14R,15S-EpETrE (BioDeep_00001874883)

   


代谢物信息卡片


14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid

化学式: C20H32O3 (320.23513219999995)
中文名称: 14(S),15(R)-环氧-(5Z,8Z,11Z)-二十碳三烯酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC1C(O1)CC=CCC=CCC=CCCCC(=O)O
InChI: InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1

描述信息

D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

同义名列表

2 个代谢物同义名

14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid; 14R,15S-EpETrE



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Jie Zhang, Chuang Yang, Hongmei Qiu, Junxia Yang, Ke Wu, Shumei Ding, Chengyan Jiang, Qingsong Jiang. 14,15-EET involved in the development of diabetic cardiac hypertrophy mediated by PPARs. Prostaglandins & other lipid mediators. 2022 04; 159(?):106620. doi: 10.1016/j.prostaglandins.2022.106620. [PMID: 35091081]
  • Shanthi Nagarajan, Zu Yuan Qian, Parthiban Marimuthu, Nabil J Alkayed, Sanjiv Kaul, Anthony P Barnes. Mapping the Molecular Architecture Required for Lipid-Binding Pockets Using a Subset of Established and Orphan G-Protein Coupled Receptors. Journal of chemical information and modeling. 2021 07; 61(7):3442-3452. doi: 10.1021/acs.jcim.1c00335. [PMID: 34242503]
  • Menglu Fu, Jing Yu, Zhihui Chen, Ying Tang, Ruolan Dong, Yan Yang, Jinlan Luo, Shuiqing Hu, Ling Tu, Xizhen Xu. Epoxyeicosatrienoic acids improve glucose homeostasis by preventing NF-κB-mediated transcription of SGLT2 in renal tubular epithelial cells. Molecular and cellular endocrinology. 2021 03; 523(?):111149. doi: 10.1016/j.mce.2020.111149. [PMID: 33387601]
  • John D Imig, Wojciech K Jankiewicz, Abdul H Khan. Epoxy Fatty Acids: From Salt Regulation to Kidney and Cardiovascular Therapeutics: 2019 Lewis K. Dahl Memorial Lecture. Hypertension (Dallas, Tex. : 1979). 2020 07; 76(1):3-15. doi: 10.1161/hypertensionaha.120.13898. [PMID: 32475311]
  • Ming-Xiao Wang, Li-Jun Wang, Yu Xiao, Dan-Dan Zhang, Xin-Peng Duan, Wen-Hui Wang. Epoxyeicosatrienoic acid metabolites inhibit Kir4.1/Kir5.1 in the distal convoluted tubule. American journal of physiology. Renal physiology. 2020 06; 318(6):F1369-F1376. doi: 10.1152/ajprenal.00018.2020. [PMID: 32308018]
  • Mercè Pallàs, Santiago Vázquez, Coral Sanfeliu, Carles Galdeano, Christian Griñán-Ferré. Soluble Epoxide Hydrolase Inhibition to Face Neuroinflammation in Parkinson's Disease: A New Therapeutic Strategy. Biomolecules. 2020 05; 10(5):. doi: 10.3390/biom10050703. [PMID: 32369955]
  • Yi-Min Kuo, Pei-Chien Hsu, Chia-Chi Hung, Ya-Yu Hu, Yu-Jie Huang, Yu-Ling Gan, Chun-Hua Lin, Feng-Shiun Shie, Wen-Kuei Chang, Lung-Sen Kao, Mei-Yung Tsou, Yi-Hsuan Lee. Soluble Epoxide Hydrolase Inhibition Attenuates Excitotoxicity Involving 14,15-Epoxyeicosatrienoic Acid-Mediated Astrocytic Survival and Plasticity to Preserve Glutamate Homeostasis. Molecular neurobiology. 2019 Dec; 56(12):8451-8474. doi: 10.1007/s12035-019-01669-8. [PMID: 31257558]
  • Uwe Hoff, Gordana Bubalo, Mandy Fechner, Maximilian Blum, Ye Zhu, Andreas Pohlmann, Jan Hentschel, Karen Arakelyan, Erdmann Seeliger, Bert Flemming, Dennis Gürgen, Michael Rothe, Thoralf Niendorf, Vijaya L Manthati, John R Falck, Michael Haase, Wolf-Hagen Schunck, Duska Dragun. A synthetic epoxyeicosatrienoic acid analogue prevents the initiation of ischemic acute kidney injury. Acta physiologica (Oxford, England). 2019 10; 227(2):e13297. doi: 10.1111/apha.13297. [PMID: 31077555]
  • Maxwell Zeigler, Dale Whittington, Nona Sotoodehnia, Rozenn N Lemaitre, Rheem A Totah. A sensitive and improved throughput UPLC-MS/MS quantitation method of total cytochrome P450 mediated arachidonic acid metabolites that can separate regio-isomers and cis/trans-EETs from human plasma. Chemistry and physics of lipids. 2018 11; 216(?):162-170. doi: 10.1016/j.chemphyslip.2018.09.004. [PMID: 30201384]
  • Lu Liu, Nitin Puri, Marco Raffaele, Joseph Schragenheim, Shailendra P Singh, J Alyce Bradbury, Lars Bellner, Luca Vanella, Darryl C Zeldin, Jian Cao, Nader G Abraham. Ablation of soluble epoxide hydrolase reprogram white fat to beige-like fat through an increase in mitochondrial integrity, HO-1-adiponectin in vitro and in vivo. Prostaglandins & other lipid mediators. 2018 09; 138(?):1-8. doi: 10.1016/j.prostaglandins.2018.07.004. [PMID: 30041041]
