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Dihydroxy-Metabolites of Dihomo-γ-linolenic Acid Drive Ferroptosis-Mediated Neurodegeneration has been published in ACS Central Science, March 2023, Congrats Morteza!!
The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms. Prostaglandins Other Lipid Mediat. 2022 Oct;162:106662. doi: 10.1016/j.prostaglandins.2022.106662. Epub 2022 Jun 30. PubMed PMID: 35779854; PubMed Central PMCID: PMC9530012.
Relative Importance of Soluble and Microsomal Epoxide Hydrolases for the Hydrolysis
of Epoxy-Fatty Acids in Human Tissues. Int J Mol Sci. 2021 May 8;22(9). doi: 10.3390/ijms22094993. PubMed PMID: 34066758; PubMed Central PMCID: PMC8125816.
Target-Mediated Drug Disposition-A Class Effect of Soluble Epoxide Hydrolase Inhibitors. J Clin Pharmacol. 2021 Apr;61(4):531-537. doi: 10.1002/jcph.1763. Epub 2020 Oct 19. Review. PubMed PMID: 33078430; PubMed Central PMCID: PMC7969377.
Movement to the Clinic of Soluble Epoxide Hydrolase Inhibitor EC5026 as an Analgesic for Neuropathic Pain and for Use as a Nonaddictive Opioid Alternative. J Med Chem. 2021 Feb 25;64(4):1856-1872. doi: 10.1021/acs.jmedchem.0c01886. Epub 2021 Feb 7. PubMed PMID: 33550801; PubMed Central PMCID: PMC7917437.
Target-Mediated Drug Disposition (TMDD) – a Class Effect of Soluble Epoxide Hydrolase (sEH) Inhibitors Guohua An MD, PhD, Kin Sing Stephen Lee PhD, Jun Yang PhD, Bruce D. Hammock PhD. The Journal of Clinical Pharmacology, 19 October 2020.
Cytochrome P450 Metabolism of Polyunsaturated Fatty Acids and Neurodegeneration. Nutrients. 2020 Nov 16;12(11). doi: 10.3390/nu12113523. Review. PubMed PMID: 33207662; PubMed Central PMCID: PMC7696575.
Preparation and evaluation of soluble epoxide hydrolase inhibitors with improved physical properties and potencies for treating diabetic neuropathic pain. Bioorg Med Chem. 2020 Nov 15;28(22):115735. doi: 10.1016/j.bmc.2020.115735. Epub 2020 Aug 31. PubMed PMID: 33007552; PubMed Central PMCID: PMC7914304.
Suppression of inflammation and fibrosis using soluble epoxide hydrolase inhibitors enhances cardiac stem cell-based therapy. Stem Cells Transl Med. 2020 Dec;9(12):1570-1584. doi: 10.1002/sctm.20-0143. Epub 2020 Aug 13. PubMed PMID: 32790136; PubMed Central PMCID: PMC7695637.
Simultaneous Target-Mediated Drug Disposition (TMDD) Model for Two Small-Molecule Compounds Competing for Their Pharmacological Target: Soluble Epoxide Hydrolase Nan Wu, Bruce Hammock, Kin Sing Stephen Lee and Guohua An. Journal of Pharmacology and Experimental Therapeutics April 1, 2020, jpet.120.265330
Soluble epoxide hydrolase is an endogenous regulator of obesity-induced intestinal barrier dysfunction and bacterial translocation. Proc Natl Acad Sci U S A. 2020 Apr 14;117(15):8431-8436. doi: 10.1073/pnas.1916189117. Epub 2020 Mar 27. PubMed PMID: 32220957; PubMed Central PMCID: PMC7165420.
Selection of Potent Inhibitors of Soluble Epoxide Hydrolase for Usage in Veterinary Medicine. Front Vet Sci. 2020;7:580. doi: 10.3389/fvets.2020.00580. eCollection 2020. PubMed PMID: 33005645; PubMed Central PMCID: PMC7479175.
Inactivation of Cys 674 in SERCA2 increases BP by inducing endoplasmic reticulum stress and soluble epoxide hydrolase British Journal of Pharmacology 2020-01-30.
Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid Maris A Cinelli, Kin Sing Stephen Lee The Journal of Organic Chemistry 2019-12-06
trans, trans-2,4-Decadienal, a lipid peroxidation product, induces inflammatory responses via Hsp90- or 14-3-3ζ-dependent mechanisms Yuxin Wang, Devon A Dattmore, Weicang Wang, Georg Pohnert, Stefanie Wolfram, Jianan Zhang, Ran Yang, Eric A Decker, Kin Sing Stephen Lee, Guodong Zhang The Journal of Nutritional Biochemistry 2019
Drug-Target Residence Time Affects in Vivo Target Occupancy through Multiple Pathways Kin Sing Stephen Lee, Jun Yang, Jun Niu, Connie J. Ng, Karen M. Wagner, Hua Dong, Sean D. Kodani, Debin Wan, Christophe Morisseau, Bruce D. Hammock. ACS Cent. Sci.2019591614-1624, September 3, 2019
*For those who are interested in the data in this manuscript, please contact sing@msu.edu
Woodman, J. W., Cinelli, M. A., Scharmen-Burgdolf, A., Lee, K. S. J. Vis. Exp. (148), e59770, doi:10.3791/59770 (2019). PDF
Drug-Target Residence Time Affects in Vivo Target Occupancy through Multiple Pathways Kin Sing Stephen Lee, Jun Yan Jun Niu Connie J. Ng Karen M. Wagner Hua Dong Sean D. Kodani Debin Wan Christophe Morisseau Bruce D. Hammock, ACS Cent. Sci. (2019).
