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1783-84-2

1783-84-2 | 8,11,14-Eicosatrienoic acid, (8Z,11Z,14Z)-

CAS No: 1783-84-2 Catalog No: AG0025WS MDL No:MFCD00065721

Product Description

Catalog Number:
AG0025WS
Chemical Name:
8,11,14-Eicosatrienoic acid, (8Z,11Z,14Z)-
CAS Number:
1783-84-2
Molecular Formula:
C20H34O2
Molecular Weight:
306.4828
MDL Number:
MFCD00065721
IUPAC Name:
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
InChI:
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
InChI Key:
HOBAELRKJCKHQD-QNEBEIHSSA-N
SMILES:
CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
EC Number:
217-233-0
UNII:
FC398RK06S

Properties

Complexity:
327  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
3  
Exact Mass:
306.256g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
306.49g/mol
Monoisotopic Mass:
306.256g/mol
Rotatable Bond Count:
15  
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.2  

Literature

Title Journal
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Vascular hepoxilin and trioxilins mediate vasorelaxation through TP receptor inhibition in mouse arteries. Acta physiologica (Oxford, England) 20170101
Beyond detoxification: a role for mouse mEH in the hepatic metabolism of endogenous lipids. Archives of toxicology 20170101
Epoxyeicosatrienoic acid analog attenuates the development of malignant hypertension, but does not reverse it once established: a study in Cyp1a1-Ren-2 transgenic rats. Journal of hypertension 20161001
Pharmacokinetics, pharmacodynamics and adverse event profile of GSK2256294, a novel soluble epoxide hydrolase inhibitor. British journal of clinical pharmacology 20160501
Pathophysiology of the hepoxilins. Biochimica et biophysica acta 20150401
A lipid mediator hepoxilin A3 is a natural inducer of neutrophil extracellular traps in human neutrophils. Mediators of inflammation 20150101
Acute mercury toxicity modulates cytochrome P450, soluble epoxide hydrolase and their associated arachidonic acid metabolites in C57Bl/6 mouse heart. Toxicology letters 20140407
Novel orally active epoxyeicosatrienoic acid (EET) analogs attenuate cisplatin nephrotoxicity. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20130801
Adenosine A2A receptor modulates vascular response in soluble epoxide hydrolase-null mice through CYP-epoxygenases and PPARγ. American journal of physiology. Regulatory, integrative and comparative physiology 20130101
Hepoxilin A(3) facilitates neutrophilic breach of lipoxygenase-expressing airway epithelial barriers. Journal of immunology (Baltimore, Md. : 1950) 20121115
Upregulation of cytochrome P450 2J3/11,12-epoxyeicosatrienoic acid inhibits apoptosis in neonatal rat cardiomyocytes by a caspase-dependent pathway. Cytokine 20121101
The protective effect of astrocyte-derived 14,15-epoxyeicosatrienoic acid on hydrogen peroxide-induced cell injury in astrocyte-dopaminergic neuronal cell line co-culture. Neuroscience 20121025
EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides. Journal of lipid research 20121001
Disturbed ratio of renal 20-HETE/EETs is involved in androgen-induced hypertension in cytochrome P450 4F2 transgenic mice. Gene 20120901
Activity restriction, impaired capillary function, and the development of insulin resistance in lean primates. American journal of physiology. Endocrinology and metabolism 20120901
Genetic disruption of soluble epoxide hydrolase is protective against streptozotocin-induced diabetic nephropathy. American journal of physiology. Endocrinology and metabolism 20120901
High levels of stearic acid, palmitoleic acid, and dihomo-γ-linolenic acid and low levels of linoleic acid in serum cholesterol ester are associated with high insulin resistance. Nutrition research (New York, N.Y.) 20120901
Soluble epoxide hydrolase: sex differences and role in endothelial cell survival. Arteriosclerosis, thrombosis, and vascular biology 20120801
Delivery of AAV2-CYP2J2 protects remnant kidney in the 5/6-nephrectomized rat via inhibition of apoptosis and fibrosis. Human gene therapy 20120701
Role of PI3Kα and sarcolemmal ATP-sensitive potassium channels in epoxyeicosatrienoic acid mediated cardioprotection. Journal of molecular and cellular cardiology 20120701
Oral supplementation with dihomo-γ-linolenic acid (DGLA)-enriched oil increases serum DGLA content in healthy adults. Lipids 20120601
Attenuation of cisplatin-induced renal injury by inhibition of soluble epoxide hydrolase involves nuclear factor κB signaling. The Journal of pharmacology and experimental therapeutics 20120601
Exogenous arachidonate restores the dimethoate-induced inhibition of steroidogenesis in rat interstitial cells. Lipids 20120601
Activation of JNK/c-Jun is required for the proliferation, survival, and angiogenesis induced by EET in pulmonary artery endothelial cells. Journal of lipid research 20120601
Evaluation of cytochrome P450-derived eicosanoids in humans with stable atherosclerotic cardiovascular disease. Atherosclerosis 20120601
Inhibitory effect of 5,8,11-eicosatrienoic acid on angiogenesis. Prostaglandins, leukotrienes, and essential fatty acids 20120601
5,6-EET is released upon neuronal activity and induces mechanical pain hypersensitivity via TRPA1 on central afferent terminals. The Journal of neuroscience : the official journal of the Society for Neuroscience 20120502
Ethnicity, plasma phospholipid fatty acid composition and inflammatory/endothelial activation biomarkers in the Multi-Ethnic Study of Atherosclerosis (MESA). European journal of clinical nutrition 20120501
Pyramidal cells and cytochrome P450 epoxygenase products in the neurovascular coupling response to basal forebrain cholinergic input. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20120501
Paraoxonase1 deficiency in mice is associated with hypotension and increased levels of 5,6-epoxyeicosatrienoic acid. Atherosclerosis 20120501
11,12,20-Trihydroxy-eicosa-8(Z)-enoic acid: a selective inhibitor of 11,12-EET-induced relaxations of bovine coronary and rat mesenteric arteries. American journal of physiology. Heart and circulatory physiology 20120415