  • Pinming Liu, Shaoling Zhang, Jingwei Gao, Ying Lin, Guangzi Shi, Wanbing He, Rhian M Touyz, Li Yan, Hui Huang. Downregulated Serum 14, 15-Epoxyeicosatrienoic Acid Is Associated With Abdominal Aortic Calcification in Patients With Primary Aldosteronism. Hypertension (Dallas, Tex. : 1979). 2018 04; 71(4):592-598. doi: 10.1161/hypertensionaha.117.10644. [PMID: 29440332]
  • Jing Luo, Jian-Feng Yao, Xiao-Fei Deng, Xiao-Dan Zheng, Min Jia, Yue-Qin Wang, Yan Huang, Jian-Hua Zhu. 14, 15-EET induces breast cancer cell EMT and cisplatin resistance by up-regulating integrin αvβ3 and activating FAK/PI3K/AKT signaling. Journal of experimental & clinical cancer research : CR. 2018 Feb; 37(1):23. doi: 10.1186/s13046-018-0694-6. [PMID: 29426357]
  • Qi Zhang, Xiang Wang, Guifang Yan, Juan Lei, Yu Zhou, Lei Wu, Ting Wang, Xiao Zhang, Duyun Ye, Yongsheng Li. Anti- Versus Pro-Inflammatory Metabololipidome Upon Cupping Treatment. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 45(4):1377-1389. doi: 10.1159/000487563. [PMID: 29462800]
  • 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. Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling. Proceedings of the National Academy of Sciences of the United States of America. 2017 11; 114(47):12608-12613. doi: 10.1073/pnas.1705615114. [PMID: 29109264]
  • Theresa Aliwarga, Brianne S Raccor, Rozenn N Lemaitre, Nona Sotoodehnia, Sina A Gharib, Libin Xu, Rheem A Totah. Enzymatic and free radical formation of cis- and trans- epoxyeicosatrienoic acids in vitro and in vivo. Free radical biology & medicine. 2017 11; 112(?):131-140. doi: 10.1016/j.freeradbiomed.2017.07.015. [PMID: 28734877]
  • William B Campbell, John D Imig, James M Schmitz, John R Falck. Orally Active Epoxyeicosatrienoic Acid Analogs. Journal of cardiovascular pharmacology. 2017 Oct; 70(4):211-224. doi: 10.1097/fjc.0000000000000523. [PMID: 28937442]
  • Julia M Santos, Jung-A Park, Aby Joiakim, David A Putt, Robert N Taylor, Hyesook Kim. The role of soluble epoxide hydrolase in preeclampsia. Medical hypotheses. 2017 Oct; 108(?):81-85. doi: 10.1016/j.mehy.2017.07.033. [PMID: 29055406]
  • Xuehong Liu, Zu-Yuan Qian, Fuchun Xie, Wei Fan, Jonathan W Nelson, Xiangshu Xiao, Sanjiv Kaul, Anthony P Barnes, Nabil J Alkayed. Functional screening for G protein-coupled receptor targets of 14,15-epoxyeicosatrienoic acid. Prostaglandins & other lipid mediators. 2017 09; 132(?):31-40. doi: 10.1016/j.prostaglandins.2016.09.002. [PMID: 27649858]
  • Yong Zhou, Tian Liu, Jia-Xi Duan, Ping Li, Guo-Ying Sun, Yong-Ping Liu, Jun Zhang, Liang Dong, Kin Sing Stephen Lee, Bruce D Hammock, Jian-Xin Jiang, Cha-Xiang Guan. Soluble Epoxide Hydrolase Inhibitor Attenuates Lipopolysaccharide-Induced Acute Lung Injury and Improves Survival in Mice. Shock (Augusta, Ga.). 2017 05; 47(5):638-645. doi: 10.1097/shk.0000000000000767. [PMID: 27753791]
  • Amy A Rand, Bogdan Barnych, Christophe Morisseau, Tomas Cajka, Kin Sing Stephen Lee, Dipak Panigrahy, Bruce D Hammock. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proceedings of the National Academy of Sciences of the United States of America. 2017 04; 114(17):4370-4375. doi: 10.1073/pnas.1616893114. [PMID: 28396419]
  • A Sporková, Z Husková, P Škaroupková, N Rami Reddy, J R Falck, J Sadowski, L Červenka. 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 failure. Physiological research. 2017 03; 66(1):29-39. doi: 10.33549/physiolres.933350. [PMID: 27782740]
  • Becca A Flitter, Kelli L Hvorecny, Emiko Ono, Taylor Eddens, Jun Yang, Daniel H Kwak, Christopher D Bahl, Thomas H Hampton, Christophe Morisseau, Bruce D Hammock, Xinyu Liu, Janet S Lee, Jay K Kolls, Bruce D Levy, Dean R Madden, Jennifer M Bomberger. Pseudomonas aeruginosa sabotages the generation of host proresolving lipid mediators. Proceedings of the National Academy of Sciences of the United States of America. 2017 01; 114(1):136-141. doi: 10.1073/pnas.1610242114. [PMID: 27980032]
