postsynaptic potential (fEPSP) response in the CA1 area of the hippocampus, while additionally enhancing high-frequency stimulation- (HFS-) induced long-term potentiation (LTP) and forskolin- (FSK-) induced LTP...
2017: Neural Plasticity
https://www.readbyqxmd.com/read/29109264/epoxide-metabolites-of-arachidonate-and-docosahexaenoate-function-conversely-in-acute-kidney-injury-involved-in-gsk3%C3%AE-signaling
#11
Bing-Qing Deng, Ying Luo, Xin Kang, Chang-Bin Li, Christophe Morisseau, Jun Yang, Kin Sing Stephen Lee, Jian Huang, Da-Yong Hu, Ming-Yu Wu, Ai Peng, Bruce D Hammock, Jun-Yan Liu
Acute kidney injury (AKI) causes severe morbidity and mortality for which new therapeutic strategies are needed. Docosahexaenoic acid (DHA), arachidonic acid (ARA), and their metabolites have various effects in kidney injury, but their molecular mechanisms are largely unknown. Here, we report that 14 (15)-epoxyeicosatrienoic acid [14 (15)-EET] and 19 (20)-epoxydocosapentaenoic acid [19 (20)-EDP], the major epoxide metabolites of ARA and DHA, respectively, have contradictory effects on kidney injury in a murine model of ischemia/reperfusion (I/R)-caused AKI...
November 21, 2017: Proceedings of the National Academy of Sciences of the United States of America
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
#12
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/29055406/the-role-of-soluble-epoxide-hydrolase-in-preeclampsia
#13
Julia M Santos, Jung-A Park, Aby Joiakim, David A Putt, Robert N Taylor, Hyesook Kim
Preeclampsia is a serious complication of pregnancy characterized by the development of vasospasm, hypertension and often associated with proteinuria after the 20th week of gestation. Because termination of pregnancy results in the most efficacious resolution of preeclampsia, it is a leading cause of premature delivery worldwide. In pregnancy, 14,15-epoxyeicosatrienoic acids (EETs) have been shown to facilitate uterine blood flow during preeclampsia, in which the classic vasodilator agents such as nitric oxide and prostacyclin are reduced...
October 2017: Medical Hypotheses
https://www.readbyqxmd.com/read/29050342/role-of-the-cyp3a4-mediated-11-12-epoxyeicosatrienoic-acid-pathway-in-the-development-of-tamoxifen-resistant-breast-cancer
#14
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/29023376/altered-protein-expression-of-cardiac-cyp2j-and-hepatic-cyp2c-cyp4a-and-cyp4f-in-a-mouse-model-of-type-ii-diabetes-a-link-in-the-onset-and-development-of-cardiovascular-disease
#15
Benoit Drolet, Sylvie Pilote, Carolanne Gélinas, Alida-Douce Kamaliza, Audrey Blais-Boilard, Jessica Virgili, Dany Patoine, Chantale Simard
Arachidonic acid can be metabolized by cytochrome P450 (CYP450) enzymes in a tissue- and cell-specific manner to generate vasoactive products such as epoxyeicosatrienoic acids (EETs-cardioprotective) and hydroxyeicosatetraenoic acids (HETEs-cardiotoxic). Type II diabetes is a well-recognized risk factor for developing cardiovascular disease. A mouse model of Type II diabetes (C57BLKS/J-db/db) was used. After sacrifice, livers and hearts were collected, washed, and snap frozen. Total proteins were extracted...
October 12, 2017: Pharmaceutics
https://www.readbyqxmd.com/read/29022765/polymorphisms-in-genes-involved-in-vasoactive-eicosanoid-synthesis-affect-cardiovascular-risk-in-renal-transplant-recipients
#16
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/28989019/drug-disease-interaction-effect-of-inflammation-and-nonsteroidal-anti-inflammatory-drugs-on-cytochrome-p450-metabolites-of-arachidonic-acid
#17
Ali Aghazadeh-Habashi, Waheed Asghar, Fakhreddin Jamali
Inflammatory conditions increase cardiovascular (CV) risk. Some nonsteroidal anti-inflammatory drugs (NSAIDs) that are used to treat pain and inflammation are also associated with CV complications. Inflammation, but not NSAIDs, disrupts the balance of vasodilator and vasoconstrictor components of the renin-angiotensin system within the heart. Herein, we report the effect of both inflammation and NSAIDs (rofecoxib, celecoxib, and meloxicam) on the physiologically active cytochrome P450 metabolites of arachidonic acid (ArA) in the rat with adjuvant arthritis...
October 6, 2017: Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/28975360/beyond-detoxification-a-role-for-mouse-meh-in-the-hepatic-metabolism-of-endogenous-lipids
#18
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/28958841/effects-of-dronedarone-amiodarone-and-their-active-metabolites-on-sequential-metabolism-of-arachidonic-acid-to-epoxyeicosatrienoic-and-dihydroxyeicosatrienoic-acids
#19
Aneesh Karkhanis, Nhan Dai Thien Tram, Eric Chun Yong Chan
Cardiac enzymes such as cytochrome P450 2J2 (CYP2J2) metabolize arachidonic acid (AA) to cardioprotective epoxyeicosatrienoic acids (EETs), which in turn are metabolized by soluble epoxide hydrolase (sEH) to dihydroxyeicosatrienoic acids (DHETs). As EETs and less potent DHETs exhibit cardioprotective and vasoprotective functions, optimum levels of cardiac EETs are paramount in cardiac homeostasis. Previously, we demonstrated that dronedarone, amiodarone and their main metabolites, namely N-desbutyldronedarone (NDBD) and N-desethylamiodarone (NDEA), potently inhibit human cardiac CYP2J2-mediated astemizole metabolism in vitro...
September 25, 2017: Biochemical Pharmacology
https://www.readbyqxmd.com/read/28937442/orally-active-epoxyeicosatrienoic-acid-analogs
#20
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
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