Maintenance of arachidonic acid and evidence of Δ5 desaturation in cats fed γ-linolenic and linoleic acid enriched diets. Lipids 20120401
Homocysteine upregulates soluble epoxide hydrolase in vascular endothelium in vitro and in vivo. Circulation research 20120316
Relative contribution of cyclooxygenases, epoxyeicosatrienoic acids, and pH to the cerebral blood flow response to vibrissal stimulation. American journal of physiology. Heart and circulatory physiology 20120301
Epoxyeicosatrienoic acids protect rat hearts against tumor necrosis factor-α-induced injury. Journal of lipid research 20120301
The shunting of arachidonic acid metabolism to 5-lipoxygenase and cytochrome p450 epoxygenase antagonizes the anti-cancer effect of cyclooxygenase-2 inhibition in head and neck cancer cells. Cellular oncology (Dordrecht) 20120201
Differences in arachidonic acid levels and fatty acid desaturase (FADS) gene variants in African Americans and European Americans with diabetes or the metabolic syndrome. The British journal of nutrition 20120201
Relationship of serum fatty acid composition and desaturase activity to C-reactive protein in Japanese men and women. Atherosclerosis 20120201
A soluble epoxide hydrolase inhibitor--8-HUDE increases pulmonary vasoconstriction through inhibition of K(ATP) channels. Pulmonary pharmacology & therapeutics 20120201
8R-Lipoxygenase-catalyzed synthesis of a prominent cis-epoxyalcohol from dihomo-γ-linolenic acid: a distinctive transformation compared with S-lipoxygenases. Journal of lipid research 20120201
Epoxyeicosatrienoic acids and heme oxygenase-1 interaction attenuates diabetes and metabolic syndrome complications. Prostaglandins & other lipid mediators 20120101
Multiple roles of dihomo-γ-linolenic acid against proliferation diseases. Lipids in health and disease 20120101
8,9-Epoxyeicosatrienoic acid inhibits antibody production of B lymphocytes in mice. PloS one 20120101
11,12-EET stimulates the association of BK channel α and β(1) subunits in mitochondria to induce pulmonary vasoconstriction. PloS one 20120101
Plasma fatty acid composition in patients with pancreatic cancer: correlations to clinical parameters. Nutrition and cancer 20120101
Sonodynamic and photodynamic mechanisms of action of the novel hypocrellin sonosensitizer, SL017: mitochondrial cell death is attenuated by 11, 12-epoxyeicosatrienoic acid. Investigational new drugs 20111201
Erythrocyte membrane phospholipid polyunsaturated fatty acids are related to plasma C-reactive protein and adiponectin in middle-aged German women and men. European journal of nutrition 20111201
Cytochrome P450 metabolites of arachidonic acid are elevated in stroke patients compared with healthy controls. Clinical science (London, England : 1979) 20111201
Abdominal surgical incision induces remote preconditioning of trauma (RPCT) via activation of bradykinin receptors (BK2R) and the cytochrome P450 epoxygenase pathway in canine hearts. Cardiovascular drugs and therapy 20111201
EET signaling in cancer. Cancer metastasis reviews 20111201
Effects of dynamic exercise on plasma arachidonic acid epoxides and diols in human volunteers. International journal of sport nutrition and exercise metabolism 20111201
Cytochrome P450 epoxygenase CYP2J2 attenuates nephropathy in streptozotocin-induced diabetic mice. Prostaglandins & other lipid mediators 20111101
Crosstalk between EET and HO-1 downregulates Bach1 and adipogenic marker expression in mesenchymal stem cell derived adipocytes. Prostaglandins & other lipid mediators 20111101
Improved bioavailability of epoxyeicosatrienoic acids reduces TP-receptor agonist-induced tension in human bronchi. American journal of physiology. Lung cellular and molecular physiology 20111101
Epoxyeicosatrienoic acids attenuate reactive oxygen species level, mitochondrial dysfunction, caspase activation, and apoptosis in carcinoma cells treated with arsenic trioxide. The Journal of pharmacology and experimental therapeutics 20111101
Soluble epoxide hydrolase inhibition, epoxygenated fatty acids and nociception. Prostaglandins & other lipid mediators 20111101
11,12-EET increases porto-sinusoidal resistance and may play a role in endothelial dysfunction of portal hypertension. Prostaglandins & other lipid mediators 20111101
Differential effect of amyloid β on the cytochrome P450 epoxygenase activity in rat brain. Neuroscience 20111027
Reversible controlled assembly of thermosensitive polymer-coated gold nanoparticles. Langmuir : the ACS journal of surfaces and colloids 20111018
Models of neurovascular coupling via potassium and EET signalling. Journal of theoretical biology 20111007
Regulation of forskolin-induced cAMP production by cytochrome P450 epoxygenase metabolites of arachidonic acid in HEK293 cells. Cell biology and toxicology 20111001
Soluble epoxide hydrolase contamination of specific catalase preparations inhibits epoxyeicosatrienoic acid vasodilation of rat renal arterioles. American journal of physiology. Renal physiology 20111001
P-450-dependent epoxygenase pathway of arachidonic acid is involved in myeloma-induced angiogenesis of endothelial cells. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20111001
Terminal fatty-acyl-CoA desaturase involved in sex pheromone biosynthesis in the winter moth (Operophtera brumata). Insect biochemistry and molecular biology 20110901
Effects of cytochrome P-450 metabolites of arachidonic acid on the epithelial sodium channel (ENaC). American journal of physiology. Renal physiology 20110901
Development of a semi-automated LC/MS/MS method for the simultaneous quantitation of 14,15-epoxyeicosatrienoic acid, 14,15-dihydroxyeicosatrienoic acid, leukotoxin and leukotoxin diol in human plasma as biomarkers of soluble epoxide hydrolase activity in vivo. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110901