  • Ingrid Fleming. The factor in EDHF: Cytochrome P450 derived lipid mediators and vascular signaling. Vascular pharmacology. 2016 11; 86(?):31-40. doi: 10.1016/j.vph.2016.03.001. [PMID: 26975734]
  • Alexandra Sporková, Rami N Reddy, John R Falck, John D Imig, Libor Kopkan, Janusz Sadowski, Luděk Červenka. Interlobular Arteries From 2-Kidney, 1-Clip Goldblatt Hypertensive Rats' Exhibit-Impaired Vasodilator Response to Epoxyeicosatrienoic Acids. The American journal of the medical sciences. 2016 05; 351(5):513-9. doi: 10.1016/j.amjms.2016.02.030. [PMID: 27140711]
  • Dorothee J Funk, Bernd L Sorg, Klaus Kopka, Heinz H Schmeiser. Epoxyeicosatrienoic acids (EETs) form adducts with DNA in vitro. Prostaglandins & other lipid mediators. 2016 03; 123(?):63-7. doi: 10.1016/j.prostaglandins.2016.04.006. [PMID: 27166927]
  • Haitham E El-Sikhry, Nasser Alsaleh, Rambabu Dakarapu, John R Falck, John M Seubert. Novel Roles of Epoxyeicosanoids in Regulating Cardiac Mitochondria. PloS one. 2016; 11(8):e0160380. doi: 10.1371/journal.pone.0160380. [PMID: 27494529]
  • Petra Alánová, Zuzana Husková, Libor Kopkan, Alexandra Sporková, Šárka Jíchová, Jan Neckář, John D Imig, Martina Klevstig, František Kolář, N Rami Reddy, John R Falck, Janusz Sadowski, Akira Nishiyama, Herbert J Kramer, Vojtěch Melenovský, Lenka Červenková, Petr Kujal, Zdenka Vernerová, Luděk Červenka. Orally active epoxyeicosatrienoic acid analog does not exhibit antihypertensive and reno- or cardioprotective actions in two-kidney, one-clip Goldblatt hypertensive rats. Vascular pharmacology. 2015 Oct; 73(?):45-56. doi: 10.1016/j.vph.2015.08.013. [PMID: 26304700]
  • Quan-Fei Zhu, Yan-Hong Hao, Ming-Zhou Liu, Jiang Yue, Jian Ni, Bi-Feng Yuan, Yu-Qi Feng. Analysis of cytochrome P450 metabolites of arachidonic acid by stable isotope probe labeling coupled with ultra high-performance liquid chromatography/mass spectrometry. Journal of chromatography. A. 2015 Sep; 1410(?):154-63. doi: 10.1016/j.chroma.2015.07.100. [PMID: 26253834]
  • Pulin Li, Jamie L Lahvic, Vera Binder, Emily K Pugach, Elizabeth B Riley, Owen J Tamplin, Dipak Panigrahy, Teresa V Bowman, Francesca G Barrett, Garrett C Heffner, Shannon McKinney-Freeman, Thorsten M Schlaeger, George Q Daley, Darryl C Zeldin, Leonard I Zon. Epoxyeicosatrienoic acids enhance embryonic haematopoiesis and adult marrow engraftment. Nature. 2015 Jul; 523(7561):468-71. doi: 10.1038/nature14569. [PMID: 26201599]
  • V Lamounier-Zepter, C Look, W-H Schunck, I Schlottmann, C Woischwill, S R Bornstein, A Xu, I Morano. Interaction of epoxyeicosatrienoic acids and adipocyte fatty acid-binding protein in the modulation of cardiomyocyte contractility. International journal of obesity (2005). 2015 May; 39(5):755-61. doi: 10.1038/ijo.2014.193. [PMID: 25370574]
  • Jiawen Xu, Christophe Morisseau, Jun Yang, Dadala M Mamatha, Bruce D Hammock. Epoxide hydrolase activities and epoxy fatty acids in the mosquito Culex quinquefasciatus. Insect biochemistry and molecular biology. 2015 Apr; 59(?):41-9. doi: 10.1016/j.ibmb.2015.02.004. [PMID: 25686802]
  • John D Imig. Epoxyeicosatrienoic acids, hypertension, and kidney injury. Hypertension (Dallas, Tex. : 1979). 2015 Mar; 65(3):476-82. doi: 10.1161/hypertensionaha.114.03585. [PMID: 25583156]
  • Guangzhi Chen, Renfan Xu, Shasha Zhang, Yinna Wang, Peihua Wang, Matthew L Edin, Darryl C Zeldin, Dao Wen Wang. CYP2J2 overexpression attenuates nonalcoholic fatty liver disease induced by high-fat diet in mice. American journal of physiology. Endocrinology and metabolism. 2015 Jan; 308(2):E97-E110. doi: 10.1152/ajpendo.00366.2014. [PMID: 25389366]
  • Ganggang Yu, Xiangjun Zeng, Hongxia Wang, Qi Hou, Chunting Tan, Qiufen Xu, Haoyan Wang. 14,15-epoxyeicosatrienoic Acid suppresses cigarette smoke extract-induced apoptosis in lung epithelial cells by inhibiting endoplasmic reticulum stress. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2015; 36(2):474-86. doi: 10.1159/000430113. [PMID: 25968975]
