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Epoxygenase

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https://www.readbyqxmd.com/read/27891824/lipidomic-profiling-of-high-fat-diet-induced-obesity-in-mice-importance-of-cytochrome-p450-derived-fatty-acid-epoxides
#1
Weicang Wang, Jun Yang, Weipeng Qi, Haixia Yang, Chang Wang, Bowen Tan, Bruce D Hammock, Yeonhwa Park, Daeyoung Kim, Guodong Zhang
OBJECTIVE: Enzymatic metabolism of polyunsaturated fatty acids leads to formation of bioactive lipid metabolites (LMs). Previous studies have shown that obesity leads to deregulation of LMs in adipose tissues. However, most previous studies have focused on a single or limited number of LMs, and few systematical analyses have been carried out. METHODS: A LC-MS/MS-based lipidomics approach was used, which can analyze >100 LMs produced by cyclooxygenase, lipoxygenase, and cytochrome P450 (CYP) enzymes, to analyze the profile of LMs in high-fat diet-induced obesity in mice...
November 28, 2016: Obesity
https://www.readbyqxmd.com/read/27878278/alteration-of-epoxyeicosatrienoic-acids-in-the-liver-and-kidney-of-cytochrome-p450-4f2-transgenic-mice
#2
Bijun Zhang, Guangrui Lai, Xiaoliang Liu, Yanyan Zhao
Arachidonic acid (AA) can be metabolized into 20-hydroxyeicosatetraenoic acid (20-HETE) by ω-hydroxylases, and epoxyeicosatrienoic acids (EETs) by epoxygenases. The effects of EETs in cardiovascular physiology are vasodilatory, anti-inflammatory and anti‑apoptotic, which are opposite to the function to 20‑HETE. However, EETs are not stable in vivo, and are rapidly degraded to the biologically less active metabolites, dihydroxyeicosatrienoic acids, via soluble epoxide hydrolase (sEH). Western blotting, reverse transcription‑quantitative polymerase chain reaction and liquid chromatography tandem mass spectrometry were performed in order to determine target RNA and protein expression levels...
November 23, 2016: Molecular Medicine Reports
https://www.readbyqxmd.com/read/27791151/targeting-cyp2j-to-reduce-paclitaxel-induced-peripheral-neuropathic-pain
#3
Marco Sisignano, Carlo Angioni, Chul-Kyu Park, Sascha Meyer Dos Santos, Holger Jordan, Maria Kuzikov, Di Liu, Sebastian Zinn, Stephan W Hohman, Yannick Schreiber, Béla Zimmer, Mike Schmidt, Ruirui Lu, Jing Suo, Dong-Dong Zhang, Stephan M G Schäfer, Martine Hofmann, Ajay S Yekkirala, Natasja de Bruin, Michael J Parnham, Clifford J Woolf, Ru-Rong Ji, Klaus Scholich, Gerd Geisslinger
Chemotherapy-induced peripheral neuropathic pain (CIPNP) is a severe dose- and therapy-limiting side effect of widely used cytostatics that is particularly difficult to treat. Here, we report increased expression of the cytochrome-P450-epoxygenase CYP2J6 and increased concentrations of its linoleic acid metabolite 9,10-EpOME (9,10-epoxy-12Z-octadecenoic acid) in dorsal root ganglia (DRGs) of paclitaxel-treated mice as a model of CIPNP. The lipid sensitizes TRPV1 ion channels in primary sensory neurons and causes increased frequency of spontaneous excitatory postsynaptic currents in spinal cord nociceptive neurons, increased CGRP release from sciatic nerves and DRGs, and a reduction in mechanical and thermal pain hypersensitivity...