Epoxyeicosatrienoic acid-dependent cerebral vasodilation evoked by metabotropic glutamate receptor activation in vivo. American journal of physiology. Heart and circulatory physiology 20110801
Increased myoendothelial gap junctions mediate the enhanced response to epoxyeicosatrienoic acid and acetylcholine in mesenteric arterial vessels of cirrhotic rats. Liver international : official journal of the International Association for the Study of the Liver 20110701
Increases in plasma trans-EETs and blood pressure reduction in spontaneously hypertensive rats. American journal of physiology. Heart and circulatory physiology 20110601
Hepoxilin A(3) protects β-cells from apoptosis in contrast to its precursor, 12-hydroperoxyeicosatetraenoic acid. Biochimica et biophysica acta 20110601
CYP3A4 mediates growth of estrogen receptor-positive breast cancer cells in part by inducing nuclear translocation of phospho-Stat3 through biosynthesis of (±)-14,15-epoxyeicosatrienoic acid (EET). The Journal of biological chemistry 20110520
20-Iodo-14,15-epoxyeicosa-8(Z)-enoyl-3-azidophenylsulfonamide: photoaffinity labeling of a 14,15-epoxyeicosatrienoic acid receptor. Biochemistry 20110510
Anandamide oxidation by wild-type and polymorphically expressed CYP2B6 and CYP2D6. Drug metabolism and disposition: the biological fate of chemicals 20110501
Characterization of free radicals formed from COX-catalyzed DGLA peroxidation. Free radical biology & medicine 20110501
Development of an online SPE-LC-MS-based assay using endogenous substrate for investigation of soluble epoxide hydrolase (sEH) inhibitors. Analytical and bioanalytical chemistry 20110501
Selection of a DGLA-producing mutant of the microalga Parietochloris incisa: I. Identification of mutation site and expression of VLC-PUFA biosynthesis genes. Applied microbiology and biotechnology 20110401
Mammalian soluble epoxide hydrolase is identical to liver hepoxilin hydrolase. Journal of lipid research 20110401
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Role of arachidonic acid lipoxygenase metabolites in acetylcholine-induced relaxations of mouse arteries. American journal of physiology. Heart and circulatory physiology 20110301
Cytochrome P450 eicosanoids and cerebral vascular function. Expert reviews in molecular medicine 20110301
Cytochrome P450-derived epoxyeicosatrienoic acids and pulmonary hypertension: central role of transient receptor potential C6 channels. Journal of cardiovascular pharmacology 20110201
Cardioprotective effect of a dual acting epoxyeicosatrienoic acid analogue towards ischaemia reperfusion injury. British journal of pharmacology 20110201
Chronic treatment with epoxyeicosatrienoic acids modulates insulin signaling and prevents insulin resistance in hepatocytes. Prostaglandins & other lipid mediators 20110201
Selective eicosanoid-generating capacity of cytoplasmic phospholipase A2 in Pseudomonas aeruginosa-infected epithelial cells. American journal of physiology. Lung cellular and molecular physiology 20110201
Esophageal cancer proliferation is mediated by cytochrome P450 2C9 (CYP2C9). Prostaglandins & other lipid mediators 20110201
Angiotensin II regulates adrenal vascular tone through zona glomerulosa cell-derived EETs and DHETs. Hypertension (Dallas, Tex. : 1979) 20110201
14,15-Dihydroxy-eicosa-5(Z)-enoic acid selectively inhibits 14,15-epoxyeicosatrienoic acid-induced relaxations in bovine coronary arteries. The Journal of pharmacology and experimental therapeutics 20110101
Biosynthesis of 14,15-hepoxilins in human l1236 Hodgkin lymphoma cells and eosinophils. Lipids 20110101
Cytochrome P450 2J3/epoxyeicosatrienoic acids mediate the cardioprotection induced by ischaemic post-conditioning, but not preconditioning, in the rat. Clinical and experimental pharmacology & physiology 20110101
Overexpression of CYP3A4, but not of CYP2D6, promotes hypoxic response and cell growth of Hep3B cells. Drug metabolism and pharmacokinetics 20110101
The impact of FADS genetic variants on ω6 polyunsaturated fatty acid metabolism in African Americans. BMC genetics 20110101
Effects of perfluorinated fatty acids with different carbon chain length on fatty acid profiles of hepatic lipids in mice. Biological & pharmaceutical bulletin 20110101
Incorporation of n-3 PUFA and γ-linolenic acid in blood lipids and red blood cell lipids together with their influence on disease activity in patients with chronic inflammatory arthritis--a randomized controlled human intervention trial. Lipids in health and disease 20110101
Soluble epoxide hydrolase limits mechanical hyperalgesia during inflammation. Molecular pain 20110101
Elevated stearoyl-CoA desaturase in brains of patients with Alzheimer's disease. PloS one 20110101
Gene delivery of cytochrome p450 epoxygenase ameliorates monocrotaline-induced pulmonary artery hypertension in rats. American journal of respiratory cell and molecular biology 20101201
Epoxyeicosatrienoic acid agonist regulates human mesenchymal stem cell-derived adipocytes through activation of HO-1-pAKT signaling and a decrease in PPARγ. Stem cells and development 20101201
Inhibition of carcinoma cell motility by epoxyeicosatrienoic acid (EET) antagonists. Cancer science 20101201
Analysis of epoxyeicosatrienoic acids by chiral liquid chromatography/electron capture atmospheric pressure chemical ionization mass spectrometry using [13C]-analog internal standards. Rapid communications in mass spectrometry : RCM 20101130
17,18-epoxyeicosatetraenoic acid targets PPARγ and p38 mitogen-activated protein kinase to mediate its anti-inflammatory effects in the lung: role of soluble epoxide hydrolase. American journal of respiratory cell and molecular biology 20101101
Epoxyeicosatrienoates are the dominant eicosanoids in human lungs upon microbial challenge. The European respiratory journal 20101101
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
High potassium intake enhances the inhibitory effect of 11,12-EET on ENaC. Journal of the American Society of Nephrology : JASN 20101001