  • Lei Yang, Li Ni, Quanlu Duan, Xingxu Wang, Chen Chen, Song Chen, Sandip Chaugai, D C Zeldin, Jia Rong Tang, Dao Wen Wang. CYP epoxygenase 2J2 prevents cardiac fibrosis by suppression of transmission of pro-inflammation from cardiomyocytes to macrophages. Prostaglandins & other lipid mediators. 2015 Jan; 116-117(?):64-75. doi: 10.1016/j.prostaglandins.2015.01.004. [PMID: 25686540]
  • Tarvi Teder, William E Boeglin, Alan R Brash. Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction. Journal of lipid research. 2014 Dec; 55(12):2587-96. doi: 10.1194/jlr.m054072. [PMID: 25293588]
  • Cui Yang, Jinyan Yang, Xiangting Xu, Sanmei Yan, Shitian Pan, Xiaoxia Pan, Changhong Zhang, George Pakheng Leung. Vasodilatory effect of 14,15-epoxyeicosatrienoic acid on mesenteric arteries in hypertensive and aged rats. Prostaglandins & other lipid mediators. 2014 Aug; 112(?):1-8. doi: 10.1016/j.prostaglandins.2014.05.001. [PMID: 24880050]
  • Tian Yang, Ran Peng, Yuan Guo, Li Shen, Shuiping Zhao, Danyan Xu. The role of 14,15-dihydroxyeicosatrienoic acid levels in inflammation and its relationship to lipoproteins. Lipids in health and disease. 2013 Oct; 12(?):151. doi: 10.1186/1476-511x-12-151. [PMID: 24148690]
  • Patricia L Podolin, Brian J Bolognese, Joseph F Foley, Edward Long, Brian Peck, Sandra Umbrecht, Xiaojun Zhang, Penny Zhu, Benjamin Schwartz, Wensheng Xie, Chad Quinn, Hongwei Qi, Sharon Sweitzer, Stephanie Chen, Marc Galop, Yun Ding, Svetlana L Belyanskaya, David I Israel, Barry A Morgan, David J Behm, Joseph P Marino, Edit Kurali, Mary S Barnette, Ruth J Mayer, Catherine L Booth-Genthe, James F Callahan. In vitro and in vivo characterization of a novel soluble epoxide hydrolase inhibitor. Prostaglandins & other lipid mediators. 2013 Jul; 104-105(?):25-31. doi: 10.1016/j.prostaglandins.2013.02.001. [PMID: 23434473]
  • Ketul R Chaudhary, Beshay N M Zordoky, Matthew L Edin, Nasser Alsaleh, Ayman O S El-Kadi, Darryl C Zeldin, John M Seubert. Differential effects of soluble epoxide hydrolase inhibition and CYP2J2 overexpression on postischemic cardiac function in aged mice. Prostaglandins & other lipid mediators. 2013 Jul; 104-105(?):8-17. doi: 10.1016/j.prostaglandins.2012.08.001. [PMID: 22922020]
  • Lingdan Chen, Cheng Fan, Yi Zhang, Mahinur Bakri, Hua Dong, Christophe Morisseau, Krishna Rao Maddipati, Pengcheng Luo, Cong-Yi Wang, Bruce D Hammock, Mong-Heng Wang. Beneficial effects of inhibition of soluble epoxide hydrolase on glucose homeostasis and islet damage in a streptozotocin-induced diabetic mouse model. Prostaglandins & other lipid mediators. 2013 Jul; 104-105(?):42-8. doi: 10.1016/j.prostaglandins.2012.12.001. [PMID: 23247129]
  • Akinyemi Oni-Orisan, Yangmei Deng, Robert N Schuck, Katherine N Theken, Matthew L Edin, Fred B Lih, Kimberly Molnar, Laura DeGraff, Kenneth B Tomer, Darryl C Zeldin, Craig R Lee. Dual modulation of cyclooxygenase and CYP epoxygenase metabolism and acute vascular inflammation in mice. Prostaglandins & other lipid mediators. 2013 Jul; 104-105(?):67-73. doi: 10.1016/j.prostaglandins.2012.09.003. [PMID: 23000418]
  • Garrett J Gross, Anna Hsu, Adam W Pfeiffer, Kasem Nithipatikom. Roles of endothelial nitric oxide synthase (eNOS) and mitochondrial permeability transition pore (MPTP) in epoxyeicosatrienoic acid (EET)-induced cardioprotection against infarction in intact rat hearts. Journal of molecular and cellular cardiology. 2013 Jun; 59(?):20-9. doi: 10.1016/j.yjmcc.2013.02.003. [PMID: 23419451]
  • Nataliya Pidkovka, Reena Rao, Shaojun Mei, Yan Gong, Raymond C Harris, Wen-Hui Wang, Jorge H Capdevila. Epoxyeicosatrienoic acids (EETs) regulate epithelial sodium channel activity by extracellular signal-regulated kinase 1/2 (ERK1/2)-mediated phosphorylation. The Journal of biological chemistry. 2013 Feb; 288(7):5223-31. doi: 10.1074/jbc.m112.407981. [PMID: 23283969]
  • Stephanie Eid, Rita Maalouf, Ayad A Jaffa, Joseph Nassif, Ahmed Hamdy, Awad Rashid, Fuad N Ziyadeh, Assaad A Eid. 20-HETE and EETs in diabetic nephropathy: a novel mechanistic pathway. PloS one. 2013; 8(8):e70029. doi: 10.1371/journal.pone.0070029. [PMID: 23936373]