November 1, 2016: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/27782740/vasodilatory-responses-of-renal-interlobular-arteries-to-epoxyeicosatrienoic-acids-analog-are-not-enhanced-in-ren-2-transgenic-hypertensive-rats-evidence-against-a-role-of-direct-vascular-effects-of-epoxyeicosatrienoic-acids-in-progression-of-experimental-heart
#4
A Sporková, Z Husková, P Škaroupková, N R Reddy, J R Falck, J Sadowski, L Červenka
Pathophysiological mechanisms underlying the development of renal dysfunction and progression of congestive heart failure (CHF) remain poorly understood. Recent studies have revealed striking differences in the role of epoxyeicosatrienoic acids (EETs), active products of cytochrome P-450-dependent epoxygenase pathway of arachidonic acid, in the progression of aorto-caval fistula (ACF)-induced CHF between hypertensive Ren-2 renin transgenic rats (TGR) and transgene-negative normotensive Hannover Sprague-Dawley (HanSD) controls...
October 26, 2016: Physiological Research
https://www.readbyqxmd.com/read/27720395/fenofibrate-inhibits-cytochrome-p450-epoxygenase-2c-activity-to-suppress-pathological-ocular-angiogenesis
#5
Yan Gong, Zhuo Shao, Zhongjie Fu, Matthew L Edin, Ye Sun, Raffael G Liegl, Zhongxiao Wang, Chi-Hsiu Liu, Samuel B Burnim, Steven S Meng, Fred B Lih, John Paul SanGiovanni, Darryl C Zeldin, Ann Hellström, Lois E H Smith
Neovascular eye diseases including retinopathy of prematurity, diabetic retinopathy and age-related-macular-degeneration are major causes of blindness. Fenofibrate treatment in type 2 diabetes patients reduces progression of diabetic retinopathy independent of its peroxisome proliferator-activated receptor (PPAR)α agonist lipid lowering effect. The mechanism is unknown. Fenofibrate binds to and inhibits cytochrome P450 epoxygenase (CYP)2C with higher affinity than to PPARα. CYP2C metabolizes ω-3 long-chain polyunsaturated fatty acids (LCPUFAs)...
September 30, 2016: EBioMedicine
https://www.readbyqxmd.com/read/27683613/cyp2c44-gene-disruption-exacerbated-pulmonary-hypertension-and-heart-failure-in-female-but-not-male-mice
#6
Sachindra Raj Joshi, Anand Lakhkar, Vidhi Dhagia, Ariadne L Zias, Vasiliki Soldatos, Kaori Oshima, Houli Jiang, Katherine Gotlinger, Jorge H Capdevila, Michal L Schwartzman, Ivan F McMurtry, Sachin A Gupte
Epoxyeicosatrienoicacids (EETs), synthesized from arachidonic acid by epoxygenases of the CYP2C and CYP2J gene subfamilies, contribute to hypoxic pulmonary vasoconstriction (HPV) in mice. Despite their roles in HPV, it is controversial whether EETs mediate or ameliorate pulmonary hypertension (PH). A recent study showed that deficiency of Cyp2j did not protect male and female mice from hypoxia-induced PH. Since CYP2C44 is a functionally important epoxygenase, we hypothesized that knockout of the Cyp2c44 gene would protect both sexes of mice from hypoxia-induced PH...
September 2016: Pulmonary Circulation
https://www.readbyqxmd.com/read/27669111/progression-of-hypertension-and-kidney-disease-in-aging-fawn-hooded-rats-is-mediated-by-enhanced-influence-of-renin-angiotensin-system-and-suppression-of-nitric-oxide-system-and-epoxyeicosanoids
#7
Šárka Doleželová, Šárka Jíchová, Zuzana Husková, Alžběta Vojtíšková, Petr Kujal, Lenka Hošková, Josef Kautzner, Janusz Sadowski, Luděk Červenka, Libor Kopkan
The fawn-hooded hypertensive (FHH) rat serves as a genetic model of spontaneous hypertension associated with glomerular hyperfiltration and proteinuria. However, the knowledge of the natural course of hypertension and kidney disease in FHH rats remains fragmentary and the underlying pathophysiological mechanisms are unclear. In this study, over the animals' lifetime, we followed the survival rate, blood pressure (telemetry), indices of kidney damage, the activity of renin-angiotensin (RAS) and nitric oxide (NO) systems, and CYP450-epoxygenase products (EETs)...