Overexpression of cytochrome P450 epoxygenases prevents development of hypertension in spontaneously hypertensive rats by enhancing atrial natriuretic peptide. The Journal of pharmacology and experimental therapeutics 20100901
14,15-Epoxyeicosatrienoic acid induces vasorelaxation through the prostaglandin EP(2) receptors in rat mesenteric artery. Prostaglandins & other lipid mediators 20100901
Effects of DHLA-capped CdSe/ZnS quantum dots on the fibrillation of human serum albumin. The journal of physical chemistry. B 20100826
8,9-Epoxyeicosatrienoic acid analog protects pulmonary artery smooth muscle cells from apoptosis via ROCK pathway. Experimental cell research 20100815
L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice. Drug metabolism letters 20100801
Development of a high throughput cell-based assay for soluble epoxide hydrolase using BacMam technology. Molecular biotechnology 20100701
Uptake of dihomo-gamma-linolenic acid by murine macrophages increases series-1 prostaglandin release following lipopolysaccharide treatment. Prostaglandins, leukotrienes, and essential fatty acids 20100701
Changes in fatty acid profiles in testis and spermatozoa of red deer exposed to metal pollution. Reproductive toxicology (Elmsford, N.Y.) 20100601
Evidence for a role of opioids in epoxyeicosatrienoic acid-induced cardioprotection in rat hearts. American journal of physiology. Heart and circulatory physiology 20100601
Prevention of UV-induced skin damages by 11,14,17-eicosatrienoic acid in hairless mice in vivo. Journal of Korean medical science 20100601
Skin aging and photoaging alter fatty acids composition, including 11,14,17-eicosatrienoic acid, in the epidermis of human skin. Journal of Korean medical science 20100601
Lovastatin decreases acute mucosal inflammation via 15-epi-lipoxin A4. Mucosal immunology 20100501
Epoxyeicosatrienoic acids and endothelium-dependent responses. Pflugers Archiv : European journal of physiology 20100501
Increased CYP2J3 expression reduces insulin resistance in fructose-treated rats and db/db mice. Diabetes 20100401
Pharmacological inhibition of the soluble epoxide hydrolase-from mouse to man. Current opinion in pharmacology 20100401
Direct angiotensin II type 2 receptor stimulation acts anti-inflammatory through epoxyeicosatrienoic acid and inhibition of nuclear factor kappaB. Hypertension (Dallas, Tex. : 1979) 20100401
Combined inhibition of 20-hydroxyeicosatetraenoic acid formation and of epoxyeicosatrienoic acids degradation attenuates hypertension and hypertension-induced end-organ damage in Ren-2 transgenic rats. Clinical science (London, England : 1979) 20100223
A sulfaphenazole-sensitive EDHF opposes platelet-endothelium interactions in vitro and in the hamster microcirculation in vivo. Cardiovascular research 20100201
Inhibition of soluble epoxide hydrolase preserves cardiomyocytes: role of STAT3 signaling. American journal of physiology. Heart and circulatory physiology 20100201
Impact of epoxyeicosatrienoic acids in lung ischemia-reperfusion injury. Microcirculation (New York, N.Y. : 1994) 20100201
Mildly abnormal general movement quality in infants is associated with higher Mead acid and lower arachidonic acid and shows a U-shaped relation with the DHA/AA ratio. Prostaglandins, leukotrienes, and essential fatty acids 20100101
[The role of modification of fatty acid composition of erythrocyte lipids in pathogenesis of arterial hypertension]. Kardiologiia 20100101
Vascular pharmacology of epoxyeicosatrienoic acids. Advances in pharmacology (San Diego, Calif.) 20100101
Serum cytokeratin 18 M30 antigen level and its correlation with nutritional parameters in middle-aged Japanese males with nonalcoholic fatty liver disease (NAFLD). Journal of nutritional science and vitaminology 20100101
Epoxyeicosatrienoic acid agonist rescues the metabolic syndrome phenotype of HO-2-null mice. The Journal of pharmacology and experimental therapeutics 20091201
20-125Iodo-14,15-epoxyeicosa-5(Z)-enoic acid: a high-affinity radioligand used to characterize the epoxyeicosatrienoic acid antagonist binding site. The Journal of pharmacology and experimental therapeutics 20091201
The role of neutrophils in the event of intestinal inflammation. Current opinion in pharmacology 20091201
Rapid, simultaneous quantitation of mono and dioxygenated metabolites of arachidonic acid in human CSF and rat brain. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091201
Eicosapentaenoic acid increases cytochrome P-450 2J2 gene expression and epoxyeicosatrienoic acid production via peroxisome proliferator-activated receptor γ in endothelial cells. Journal of cardiology 20091201
Identification of 13-hydroxy-14,15-epoxyeicosatrienoic acid as an acid-stable endothelium-derived hyperpolarizing factor in rabbit arteries. The Journal of biological chemistry 20091106
The hepoxilins and some analogues: a review of their biology. British journal of pharmacology 20091001
Discovery of 3,3-disubstituted piperidine-derived trisubstituted ureas as highly potent soluble epoxide hydrolase inhibitors. Bioorganic & medicinal chemistry letters 20090915
Detection of EETs and HETE-generating cytochrome P-450 enzymes and the effects of their metabolites on myometrial and vascular function. American journal of physiology. Endocrinology and metabolism 20090901
TRPV4-dependent dilation of peripheral resistance arteries influences arterial pressure. American journal of physiology. Heart and circulatory physiology 20090901
14,15-Epoxyeicosa-5,8,11-trienoic acid (14,15-EET) surrogates containing epoxide bioisosteres: influence upon vascular relaxation and soluble epoxide hydrolase inhibition. Journal of medicinal chemistry 20090827
Role of soluble epoxide hydrolase in the sex-specific vascular response to cerebral ischemia. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20090801
Associations between term birth dimensions and prenatal exposure to essential and trans fatty acids. Early human development 20090801
Role of arachidonic acid lipoxygenase metabolites in the regulation of vascular tone. American journal of physiology. Heart and circulatory physiology 20090801