  • Rui Li, Xizhen Xu, Chen Chen, Xuefeng Yu, Matthew L Edin, Laura Miller Degraff, Craig R Lee, Darryl C Zeldin, Dao Wen Wang. Cytochrome P450 2J2 is protective against global cerebral ischemia in transgenic mice. Prostaglandins & other lipid mediators. 2012 Dec; 99(3-4):68-78. doi: 10.1016/j.prostaglandins.2012.09.004. [PMID: 23041291]
  • Martina Decker, Magdalena Adamska, Annette Cronin, Francesca Di Giallonardo, Julia Burgener, Anne Marowsky, John R Falck, Christophe Morisseau, Bruce D Hammock, Artiom Gruzdev, Darryl C Zeldin, Michael Arand. EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides. Journal of lipid research. 2012 Oct; 53(10):2038-2045. doi: 10.1194/jlr.m024448. [PMID: 22798687]
  • Katherine N Theken, Robert N Schuck, Matthew L Edin, Bryant Tran, Kyle Ellis, Almasa Bass, Fred B Lih, Kenneth B Tomer, Samuel M Poloyac, Michael C Wu, Alan L Hinderliter, Darryl C Zeldin, George A Stouffer, Craig R Lee. Evaluation of cytochrome P450-derived eicosanoids in humans with stable atherosclerotic cardiovascular disease. Atherosclerosis. 2012 Jun; 222(2):530-6. doi: 10.1016/j.atherosclerosis.2012.03.022. [PMID: 22503544]
  • Natalie C Ward, Kevin D Croft, David Blacker, Graeme J Hankey, Anne Barden, Trevor A Mori, Ian B Puddey, Christopher D Beer. Cytochrome P450 metabolites of arachidonic acid are elevated in stroke patients compared with healthy controls. Clinical science (London, England : 1979). 2011 Dec; 121(11):501-7. doi: 10.1042/cs20110215. [PMID: 21689071]
  • Kathryn M Gauthier, Lauren Olson, Adam Harder, Marilyn Isbell, John D Imig, David D Gutterman, J R Falck, William B Campbell. Soluble epoxide hydrolase contamination of specific catalase preparations inhibits epoxyeicosatrienoic acid vasodilation of rat renal arterioles. American journal of physiology. Renal physiology. 2011 Oct; 301(4):F765-72. doi: 10.1152/ajprenal.00201.2011. [PMID: 21753077]
  • Penny Zhu, Brian Peck, Hermes Licea-Perez, James F Callahan, Catherine Booth-Genthe. 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. 2011 Sep; 879(25):2487-93. doi: 10.1016/j.jchromb.2011.06.042. [PMID: 21798825]
  • Tengis S Pavlov, Daria V Ilatovskaya, Vladislav Levchenko, David L Mattson, Richard J Roman, Alexander Staruschenko. Effects of cytochrome P-450 metabolites of arachidonic acid on the epithelial sodium channel (ENaC). American journal of physiology. Renal physiology. 2011 Sep; 301(3):F672-81. doi: 10.1152/ajprenal.00597.2010. [PMID: 21697242]
  • Jill E Skepner, Lorraine D Shelly, Chengjie Ji, Benjamin Reidich, Yi Luo. Chronic treatment with epoxyeicosatrienoic acids modulates insulin signaling and prevents insulin resistance in hepatocytes. Prostaglandins & other lipid mediators. 2011 Feb; 94(1-2):3-8. doi: 10.1016/j.prostaglandins.2010.10.002. [PMID: 21040800]
  • Cui Yang, Yiu-Wa Kwan, Alice Lai-Shan Au, Christina Chui-Wa Poon, Qian Zhang, Shun-Wan Chan, Simon Ming-Yuen Lee, George Pak-Heng Leung. 14,15-Epoxyeicosatrienoic acid induces vasorelaxation through the prostaglandin EP(2) receptors in rat mesenteric artery. Prostaglandins & other lipid mediators. 2010 Sep; 93(1-2):44-51. doi: 10.1016/j.prostaglandins.2010.06.004. [PMID: 20601071]
  • Satoshi Imaizumi, Victor Grijalva, Mohamad Navab, Brian J Van Lenten, Alan C Wagner, G M Anantharamiah, Alan M Fogelman, Srinivasa T Reddy. L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice. Drug metabolism letters. 2010 Aug; 4(3):139-48. doi: 10.2174/187231210791698438. [PMID: 20642447]
  • Helen E Smith, J P Jones, Thomas F Kalhorn, Federico M Farin, Patricia L Stapleton, Connie L Davis, James D Perkins, David K Blough, Mary F Hebert, Kenneth E Thummel, Rheem A Totah. Role of cytochrome P450 2C8 and 2J2 genotypes in calcineurin inhibitor-induced chronic kidney disease. Pharmacogenetics and genomics. 2008 Nov; 18(11):943-53. doi: 10.1097/fpc.0b013e32830e1e16. [PMID: 18769365]
  • Sarbani Ghosh, Po-Chang Chiang, Jan L Wahlstrom, Hideji Fujiwara, Jon G Selbo, Steven L Roberds. Oral delivery of 1,3-dicyclohexylurea nanosuspension enhances exposure and lowers blood pressure in hypertensive rats. Basic & clinical pharmacology & toxicology. 2008 May; 102(5):453-8. doi: 10.1111/j.1742-7843.2008.00213.x. [PMID: 18312493]