2016: Clinical and Experimental Hypertension: CHE
https://www.readbyqxmd.com/read/27663770/association-of-cyp2c19-variants-and-epoxyeicosatrienoic-acids-on-patients-with-microvascular-angina
#8
Tomonori Akasaka, Daisuke Sueta, Yuichiro Arima, Noriaki Tabata, Seiji Takashio, Yasuhiro Izumiya, Eiichiro Yamamoto, Megumi Yamamuro, Kenichi Tsujita, Sunao Kojima, Koichi Kaikita, Ayami Kajiwara, Kazunori Morita, Kentaro Oniki, Junji Saruwatari, Kazuko Nakagawa, Yasuhiro Ogata, Kunihiko Matsui, Seiji Hokimoto
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 association of CYP2C19 polymorphisms and EETs on microvascular angina (MVA) caused by coronary microvascular dysfunction. We examined CYP2C19 genotypes in patients with MVA (n = 71) and healthy subjects as control (n = 71)...
December 1, 2016: American Journal of Physiology. Heart and Circulatory Physiology
https://www.readbyqxmd.com/read/27596333/meloxicam-fails-to-augment-the-reno-protective-effects-of-soluble-epoxide-hydrolase-inhibition-in-streptozotocin-induced-diabetic-rats-via-increased-20-hete-levels
#9
Mohamed M Katary, Chelsey Pye, Ahmed A Elmarakby
The pro-inflammatory cyclooxygenase (COX)-derived prostaglandins and the anti-inflammatory cytochrome P450 epoxygenase-derived epoxyeicosatrienoic acids (EETs) play an important role in the regulation of renal injury. The current study examined whether COX inhibition augments the reno-protective effects of increased EETs levels via inhibiting EETs degradation by soluble epoxide hydrolase (sEH) in diabetic rats. Streptozotocin (50mg/kg, i.v) was used to induce diabetes in male Sprague Dawley rats. Rats were then divided into 5 groups (n=6-8); control non diabetic, diabetic, diabetic treated with the sEH inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid (t-AUCB), diabetic treated with the COX inhibitor meloxicam and diabetic treated with meloxicam plus t-AUCB for 2 months...
September 2, 2016: Prostaglandins & Other Lipid Mediators
https://www.readbyqxmd.com/read/27583776/effect-of-soluble-epoxide-hydrolase-on-the-modulation-of-coronary-reactive-hyperemia-role-of-oxylipins-and-ppar%C3%AE
#10
Ahmad Hanif, Matthew L Edin, Darryl C Zeldin, Christophe Morisseau, Mohammed A Nayeem
Coronary reactive hyperemia (CRH) is a physiological response to ischemic insult that prevents the potential harm associated with an interruption of blood supply. The relationship between the pharmacologic inhibition of soluble epoxide hydrolase (sEH) and CRH response to a brief ischemia is not known. sEH is involved in the main catabolic pathway of epoxyeicosatrienoic acids (EETs), which are converted into dihydroxyeicosatrienoic acids (DHETs). EETs protect against ischemia/reperfusion injury and have numerous beneficial physiological effects...
2016: PloS One
https://www.readbyqxmd.com/read/27494529/novel-roles-of-epoxyeicosanoids-in-regulating-cardiac-mitochondria
#11
Haitham E El-Sikhry, Nasser Alsaleh, Rambabu Dakarapu, John R Falck, John M Seubert
Maintenance of a healthy pool of mitochondria is important for the function and survival of terminally differentiated cells such as cardiomyocytes. Epoxyeicosatrienoic acids (EETs) are epoxy lipids derived from metabolism of arachidonic acid by cytochrome P450 epoxygenases. We have previously shown that EETs trigger a protective response limiting mitochondrial dysfunction and reducing cellular death. The aim of this study was to investigate whether EET-mediated effects influence mitochondrial quality in HL-1 cardiac cells during starvation...