Anti-atherosclerotic effects of dihomo-gamma-linolenic acid in ApoE-deficient mice. Journal of atherosclerosis and thrombosis 20090801
Role of B-type natriuretic peptide in epoxyeicosatrienoic acid-mediated improved post-ischaemic recovery of heart contractile function. Cardiovascular research 20090715
Evidence for role of epoxyeicosatrienoic acids in mediating ischemic preconditioning and postconditioning in dog. American journal of physiology. Heart and circulatory physiology 20090701
Ethnic differences in early pregnancy maternal n-3 and n-6 fatty acid concentrations: an explorative analysis. The British journal of nutrition 20090601
An alternate pathway to long-chain polyunsaturates: the FADS2 gene product Delta8-desaturates 20:2n-6 and 20:3n-3. Journal of lipid research 20090601
Subchronic (13-week) oral toxicity study of dihomo-gamma-linolenic acid (DGLA) oil in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090601
Epoxyeicosatrienoic acids limit damage to mitochondrial function following stress in cardiac cells. Journal of molecular and cellular cardiology 20090601
Protective actions of epoxyeicosatrienoic acid: dual targeting of cardiovascular PI3K and KATP channels. Journal of molecular and cellular cardiology 20090601
8,9-Epoxyeicosatrienoic acid protects the glomerular filtration barrier. Prostaglandins & other lipid mediators 20090601
Oral supplementation with dihomo-gamma-linolenic acid-enriched oil altered serum fatty acids in healthy men. Bioscience, biotechnology, and biochemistry 20090601
Epoxyeicosanoids as mediators of neurogenic vasodilation in cerebral vessels. American journal of physiology. Heart and circulatory physiology 20090501
[Production of functional lipids by microorganisms: arachidonic acid and related polyunsaturated fatty acids]. Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20090501
A cytochrome P450-derived epoxygenated metabolite of anandamide is a potent cannabinoid receptor 2-selective agonist. Molecular pharmacology 20090401
Fatty acid CoA ligase-4 gene polymorphism influences fatty acid metabolism in metabolic syndrome, but not in depression. The Tohoku journal of experimental medicine 20090401
Dietary linoleic acid has no effect on arachidonic acid, but increases n-6 eicosadienoic acid, and lowers dihomo-gamma-linolenic and eicosapentaenoic acid in plasma of adult men. Prostaglandins, leukotrienes, and essential fatty acids 20090401
Epoxyeicosatrienoic acid activates BK channels in the cortical collecting duct. Journal of the American Society of Nephrology : JASN 20090301
Chronic hypoxia enhances 15-lipoxygenase-mediated vasorelaxation in rabbit arteries. American journal of physiology. Heart and circulatory physiology 20090301
Chronic blockade of 20-HETE synthesis reduces polycystic kidney disease in an orthologous rat model of ARPKD. American journal of physiology. Renal physiology 20090301
Glomerular 20-HETE, EETs, and TGF-beta1 in diabetic nephropathy. American journal of physiology. Renal physiology 20090301
Associations between neonatal birth dimensions and maternal essential and trans fatty acid contents during pregnancy and at delivery. The British journal of nutrition 20090201
The depressive effects of 5,8,11-eicosatrienoic Acid (20:3n-9) on osteoblasts. Lipids 20090201
Possible mediators of connecting tubule glomerular feedback. Hypertension (Dallas, Tex. : 1979) 20090201
Inhibition of the soluble epoxide hydrolase attenuates monocrotaline-induced pulmonary hypertension in rats. Journal of hypertension 20090201
Epoxyeicosatrienoic acids function as selective, endogenous antagonists of native thromboxane receptors: identification of a novel mechanism of vasodilation. The Journal of pharmacology and experimental therapeutics 20090101
Cytochrome P450 metabolites of arachidonic acid play a role in the enhanced cardiac dysfunction in diabetic rats following ischaemic reperfusion injury. Autonomic & autacoid pharmacology 20090101
Nutrition for the eye: different susceptibility of the retina and the lacrimal gland to dietary omega-6 and omega-3 polyunsaturated fatty acid incorporation. Ophthalmic research 20090101
Optimal dose of preoperative enteral immunonutrition for patients with esophageal cancer. Surgery today 20090101
Role of cytochrome P450-dependent transient receptor potential V4 activation in flow-induced vasodilatation. Cardiovascular research 20081201
Epoxyeicosatrienoic acids and the soluble epoxide hydrolase are determinants of pulmonary artery pressure and the acute hypoxic pulmonary vasoconstrictor response. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20081201
CPI-17 silencing-reduced responsiveness in control and TNF-alpha-treated human bronchi. American journal of respiratory cell and molecular biology 20081201
Inhibitory effects of epoxyeicosatrienoic acids on volume-activated chloride channels in rat mesenteric arterial smooth muscle. Prostaglandins & other lipid mediators 20081201
Failure to upregulate the adenosine2A receptor-epoxyeicosatrienoic acid pathway contributes to the development of hypertension in Dahl salt-sensitive rats. American journal of physiology. Renal physiology 20081201
Hypercholesterolemia enhances 15-lipoxygenase-mediated vasorelaxation and acetylcholine-induced hypotension. Arteriosclerosis, thrombosis, and vascular biology 20081201
Determination of epoxyeicosatrienoic acids in human red blood cells and plasma by GC/MS in the NICI mode. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20081201
Multidrug resistance-associated transporter 2 regulates mucosal inflammation by facilitating the synthesis of hepoxilin A3. Journal of immunology (Baltimore, Md. : 1950) 20081201
Arachidonic acid metabolites inhibit the stimulatory effect of angiotensin II in renal proximal tubules. Hypertension research : official journal of the Japanese Society of Hypertension 20081201
