Synthesis of Cyclooxygenase Metabolites of 8,9-epoxyeicosatrienoic Acid (EET): 11- and 15-hydroxy 8,9-EETs

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2017 May 5

PMID 28470279

Citations 3

Authors

Bogdan Barnych

Amy A Rand

Tomas cajka

Kin Sing Stephen Lee

Bruce D Hammock

Affiliations

Soon will be listed here.

Abstract

COX metabolites of 8,9-EET, previously observed as potent mitogenic lipid mediators, were synthesized for the first time by using two synthetic approaches. These synthetic materials allow for structural confirmation of COX metabolites of 8,9-EET and further study of their biological roles.

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References

Teder T, Boeglin W, Brash A . Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction. J Lipid Res. 2014; 55(12):2587-96. PMC: 4242451. DOI: 10.1194/jlr.M054072. View

Medhora M, Daniels J, Mundey K, Fisslthaler B, Busse R, Jacobs E . Epoxygenase-driven angiogenesis in human lung microvascular endothelial cells. Am J Physiol Heart Circ Physiol. 2002; 284(1):H215-24. DOI: 10.1152/ajpheart.01118.2001. View

Le Quere V, Plee-Gautier E, Potin P, Madec S, Salaun J . Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides. J Lipid Res. 2004; 45(8):1446-58. DOI: 10.1194/jlr.M300463-JLR200. View

Zhang J, Prakash C, Yamashita K, Blair I . Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem Biophys Res Commun. 1992; 183(1):138-43. DOI: 10.1016/0006-291x(92)91619-2. View

Zhang G, Panigrahy D, Hwang S, Yang J, Mahakian L, Wettersten H . Dual inhibition of cyclooxygenase-2 and soluble epoxide hydrolase synergistically suppresses primary tumor growth and metastasis. Proc Natl Acad Sci U S A. 2014; 111(30):11127-32. PMC: 4121808. DOI: 10.1073/pnas.1410432111. View

Rand A, Barnych B, Morisseau C, cajka T, Lee K, Panigrahy D . Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc Natl Acad Sci U S A. 2017; 114(17):4370-4375. PMC: 5410821. DOI: 10.1073/pnas.1616893114. View

Yin H, Xu L, Porter N . Free radical lipid peroxidation: mechanisms and analysis. Chem Rev. 2011; 111(10):5944-72. DOI: 10.1021/cr200084z. View

Falck J, Reddy L, Byun K, Campbell W, Yi X . Epoxygenase eicosanoids: synthesis of tetrahydrofuran-diol metabolites and their vasoactivity. Bioorg Med Chem Lett. 2007; 17(9):2634-8. PMC: 1950572. DOI: 10.1016/j.bmcl.2007.01.096. View

Panigrahy D, Greene E, Pozzi A, Wang D, Zeldin D . EET signaling in cancer. Cancer Metastasis Rev. 2011; 30(3-4):525-40. PMC: 3804913. DOI: 10.1007/s10555-011-9315-y. View

10.

Zeldin D . Epoxygenase pathways of arachidonic acid metabolism. J Biol Chem. 2001; 276(39):36059-62. DOI: 10.1074/jbc.R100030200. View

11.

Punta C, Rector C, Porter N . Peroxidation of polyunsaturated fatty acid methyl esters catalyzed by N-methyl benzohydroxamic acid: a new and convenient method for selective synthesis of hydroperoxides and alcohols. Chem Res Toxicol. 2005; 18(2):349-56. DOI: 10.1021/tx049685x. View

12.

Halarnkar P, Nourooz-Zadeh J, Kuwano E, Jones A, Hammock B . Formation of cyclic products from the diepoxide of long-chain fatty esters by cytosolic epoxide hydrolase. Arch Biochem Biophys. 1992; 294(2):586-93. DOI: 10.1016/0003-9861(92)90729-g. View

13.

Fleming I . Epoxyeicosatrienoic acids, cell signaling and angiogenesis. Prostaglandins Other Lipid Mediat. 2006; 82(1-4):60-7. DOI: 10.1016/j.prostaglandins.2006.05.003. View

14.

Pratt D, Tallman K, Porter N . Free radical oxidation of polyunsaturated lipids: New mechanistic insights and the development of peroxyl radical clocks. Acc Chem Res. 2011; 44(6):458-67. PMC: 3124811. DOI: 10.1021/ar200024c. View

15.

Darwish A, Lang A, Kim T, Chong J . The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes: synthesis of (E)-1-tributylstannyl-1-alkenes. Org Lett. 2008; 10(5):861-4. DOI: 10.1021/ol702982x. View

16.

Moreland K, Procknow J, Sprague R, Iverson J, Lonigro A, Stephenson A . Cyclooxygenase (COX)-1 and COX-2 participate in 5,6-epoxyeicosatrienoic acid-induced contraction of rabbit intralobar pulmonary arteries. J Pharmacol Exp Ther. 2007; 321(2):446-54. DOI: 10.1124/jpet.106.107904. View

17.

Pozzi A, Macias-Perez I, Abair T, Wei S, Su Y, Zent R . Characterization of 5,6- and 8,9-epoxyeicosatrienoic acids (5,6- and 8,9-EET) as potent in vivo angiogenic lipids. J Biol Chem. 2005; 280(29):27138-46. DOI: 10.1074/jbc.M501730200. View

18.

Homma T, Zhang J, Shimizu T, Prakash C, Blair I, Harris R . Cyclooxygenase-derived metabolites of 8,9-epoxyeicosatrienoic acid are potent mitogens for cultured rat glomerular mesangial cells. Biochem Biophys Res Commun. 1993; 191(1):282-8. DOI: 10.1006/bbrc.1993.1214. View

19.

Gallagher W, Terstiege I, Maleczka Jr R . Stille couplings catalytic in tin: the "Sn-O" approach. J Am Chem Soc. 2001; 123(14):3194-204. DOI: 10.1021/ja0035295. View

20.

Newman J, Morisseau C, Hammock B . Epoxide hydrolases: their roles and interactions with lipid metabolism. Prog Lipid Res. 2005; 44(1):1-51. DOI: 10.1016/j.plipres.2004.10.001. View