2016: PloS One
https://www.readbyqxmd.com/read/27459385/cyp2j2-derived-eets-attenuated-angiotensin-ii-induced-adventitial-remodeling-via-reduced-inflammatory-response
#12
Chi Zhou, Jin Huang, Junxiong Chen, Jinsheng Lai, Fasheng Zhu, Xizhen Xu, Dao Wen Wang
BACKGROUND: Cytochrome P450 (CYP) epoxygenases metabolize arachidonic acids (AA) to form epoxyeicosatrienoic acids (EETs), which exert beneficial roles in the treatment of cardiovascular diseases, but little is known about its role on adventitial remodeling. METHODS: We used C57BL/6J mice in vivo and primary rat adventitial fibroblasts (AFs) in vitro treated with Angiotensin II to investigate the effects of CYP2J2 gene delivery and exogenous EETs administration on adventitial remodeling...
2016: Cellular Physiology and Biochemistry
https://www.readbyqxmd.com/read/27451096/epoxyeicosatrienoic-acids-and-20-hydroxyeicosatetraenoic-acid-on-endothelial-and-vascular-function
#13
J D Imig
Endothelial and vascular smooth cells generate cytochrome P450 (CYP) arachidonic acid metabolites that can impact endothelial cell function and vascular homeostasis. The objective of this review is to focus on the physiology and pharmacology of endothelial CYP metabolites. The CYP pathway produces two types of eicosanoid products: epoxyeicosatrienoic acids (EETs), formed by CYP epoxygenases, and hydroxyeicosatetraenoic acids (HETEs), formed by CYP hydroxylases. Advances in CYP enzymes, EETs, and 20-HETE by pharmacological and genetic means have led to a more complete understanding of how these eicosanoids impact on endothelial cell function...
2016: Advances in Pharmacology
https://www.readbyqxmd.com/read/27448715/epoxyeicosatrienoic-acids-and-glucose-homeostasis-in-mice-and-men
#14
James M Luther, Nancy J Brown
Epoxyeicosatrienoic acids (EETs) are formed from arachidonic acid by the action of P450 epoxygenases (CYP2C and CYP2J). Effects of EETs are limited by hydrolysis by soluble epoxide hydrolase to less active dihydroxyeicosatrienoic acids. Studies in rodent models provide compelling evidence that epoxyeicosatrienoic acids exert favorable effects on glucose homeostasis, either by enhancing pancreatic islet cell function or by increasing insulin sensitivity in peripheral tissues. Specifically, the tissue expression of soluble epoxide hydrolase appears to be increased in rodent models of obesity and diabetes...
September 2016: Prostaglandins & Other Lipid Mediators
https://www.readbyqxmd.com/read/27401401/characterization-of-the-cytochrome-p450-epoxyeicosanoid-pathway-in-non-alcoholic-steatohepatitis
#15
Michael A Wells, Kimberly C Vendrov, Matthew L Edin, Brian C Ferslew, Weibin Zha, Bobbie K H Nguyen, Rachel J Church, Fred B Lih, Laura M DeGraff, Kim L R Brouwer, A Sidney Barritt, Darryl C Zeldin, Craig R Lee
Non-alcoholic steatohepatitis (NASH) is an emerging public health problem without effective therapies. Cytochrome P450 (CYP) epoxygenases metabolize arachidonic acid into bioactive epoxyeicosatrienoic acids (EETs), which have potent anti-inflammatory and protective effects. However, the functional relevance of the CYP epoxyeicosanoid metabolism pathway in the pathogenesis of NASH remains poorly understood. Our studies demonstrate that both mice with methionine-choline deficient (MCD) diet-induced NASH and humans with biopsy-confirmed NASH exhibited significantly higher free EET concentrations compared to healthy controls...
September 2016: Prostaglandins & Other Lipid Mediators
https://www.readbyqxmd.com/read/27358055/the-epoxyeicosatrienoic-acid-analog-pvpa-ameliorates-cyclosporine-induced-hypertension-and-renal-injury-in-rats
#16
Michael M Yeboah, Md Abdul Hye Khan, Marla A Chesnik, Amit Sharma, Mahesh P Paudyal, John R Falck, John D Imig
The introduction of calcineurin inhibitors (CNI) into clinical practice in the late 1970s transformed organ transplantation and led to significant improvement in acute rejection episodes. However, despite their significant clinical utility, the use of these agents is hampered by the development of hypertension and nephrotoxicity, which ultimately lead to end-stage kidney disease and overt cardiovascular outcomes. There are currently no effective agents to treat or prevent these complications. Importantly, CNI-free immunosuppressive regimens lack the overall efficacy of CNI-based treatments and put patients at risk of allograft rejection...