Cytochrome P-450 metabolites in renal circulation and excretion--interaction with the nitric oxide (NO) system. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20081201
The endocannabinoid anandamide is a substrate for the human polymorphic cytochrome P450 2D6. The Journal of pharmacology and experimental therapeutics 20081101
Role of cytochrome P450 2C8 and 2J2 genotypes in calcineurin inhibitor-induced chronic kidney disease. Pharmacogenetics and genomics 20081101
Epoxyeicosatrienoic acids are part of the VEGF-activated signaling cascade leading to angiogenesis. American journal of physiology. Cell physiology 20081101
Role of CYP epoxygenases in A2A AR-mediated relaxation using A2A AR-null and wild-type mice. American journal of physiology. Heart and circulatory physiology 20081101
Soluble epoxide hydrolase inhibition and gene deletion are protective against myocardial ischemia-reperfusion injury in vivo. American journal of physiology. Heart and circulatory physiology 20081101
[Promotive effects of epoxyeicosatrienoic acids (EETs) on proliferation of tumor cells]. Ai zheng = Aizheng = Chinese journal of cancer 20081101
Direct and simultaneous profiling of epoxyeicosatrienoic acid enantiomers by capillary tandem column chiral-phase liquid chromatography with dual online photodiode array and tandem mass spectrometric detection. Analytical and bioanalytical chemistry 20081001
Antiangiogenic effect of inhibitors of cytochrome P450 on rats with glioblastoma multiforme. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20080801
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Interaction of nitric oxide, 20-HETE, and EETs during functional hyperemia in whisker barrel cortex. American journal of physiology. Heart and circulatory physiology 20080801
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COX-2 inhibitors and metabolism of essential fatty acids. Medical science monitor : international medical journal of experimental and clinical research 20050701
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The hepoxilin analog, PBT-3, inhibits growth of K-562 CML solid tumours in vivo in nude mice. In vivo (Athens, Greece) 20050101
Not so EEZE: the 'EDHF' antagonist 14, 15 epoxyeicosa-5(Z)-enoic acid has vasodilator properties in mesenteric arteries. European journal of pharmacology 20041215
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Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants. Nature biotechnology 20040601
Developmental changes in myoendothelial gap junction mediated vasodilator activity in the rat saphenous artery. The Journal of physiology 20040501
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Membrane-potential-dependent inhibition of platelet adhesion to endothelial cells by epoxyeicosatrienoic acids. Arteriosclerosis, thrombosis, and vascular biology 20040301
Role of EETs in regulation of endothelial permeability in rat lung. American journal of physiology. Lung cellular and molecular physiology 20040201
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A peroxisome proliferator-activated receptor-alpha activator induces renal CYP2C23 activity and protects from angiotensin II-induced renal injury. The American journal of pathology 20040201
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The thromboxane receptor antagonist PBT-3, a hepoxilin stable analog, selectively antagonizes the TPalpha isoform in transfected COS-7 cells. The Journal of pharmacology and experimental therapeutics 20031201
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Hepoxilins and trioxilins in barnacles: an analysis of their potential roles in egg hatching and larval settlement. The Journal of experimental biology 20030901
11,12-Epoxyeicosatrienoic acid-induced inhibition of FOXO factors promotes endothelial proliferation by down-regulating p27Kip1. The Journal of biological chemistry 20030808
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Increased epoxyeicosatrienoic acid formation in the rat kidney during liver cirrhosis. Journal of the American Society of Nephrology : JASN 20030701
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Effects of eicosatrienoic acid (20:3 n-9, Mead's acid) on some promalignant-related properties of three human cancer cell lines. Prostaglandins & other lipid mediators 20030701
Metabolism of 12-hydroperoxyeicosatetraenoic acid to vasodilatory trioxilin C3 by rabbit aorta. Biochimica et biophysica acta 20030620
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Contributions of nitric oxide, EDHF, and EETs to endothelium-dependent relaxation in renal afferent arterioles. Kidney international 20030601
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The regulation of arachidonic acid metabolism in human first trimester trophoblast by cyclic AMP. Prostaglandins & other lipid mediators 20030401
Effect of DHLA on response of isolated rat urinary bladder to repetitive field stimulation. Molecular and cellular biochemistry 20030401
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The nitric oxide- and prostaglandin-independent component of the renal vasodilator effect of thimerosal is mediated by epoxyeicosatrienoic acids. The Journal of pharmacology and experimental therapeutics 20030301
Endothelium-derived hyperpolarizing factor in human internal mammary artery is 11,12-epoxyeicosatrienoic acid and causes relaxation by activating smooth muscle BK(Ca) channels. Circulation 20030211
Comparison of vasodilatory properties of 14,15-EET analogs: structural requirements for dilation. American journal of physiology. Heart and circulatory physiology 20030101
Epoxygenase-driven angiogenesis in human lung microvascular endothelial cells. American journal of physiology. Heart and circulatory physiology 20030101
Block of erg current by linoleoylamide, a sleep-inducing agent, in pituitary GH3 cells. European journal of pharmacology 20030101
A lipoxygenase product, hepoxilin A(3), enhances nerve growth factor-dependent neurite regeneration post-axotomy in rat superior cervical ganglion neurons in vitro. Neuroscience 20030101