  • Jianchun Chen, Jian-Kang Chen, John R Falck, Jagadeesh Setti Guthi, Siddam Anjaiah, Jorge H Capdevila, Raymond C Harris. Mitogenic activity and signaling mechanism of 2-(14,15- epoxyeicosatrienoyl)glycerol, a novel cytochrome p450 arachidonate metabolite. Molecular and cellular biology. 2007 Apr; 27(8):3023-34. doi: 10.1128/mcb.01482-06. [PMID: 17283047]
  • Caroline Morin, Eric Rousseau. Effects of 5-oxo-ETE and 14,15-EET on reactivity and Ca2+ sensitivity in guinea pig bronchi. Prostaglandins & other lipid mediators. 2007 Jan; 82(1-4):30-41. doi: 10.1016/j.prostaglandins.2006.05.012. [PMID: 17164130]
  • Jian Gang Jiang, Rui Juan Chen, Bin Xiao, Shilin Yang, Jia Ning Wang, Yong Wang, L Ashley Cowart, Xiao Xiao, Dao Wen Wang, Yong Xia. Regulation of endothelial nitric-oxide synthase activity through phosphorylation in response to epoxyeicosatrienoic acids. Prostaglandins & other lipid mediators. 2007 Jan; 82(1-4):162-74. doi: 10.1016/j.prostaglandins.2006.08.005. [PMID: 17164144]
  • Xiang Fang, Shanming Hu, Bingkun Xu, Gary D Snyder, Shawn Harmon, Jianrong Yao, Yi Liu, Bhavani Sangras, J R Falck, Neal L Weintraub, Arthur A Spector. 14,15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-alpha. American journal of physiology. Heart and circulatory physiology. 2006 Jan; 290(1):H55-63. doi: 10.1152/ajpheart.00427.2005. [PMID: 16113065]
  • Xiang Fang, Shanming Hu, Takaho Watanabe, Neal L Weintraub, Gary D Snyder, Jianrong Yao, Yi Liu, John Y-J Shyy, Bruce D Hammock, Arthur A Spector. Activation of peroxisome proliferator-activated receptor alpha by substituted urea-derived soluble epoxide hydrolase inhibitors. The Journal of pharmacology and experimental therapeutics. 2005 Jul; 314(1):260-70. doi: 10.1124/jpet.105.085605. [PMID: 15798002]
  • Xiang Fang, Neal L Weintraub, Ryan B McCaw, Shanming Hu, Shawn D Harmon, James B Rice, Bruce D Hammock, Arthur A Spector. Effect of soluble epoxide hydrolase inhibition on epoxyeicosatrienoic acid metabolism in human blood vessels. American journal of physiology. Heart and circulatory physiology. 2004 Dec; 287(6):H2412-20. doi: 10.1152/ajpheart.00527.2004. [PMID: 15284062]
  • Motoaki Miyazono, Daling Zhu, Raphael Nemenoff, Elizabeth R Jacobs, Ethan P Carter. Increased epoxyeicosatrienoic acid formation in the rat kidney during liver cirrhosis. Journal of the American Society of Nephrology : JASN. 2003 Jul; 14(7):1766-75. doi: 10.1097/01.asn.0000076074.63334.99. [PMID: 12819236]
  • Dan Wang, Lillian J Borrego-Conde, John R Falck, Kamalesh K Sharma, Christopher S Wilcox, Jason G Umans. Contributions of nitric oxide, EDHF, and EETs to endothelium-dependent relaxation in renal afferent arterioles. Kidney international. 2003 Jun; 63(6):2187-93. doi: 10.1046/j.1523-1755.2003.00036.x. [PMID: 12753306]
  • Xiang Fang, Neal L Weintraub, Arthur A Spector. Differences in positional esterification of 14,15-epoxyeicosatrienoic acid in phosphatidylcholine of porcine coronary artery endothelial and smooth muscle cells. Prostaglandins & other lipid mediators. 2003 Apr; 71(1-2):33-42. doi: 10.1016/s0090-6980(03)00002-9. [PMID: 12749592]
  • Gary D Snyder, U Murali Krishna, J R Falck, Arthur A Spector. 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. 2002 Nov; 283(5):H1936-42. doi: 10.1152/ajpheart.00321.2002. [PMID: 12384472]
  • Kathryn M Gauthier, Christina Deeter, U Murali Krishna, Y Krishna Reddy, Muralidhar Bondlela, J R Falck, William B Campbell. 14,15-Epoxyeicosa-5(Z)-enoic acid: a selective epoxyeicosatrienoic acid antagonist that inhibits endothelium-dependent hyperpolarization and relaxation in coronary arteries. Circulation research. 2002 May; 90(9):1028-36. doi: 10.1161/01.res.0000018162.87285.f8. [PMID: 12016270]
  • Dany Salvail, Martin Cloutier, Eric Rousseau. Functional reconstitution of an eicosanoid-modulated Cl- channel from bovine tracheal smooth muscle. American journal of physiology. Cell physiology. 2002 Mar; 282(3):C567-77. doi: 10.1152/ajpcell.00029.2001. [PMID: 11832342]