Targeted Metabolomics Identifies the Cytochrome P450 Monooxygenase Eicosanoid Pathway as a Novel Therapeutic Target of Colon Tumorigenesis. Cancer Res. 2019 Apr 15;79(8):1822-1830. doi: 10.1158/0008-5472.CAN-18-3221. Epub 2019 Feb 25.
Brain oxylipin concentrations following hypercapnia/ischemia: effects of brain dissection and dissection time. J Lipid Res. 2019 Mar;60(3):671-682. doi: 10.1194/jlr.D084228. Epub 2018 Nov 21.
Enzymatic synthesis and chemical inversion provide both enantiomers of bioactive epoxydocosapentaenoic acids Maris A. Cinelli, Jun Yang, Amy Scharmen, Joey Woodman, Lalitha M. Karchalla and Kin Sing Stephen Lee, The Journal of Lipid Research, 59, 2237-2252 (2018). PDF
Correction to Optimized Inhibitors of Soluble Epoxide Hydrolase Improve in Vitro Target Residence Time and in Vivo Efficacy. J Med Chem. 2018 May 10;61(9):4271. doi: 10.1021/acs.jmedchem.8b00582. Epub 2018 Apr 27.
Soluble epoxide hydrolase inhibition decreases reperfusion injury after focal cerebral ischemia. Sci Rep. 2018 Mar 27;8(1):5279. doi: 10.1038/s41598-018-23504-1.
A new sensitive LC/MS/MS analysis of vitamin D metabolites using a click derivatization reagent, 2-nitrosopyridine Debin Wan, Jun Yang, Bogdan Barnych, Sung Hee Hwang, Kin Sing Stephen Lee, Yongliang Cui, Jun Niu, Mitchell A Watsky, Bruce D Hammock J Lipid Res 2017
Chemical synthesis and biological evaluation of omega-hydroxy polyunsaturated fatty acids Sung Hee Hwang, Karen Wagner, Jian Xu, Jun Yang, Xichun Li, Zhengyu Cao, Christophe Morisseau, Kin Sing Stephen Lee, Bruce D Hammock Bioorg Med Chem Lett 2017
Epoxy fatty acids mediate analgesia in murine diabetic neuropathy K Wagner, K S S Lee, J Yang, B D Hammock Eur J Pain 2017
Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling. Proc Natl Acad Sci U S A. 2017 Nov 21;114(47):12608-12613. doi: 10.1073/pnas.1705615114. Epub 2017 Nov 6.
Cytochrome P450 monooxygenase lipid metabolites are significant second messengers in the resolution of choroidal neovascularization. Proc Natl Acad Sci U S A. 2017 Sep 5;114(36):E7545-E7553. doi: 10.1073/pnas.1620898114. Epub 2017 Aug 21.
Soluble epoxide hydrolase in podocytes is a significant contributor to renal function under hyperglycemia. Biochim Biophys Acta Gen Subj. 2017 Nov;1861(11 Pt A):2758-2765. doi: 10.1016/j.bbagen.2017.07.021. Epub 2017 Jul 27.
ω-3 Polyunsaturated fatty acids and their cytochrome P450-derived metabolites suppress colorectal tumor development in mice. J Nutr Biochem. 2017 Oct;48:29-35. doi: 10.1016/j.jnutbio.2017.06.006. Epub 2017 Jun 21.
Linoleic acid participates in the response to ischemic brain injury through oxidized metabolites that regulate neurotransmission. Sci Rep. 2017 Jun 28;7(1):4342. doi: 10.1038/s41598-017-02914-7.
Synthesis of cyclooxygenase metabolites of 8,9-epoxyeicosatrienoic acid (EET): 11- and 15-hydroxy 8,9-EETs. Org Biomol Chem. 2017 May 23;15(20):4308-4313. doi: 10.1039/c7ob00789b.
Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc Natl Acad Sci U S A. 2017 Apr 25;114(17):4370-4375. doi: 10.1073/pnas.1616893114. Epub 2017 Apr 10.
Active-Site Flexibility and Substrate Specificity in a Bacterial Virulence Factor: Crystallographic Snapshots of an Epoxide Hydrolase. Structure. 2017 May 2;25(5):697-707.e4. doi: 10.1016/j.str.2017.03.002. Epub 2017 Apr 6.