Eicosanoid precursor polyenoic fatty acids modulate synaptic levels of dopamine in ex-vivo slices of rat brain striatum. In vivo (Athens, Greece) 20030101
Cytochrome P450-derived eicosanoids mediators of ocular surface inflammation. are. Advances in experimental medicine and biology 20030101
Beneficial effects of n-9 eicosatrienoic acid on experimental bowel lesions. Surgery today 20030101
The hepoxilin analog PBT-3 induces apoptosis in BCR-ABL-positive K562 leukemia cells. Anticancer research 20030101
The hepoxilin stable analogue, PBT-3, inhibits primary, platelet-related hemostasis in whole blood measured in vitro with the PFA-100. Thrombosis research 20030101
Human coronary endothelial cells convert 14,15-EET to a biologically active chain-shortened epoxide. American journal of physiology. Heart and circulatory physiology 20021201
Cerebral capillary endothelial cell mitogenesis and morphogenesis induced by astrocytic epoxyeicosatrienoic Acid. Stroke 20021201
Modulation of microphthalmia-associated transcription factor gene expression alters skin pigmentation. The Journal of investigative dermatology 20021201
Capillary electrophoresis of cytochrome P-450 epoxygenase metabolites of arachidonic acid. 2. Resolution of stereoisomers. Analytical chemistry 20021115
Evidence for a membrane site of action for 14,15-EET on expression of aromatase in vascular smooth muscle. American journal of physiology. Heart and circulatory physiology 20021101
Suppression of cortical functional hyperemia to vibrissal stimulation in the rat by epoxygenase inhibitors. American journal of physiology. Heart and circulatory physiology 20021101
Stereospecific activation of cardiac ATP-sensitive K(+) channels by epoxyeicosatrienoic acids: a structural determinant study. Molecular pharmacology 20021101
Production of 5,8,11-eicosatrienoic acid by a delta5 and delta6 desaturation activity-enhanced mutant derived from a delta12 desaturation activity-defective mutant of Mortierella alpina 1S-4. Applied microbiology and biotechnology 20021101
Assessment of essential fatty acid and omega3-fatty acid status by measurement of erythrocyte 20:3omega9 (Mead acid), 22:5omega6/20:4omega6 and 22:5omega6/22:6omega3. Prostaglandins, leukotrienes, and essential fatty acids 20021101
Trans isomeric octadecenoic acids are related inversely to arachidonic acid and DHA and positively related to mead acid in umbilical vessel wall lipids. Lipids 20021001
Role of 5,6-epoxyeicosatrienoic acid in the regulation of newborn piglet pulmonary vascular tone. American journal of physiology. Lung cellular and molecular physiology 20020801
The production of progesterone and 5,6-epoxyeicosatrienoic acid by human granulosa cells. The Journal of steroid biochemistry and molecular biology 20020801
Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. The Biochemical journal 20020715
To move or not to move? Cytochrome P450 products and cell migration. Circulation research 20020517
Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids. Circulation research 20020517
14,15-Epoxyeicosa-5(Z)-enoic acid: a selective epoxyeicosatrienoic acid antagonist that inhibits endothelium-dependent hyperpolarization and relaxation in coronary arteries. Circulation research 20020517
Calcium influx factor from cytochrome P-450 metabolism and secretion-like coupling mechanisms for capacitative calcium entry in corneal endothelial cells. The Journal of biological chemistry 20020510
Cytochrome P450 2C9-induced endothelial cell proliferation involves induction of mitogen-activated protein (MAP) kinase phosphatase-1, inhibition of the c-Jun N-terminal kinase, and up-regulation of cyclin D1. The Journal of biological chemistry 20020503
Polyunsaturated fatty acid biosynthesis from [1-14C]20:3 n-6 acid in rat cultured Sertoli cells. Linoleic acid effect. The international journal of biochemistry & cell biology 20020501
14,15-Dihydroxyeicosatrienoic acid relaxes bovine coronary arteries by activation of K(Ca) channels. American journal of physiology. Heart and circulatory physiology 20020501
Hepoxilin analogs inhibit bleomycin-induced pulmonary fibrosis in the mouse. The Journal of pharmacology and experimental therapeutics 20020501
A new family of thromboxane receptor antagonists with secondary thromboxane synthase inhibition. The Journal of pharmacology and experimental therapeutics 20020501
Effects of epoxyeicosatrienoic acids on polymorphonuclear leukocyte function. Life sciences 20020421
Dynamic modulation of interendothelial gap junctional communication by 11,12-epoxyeicosatrienoic acid. Circulation research 20020419
Role of ADP-ribose in 11,12-EET-induced activation of K(Ca) channels in coronary arterial smooth muscle cells. American journal of physiology. Heart and circulatory physiology 20020401
The hepoxilin analog PBT-3 inhibits heparin-activated platelet aggregation evoked by ADP. FEBS letters 20020327
Functional reconstitution of an eicosanoid-modulated Cl- channel from bovine tracheal smooth muscle. American journal of physiology. Cell physiology 20020301
Peroxynitrite reaction with the reduced and the oxidized forms of lipoic acid: new insights into the reaction of peroxynitrite with thiols. Archives of biochemistry and biophysics 20020101
P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiological reviews 20020101
Hepoxilin B3 and its enzymatically formed derivative trioxilin B3 are incorporated into phospholipids in psoriatic lesions. The Journal of investigative dermatology 20020101
Substrate down regulation of 12-lipoxygenase in human platelets. Advances in experimental medicine and biology 20020101
Development of enzyme immunoassays for 5,6-, 8,9-, 11,12-, and 14,15- EETs and the corresponding DHETs. Advances in experimental medicine and biology 20020101
Activation of ATP-sensitive K(+) channels by epoxyeicosatrienoic acids in rat cardiac ventricular myocytes. The Journal of physiology 20011215
Cyclic stretch enhances the expression and activity of coronary endothelium-derived hyperpolarizing factor synthase. Hypertension (Dallas, Tex. : 1979) 20011201