  • X Fang, T L Kaduce, N L Weintraub, S Harmon, L M Teesch, C Morisseau, D A Thompson, B D Hammock, A A Spector. Pathways of epoxyeicosatrienoic acid metabolism in endothelial cells. Implications for the vascular effects of soluble epoxide hydrolase inhibition. The Journal of biological chemistry. 2001 May; 276(18):14867-74. doi: 10.1074/jbc.m011761200. [PMID: 11278979]
  • J D Imig, X Zhao, J R Falck, S Wei, J H Capdevila. Enhanced renal microvascular reactivity to angiotensin II in hypertension is ameliorated by the sulfonimide analog of 11,12-epoxyeicosatrienoic acid. Journal of hypertension. 2001 May; 19(5):983-92. doi: 10.1097/00004872-200105000-00020. [PMID: 11393683]
  • K Nithipatikom, R F DiCamelli, S Kohler, R J Gumina, J R Falck, W B Campbell, G J Gross. Determination of cytochrome P450 metabolites of arachidonic acid in coronary venous plasma during ischemia and reperfusion in dogs. Analytical biochemistry. 2001 May; 292(1):115-24. doi: 10.1006/abio.2001.5044. [PMID: 11319825]
  • M Medhora, J Narayanan, D Harder. Dual regulation of the cerebral microvasculature by epoxyeicosatrienoic acids. Trends in cardiovascular medicine. 2001 Jan; 11(1):38-42. doi: 10.1016/s1050-1738(01)00082-2. [PMID: 11413051]
  • Z Yu, F Xu, L M Huse, C Morisseau, A J Draper, J W Newman, C Parker, L Graham, M M Engler, B D Hammock, D C Zeldin, D L Kroetz. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circulation research. 2000 Nov; 87(11):992-8. doi: 10.1161/01.res.87.11.992. [PMID: 11090543]
  • P Y Wong, P S Lai, J R Falck. Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytes. Prostaglandins & other lipid mediators. 2000 Oct; 62(4):321-33. doi: 10.1016/s0090-6980(00)00079-4. [PMID: 11060896]
  • J K Chen, J Capdevila, R C Harris. Overexpression of C-terminal Src kinase blocks 14, 15-epoxyeicosatrienoic acid-induced tyrosine phosphorylation and mitogenesis. The Journal of biological chemistry. 2000 May; 275(18):13789-92. doi: 10.1074/jbc.275.18.13789. [PMID: 10788500]
  • Z Yu, L M Huse, P Adler, L Graham, J Ma, D C Zeldin, D L Kroetz. Increased CYP2J expression and epoxyeicosatrienoic acid formation in spontaneously hypertensive rat kidney. Molecular pharmacology. 2000 May; 57(5):1011-20. doi: . [PMID: 10779386]
  • N L Weintraub, X Fang, T L Kaduce, M VanRollins, P Chatterjee, A A Spector. Epoxide hydrolases regulate epoxyeicosatrienoic acid incorporation into coronary endothelial phospholipids. The American journal of physiology. 1999 11; 277(5):H2098-108. doi: 10.1152/ajpheart.1999.277.5.h2098. [PMID: 10564166]
  • D M Silverstein, M Barac-Nieto, A Spitzer. Multiple arachidonic acid metabolites inhibit sodium-dependent phosphate transport in OK cells. Prostaglandins, leukotrienes, and essential fatty acids. 1999 Sep; 61(3):165-9. doi: 10.1054/plef.1999.0086. [PMID: 10582656]
  • S Huang, M Konieczkowski, J R Schelling, J R Sedor. Interleukin-1 stimulates Jun N-terminal/stress-activated protein kinase by an arachidonate-dependent mechanism in mesangial cells. Kidney international. 1999 May; 55(5):1740-9. doi: 10.1046/j.1523-1755.1999.00440.x. [PMID: 10231436]
  • P Y Wong, P S Lai, S Y Shen, Y Y Belosludtsev, J R Falck. Post-receptor signal transduction and regulation of 14(R),15(S)-epoxyeicosatrienoic acid (14,15-EET) binding in U-937 cells. Journal of lipid mediators and cell signalling. 1997 Jul; 16(3):155-69. doi: 10.1016/s0929-7855(97)00005-9. [PMID: 9246605]
  • A Zosmer, N B Rendell, G W Taylor, M G Elder, M H Sullivan. Formation and metabolism of 14,15-epoxyeicosatrienoic acid by human reproductive tissues. Biochimica et biophysica acta. 1995 Oct; 1258(3):234-40. doi: 10.1016/0005-2760(95)00120-2. [PMID: 7548192]
  • M VanRollins, P M Kochanek, R W Evans, J K Schiding, E M Nemoto. Optimization of epoxyeicosatrienoic acid syntheses to test their effects on cerebral blood flow in vivo. Biochimica et biophysica acta. 1995 Jun; 1256(3):263-74. doi: 10.1016/0005-2760(95)00029-c. [PMID: 7786887]