September 1, 2016: American Journal of Physiology. Renal Physiology
https://www.readbyqxmd.com/read/27354356/eets-and-ho-1-cross-talk
#17
REVIEW
David Sacerdoti, Paola Pesce, Marco Di Pascoli, Massimo Bolognesi
Epoxygenase-dependent metabolites of arachidonc acid, EETs and the heme-oxygenase (HO)-1/carbon monoxide/bilverdin system share similarities in their activity and mediators. They control endothelial function, dilating small arterial vessels, decrease blood pressure, protect the heart from ischemic and hypertensive cardiopathy, control renal circulation and function, promote angiogenesis and organ regeneration, oppose oxidative stress and inflammation, improve diabetes and obesity, have protective effects on the liver, and participate in portal hypertension...
September 2016: Prostaglandins & Other Lipid Mediators
https://www.readbyqxmd.com/read/27312119/inhibition-of-epoxyeicosatrienoic-acid-production-in-rats-with-cirrhosis-has-beneficial-effects-on-portal-hypertension-by-reducing-splanchnic-vasodilation
#18
Marco Di Pascoli, Francesca Zampieri, Alberto Verardo, Paola Pesce, Cristian Turato, Paolo Angeli, David Sacerdoti, Massimo Bolognesi
UNLABELLED: In cirrhosis, 11,12-epoxyeicosatrienoic acid (EET) induces mesenteric arterial vasodilation, which contributes to the onset of portal hypertension. We evaluated the hemodynamic effects of in vivo inhibition of EET production in experimental cirrhosis. Sixteen control rats and 16 rats with carbon tetrachloride-induced cirrhosis were studied. Eight controls and eight rats with cirrhosis were treated with the specific epoxygenase inhibitor N-(methylsulfonyl)-2-(2-propynyloxy)-benzenehexanamide (MS-PPOH; 20 mg/kg/day) for 3 consecutive days...
September 2016: Hepatology: Official Journal of the American Association for the Study of Liver Diseases
https://www.readbyqxmd.com/read/27286171/cyp2j2-regulation-function-and-polymorphism
#19
Michael Murray
Polyunsaturated fatty acids (PUFAs) undergo cytochrome P450 (CYP)-dependent oxidation to epoxides that modulate important physiological functions, including vasoactivity, inflammation, nociception, proliferation and viability. One of the most important human CYP epoxygenases is human CYP2J2 that is widely expressed in tissues, especially heart, vascular smooth muscle, salivary glands and placenta. Recent studies have shown that overexpression of CYP2J2 in vivo reverses several pathological processes in animals, including hypertension and other cardiovascular pathologies and insulin resistance...
August 2016: Drug Metabolism Reviews
https://www.readbyqxmd.com/read/27246851/characterization-of-eicosanoids-produced-by-adipocyte-lipolysis-implication-of-cyclooxygenase-2-in-adipose-inflammation
#20
Allison Gartung, Jiawei Zhao, Simon Chen, Emilio Mottillo, Garrett C VanHecke, Young-Hoon Ahn, Krishna Rao Maddipati, Andrey Sorokin, James Granneman, Menq-Jer Lee
Excessive adipocyte lipolysis generates lipid mediators and triggers inflammation in adipose tissue. However, the specific roles of lipolysis-generated mediators in adipose inflammation remain to be elucidated. In the present study, cultured 3T3-L1 adipocytes were treated with isoproterenol to activate lipolysis and the fatty acyl lipidome of released lipids was determined by using LC-MS/MS. We observed that β-adrenergic activation elevated levels of approximately fifty lipid species, including metabolites of cyclooxygenases, lipoxygenases, epoxygenases, and other sources...
July 29, 2016: Journal of Biological Chemistry
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