Epoxyeicosatrienoic acids (EET(11,12)) may partially restore endothelium-derived hyperpolarizing factor-mediated function in coronary microarteries. The Annals of thoracic surgery 20011201
Vicinal nitrohydroxyeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid. The Journal of pharmacology and experimental therapeutics 20011101
A critical review of the role of endothelial factors in the pathogenesis of hypertension. Journal of cardiovascular pharmacology 20011101
Cytochrome p450 and vascular homeostasis. Circulation research 20011026
Epoxyeicosatrienoic acid-induced relaxation is impaired in insulin resistance. American journal of physiology. Heart and circulatory physiology 20011001
Stereospecific synthesis of trans-arachidonic acids. Bioorganic & medicinal chemistry letters 20010917
Hypothalamic 11,12-epoxyeicosatrienoic acid attenuates fever induced by central interleukin-1beta in the rat. Neuroscience letters 20010914
Dihydroxyeicosatrienoic acids are potent activators of Ca(2+)-activated K(+) channels in isolated rat coronary arterial myocytes. The Journal of physiology 20010801
Nitric oxide synthase activity in neutrophils from patients with localized aggressive periodontitis. Journal of periodontology 20010801
Mediation of EDHF-induced reduction of smooth muscle [Ca(2+)](i) and arteriolar dilation by K(+) channels, 5,6-EET, and gap junctions. Microcirculation (New York, N.Y. : 1994) 20010801
Identifying endothelium-derived hyperpolarizing factor: recent approaches to assay the role of epoxyeicosatrienoic acids. Japanese journal of pharmacology 20010801
The coronary endothelium-derived hyperpolarizing factor (EDHF) stimulates multiple signalling pathways and proliferation in vascular cells. Pflugers Archiv : European journal of physiology 20010701
EET homologs potently dilate coronary microvessels and activate BK(Ca) channels. American journal of physiology. Heart and circulatory physiology 20010601
EDHF mediates flow-induced dilation in skeletal muscle arterioles of female eNOS-KO mice. American journal of physiology. Heart and circulatory physiology 20010601
Cytochrome P-450 metabolite of arachidonic acid mediates bradykinin-induced negative inotropic effect. American journal of physiology. Heart and circulatory physiology 20010601
Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids. The Journal of biological chemistry 20010511
Gap junction-dependent increases in smooth muscle cAMP underpin the EDHF phenomenon in rabbit arteries. Biochemical and biophysical research communications 20010511
Pathways of epoxyeicosatrienoic acid metabolism in endothelial cells. Implications for the vascular effects of soluble epoxide hydrolase inhibition. The Journal of biological chemistry 20010504
EETs relax airway smooth muscle via an EpDHF effect: BK(Ca) channel activation and hyperpolarization. American journal of physiology. Lung cellular and molecular physiology 20010501
Determination of cytochrome P450 metabolites of arachidonic acid in coronary venous plasma during ischemia and reperfusion in dogs. Analytical biochemistry 20010501
Enhanced renal microvascular reactivity to angiotensin II in hypertension is ameliorated by the sulfonimide analog of 11,12-epoxyeicosatrienoic acid. Journal of hypertension 20010501
Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma -linolenic acid with prostaglandin endoperoxide H synthases. The Journal of biological chemistry 20010330
Effects of converting enzyme inhibitors on renal P-450 metabolism of arachidonic acid. American journal of physiology. Regulatory, integrative and comparative physiology 20010301
Endothelium-independent, ouabain-sensitive relaxation of bovine coronary arteries by EETs. American journal of physiology. Heart and circulatory physiology 20010301
Epoxyeicosatrienoic acid-mediated renal vasodilation to arachidonic acid is enhanced in SHR. Hypertension (Dallas, Tex. : 1979) 20010301
Inhibitors of arachidonic acid metabolism have variable effects on calcium signaling pathways. American journal of hypertension 20010301
Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3. Archives of biochemistry and biophysics 20010301
Effects of polyunsaturated fatty acids on atrophic gastritis in a Japanese population. Cancer letters 20010226
Modifications in mitochondrial metabolism and ultrastructure and their relationship to tumour growth inhibition by gamma-linolenic acid. Molecular and cellular biochemistry 20010201
Binding of cytochrome P450 monooxygenase and lipoxygenase pathway products by heart fatty acid-binding protein. Biochemistry 20010130
Endothelium-derived hyperpolarizing factor synthase (Cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circulation research 20010119
Evidence for the presence of phospholipid hydroperoxide glutathione peroxidase in human platelets: implications for its involvement in the regulatory network of the 12-lipoxygenase pathway of arachidonic acid metabolism. The Biochemical journal 20010101
The lung HETEs (and EETs) up. American journal of physiology. Heart and circulatory physiology 20010101
Regulation of BK(Ca) channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid. Molecular pharmacology 20010101
Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin. Journal of vascular research 20010101
Dual regulation of the cerebral microvasculature by epoxyeicosatrienoic acids. Trends in cardiovascular medicine 20010101
Longitudinal study of fatty acids in plasma and erythrocyte phospholipids during pregnancy. Journal of perinatal medicine 20010101
Investigation of long-chain polyunsaturated fatty acid metabolism in lactating women by means of stable isotope techniques. Advances in experimental medicine and biology 20010101
Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland. Nutrition and cancer 20010101
Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circulation research 20001124

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