  • X Fang, M VanRollins, T L Kaduce, A A Spector. Epoxyeicosatrienoic acid metabolism in arterial smooth muscle cells. Journal of lipid research. 1995 Jun; 36(6):1236-46. doi: 10.1016/s0022-2275(20)41131-9. [PMID: 7666001]
  • B A Escalante, R Staudinger, M Schwartzman, N Abraham. Amiloride-sensitive ion transport inhibition by epoxyeicosatrienoic acids in renal epithelial cells. Advances in prostaglandin, thromboxane, and leukotriene research. 1995; 23(?):207-9. doi: NULL. [PMID: 7732836]
  • B E Daikh, J M Lasker, J L Raucy, D R Koop. Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9. The Journal of pharmacology and experimental therapeutics. 1994 Dec; 271(3):1427-33. doi: . [PMID: 7996455]
  • Y H Ma, M L Schwartzman, R J Roman. Altered renal P-450 metabolism of arachidonic acid in Dahl salt-sensitive rats. The American journal of physiology. 1994 Aug; 267(2 Pt 2):R579-89. doi: 10.1152/ajpregu.1994.267.2.r579. [PMID: 8067471]
  • R Staudinger, B Escalante, M L Schwartzman, N G Abraham. Effects of epoxyeicosatrienoic acids on 86Rb uptake in renal epithelial cells. Journal of cellular physiology. 1994 Jul; 160(1):69-74. doi: 10.1002/jcp.1041600109. [PMID: 8021300]
  • J D Imig, A P Zou, P R Ortiz de Montellano, Z Sui, R J Roman. Cytochrome P-450 inhibitors alter afferent arteriolar responses to elevations in pressure. The American journal of physiology. 1994 May; 266(5 Pt 2):H1879-85. doi: 10.1152/ajpheart.1994.266.5.h1879. [PMID: 8203587]
  • P Y Wong, K T Lin, Y T Yan, D Ahern, J Iles, S Y Shen, R K Bhatt, J R Falck. 14(R),15(S)-epoxyeicosatrienoic acid (14(R),15(S)-EET) receptor in guinea pig mononuclear cell membranes. Journal of lipid mediators. 1993 Mar; 6(1-3):199-208. doi: . [PMID: 8395243]
  • A Karara, S Wei, D Spady, L Swift, J H Capdevila, J R Falck. Arachidonic acid epoxygenase: structural characterization and quantification of epoxyeicosatrienoates in plasma. Biochemical and biophysical research communications. 1992 Feb; 182(3):1320-5. doi: 10.1016/0006-291x(92)91877-s. [PMID: 1540175]
  • M A Carroll, M P Garcia, J R Falck, J C McGiff. Cyclooxygenase dependency of the renovascular actions of cytochrome P450-derived arachidonate metabolites. The Journal of pharmacology and experimental therapeutics. 1992 Jan; 260(1):104-9. doi: . [PMID: 1731035]
  • M L Heizer, J S McKinney, E F Ellis. 14,15-Epoxyeicosatrienoic acid inhibits platelet aggregation in mouse cerebral arterioles. Stroke. 1991 Nov; 22(11):1389-93. doi: 10.1161/01.str.22.11.1389. [PMID: 1750047]
  • T Force, G Hyman, R Hajjar, A Sellmayer, J V Bonventre. Noncyclooxygenase metabolites of arachidonic acid amplify the vasopressin-induced Ca2+ signal in glomerular mesangial cells by releasing Ca2+ from intracellular stores. The Journal of biological chemistry. 1991 Mar; 266(7):4295-302. doi: . [PMID: 1900289]
  • F Catella, J Lawson, G Braden, D J Fitzgerald, E Shipp, G A FitzGerald. Biosynthesis of P450 products of arachidonic acid in humans: increased formation in cardiovascular disease. Advances in prostaglandin, thromboxane, and leukotriene research. 1991; 21A(?):193-6. doi: NULL. [PMID: 1705382]
  • F Catella, J A Lawson, D J Fitzgerald, G A FitzGerald. Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension. Proceedings of the National Academy of Sciences of the United States of America. 1990 Aug; 87(15):5893-7. doi: 10.1073/pnas.87.15.5893. [PMID: 2198572]
  • A Karara, E Dishman, H Jacobson, J R Falck, J H Capdevila. Arachidonic acid epoxygenase. Stereochemical analysis of the endogenous epoxyeicosatrienoic acids of human kidney cortex. FEBS letters. 1990 Jul; 268(1):227-30. doi: 10.1016/0014-5793(90)81014-f. [PMID: 2384159]
  • W K Lin, J R Falck, P Y Wong. Effect of 14,15-epoxyeicosatrienoic acid infusion on blood pressure in normal and hypertensive rats. Biochemical and biophysical research communications. 1990 Mar; 167(3):977-81. doi: 10.1016/0006-291x(90)90619-x. [PMID: 2322287]
  • G A Ulsaker, G Teien. Gas chromatographic-mass spectrometric identification of four triene monoepoxides of arachidonic acid in human plasma. The Analyst. 1990 Mar; 115(3):259-62. doi: 10.1039/an9901500259. [PMID: 2327589]