Soluble Epoxide Hydrolase Pharmacological Inhibition Decreases Alveolar Bone Loss by Modulating Host Inflammatory Response, RANK-Related Signaling, Endoplasmic Reticulum Stress, and Apoptosis. J Pharmacol Exp Ther. 2017 Jun;361(3):408-416. doi: 10.1124/jpet.116.238113. Epub 2017 Mar 29.
Endothelial Nox4-based NADPH oxidase regulates atherosclerosis via soluble epoxide hydrolase. Biochim Biophys Acta Mol Basis Dis. 2017 Jun;1863(6):1382-1391. doi: 10.1016/j.bbadis.2017.02.004. Epub 2017 Feb 7.
Soluble Epoxide Hydrolase Inhibitor Attenuates Lipopolysaccharide-Induced Acute Lung Injury and Improves Survival in Mice. Shock. 2017 May;47(5):638-645. doi: 10.1097/SHK.0000000000000767.
Inhibition of soluble epoxide hydrolase augments astrocyte release of vascular endothelial growth factor and neuronal recovery after oxygen-glucose deprivation Yue Zhang, Gina Hong, Kin Sing Stephen Lee, Bruce D Hammock, Debebe Gebremedhin, David R Harder, Raymond C Koehler, Adam Sapirstein J Neurochem 2017.
Probing the orientation of inhibitor and epoxy-eicosatrienoic acid binding in the active site of soluble epoxide hydrolase Kin Sing Stephen Lee 1, Niel M Henriksen 2, Connie J Ng 1, Jun Yang 1, Weitao Jia 3, Christophe Morisseau 1, Armann Andaya 3, Michael K Gilson 2, Bruce D Hammock 4 Arch Biochem Biophys 2017.
Cytochrome P450 Oxidase 2C Inhibition Adds to omega-3 Long-Chain Polyunsaturated Fatty Acids Protection Against Retinal and Choroidal Neovascularization Arterioscler Thromb Vasc Biol 2016.
Molecular Mechanisms and New Treatment Paradigm for Atrial Fibrillation Circ Arrhythm Electrophysiol 2016.
Novel Omega-3 Fatty Acid Epoxygenase Metabolite Reduces Kidney Fibrosis Int J Mol Sci 2016.
Pro-atherogenic role of smooth muscle Nox4-based NADPH oxidase J Mol Cell Cardiol 2016.
Soluble Epoxide Hydrolase Inhibition and Epoxyeicosatrienoic Acid Treatment Improve Vascularization of Engineered Skin Substitutes Plast Reconstr Surg Glob Open 2016
Soluble epoxide hydrolase inhibitor 1-trifluoromethoxyphenyl-3- (1-propionylpiperidin-4-yl) urea attenuates bleomycin-induced pulmonary fibrosis in mice Cell Tissue Res 2016.
Ingestion of the epoxide hydrolase inhibitor AUDA modulates immune responses of the mosquito, Culex quinquefasciatus during blood feeding. Insect Biochem Mol Biol. 2016 Sep;76:62-69. doi: 10.1016/j.ibmb.2016.06.011. Epub 2016 Jun 28.
"Turn-on" protein fluorescence: in situ formation of cyanine dyes J Am Chem Soc 2015
Endoplasmic reticulum stress in the peripheral nervous system is a significant driver of neuropathic pain Proc Natl Acad Sci U S A 2015.
Identification of potent inhibitors of the chicken soluble epoxide hydrolase Bioorg Med Chem Lett 2015.
Method for Sorting and Pairwise Selection of Nanobodies for the Development of Highly Sensitive Sandwich Immunoassays Anal Chem 2015.
PPARdelta signaling mediates the cytotoxicity of DHA in H9c2 cells Toxicol Lett 2015.
An omega-3 epoxide of docosahexaenoic acid lowers blood pressure in angiotensin-II-dependent hypertension J Cardiovasc Pharmacol 2014.
Effect of soluble epoxide hydrolase polymorphism on substrate and inhibitor selectivity and dimer formation J Lipid Res 2014.
Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy J Med Chem 2014.
Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors Bioorg Med Chem Lett 2014.
Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis Proc Natl Acad Sci U S A 2013.
Forster resonance energy transfer competitive displacement assay for human soluble epoxide hydrolase Anal Biochem 2013.
Rational design of a colorimetric pH sensor from a soluble retinoic acid chaperone J Am Chem Soc 2013.
Unique mechanistic insights into the beneficial effects of soluble epoxide hydrolase inhibitors in the prevention of cardiac fibrosis Proc Natl Acad Sci USA 2013.
Probing Wavelength Regulation with an Engineered Rhodopsin Mimic and a C15-Retinal Analogue Chempluschem 2012.
Tuning the electronic absorption of protein-embedded all-trans-retinal Science 2012.
Elucidating the exact role of engineered CRABPII residues for the formation of a retinal protonated Schiff base Proteins 2009.
Remarkable axial ligand effect on regioselectivity towards terminal alkenes in epoxidation of dienes by a robust manganese porphyrin Chemical Communications 2003-02-20.