Redox regulation of soluble epoxide hydrolase by 15-Deoxy-Δ- Prostaglandin J2 Controls coronary hypoxic vasodilation

Circulation Research

Volumn 108, Issue 3, 2011, Pages 324-334

  Charles, Rebecca L ^a   Burgoyne, Joseph R ^a   Mayr, Manuel ^b   Weldon, Steven M ^c   Hubner, Norbert ^d   Dong, Hua ^e   Morisseau, Christophe ^e   Hammock, Bruce D ^e   Landar, Aimee ^f   Eaton, Philip ^a  

^a ST THOMAS HOSPITAL   (United Kingdom)

^b KING'S COLLEGE LONDON   (United Kingdom)

^c BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^d MAX DELBRÜCK CENTER FOR MOLECULAR MEDICINE   (Germany)

^e UNIVERSITY OF CALIFORNIA   (United States)

^f University of Alabama at Birmingham   (United States)

Author keywords

15 deoxy prostaglandin J2 soluble epoxide hydrolase; hypoxia; redox signaling

Indexed keywords

14,15 EPOXYEICO 5 ENOIC ACID; 15 DEOXY DELTA PROSTAGLANDIN J2; EPOXIDE HYDROLASE; EPOXYICOSATRIENOIC ACID; HYDROLASE; PROSTAGLANDIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; CORONARY ARTERY DILATATION; CORONARY REPERFUSION; ENZYME INHIBITION; HYPOXIA; MOUSE; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEOMICS; RAT; SIGNAL TRANSDUCTION; VASCULARIZATION; WILD TYPE;

AMINO ACID SEQUENCE; ANIMALS; ANOXIA; EPOXIDE HYDROLASES; MICE; MICE, INBRED C57BL; MICE, KNOCKOUT; MODELS, ANIMAL; MOLECULAR SEQUENCE DATA; MYOCARDIUM; OXIDATION-REDUCTION; PROSTAGLANDIN D2; RATS; RATS, WISTAR; SIGNAL TRANSDUCTION; VASODILATION;

EID: 79751538990     PISSN: 00097330     EISSN: 15244571     Source Type: Journal    
DOI: 10.1161/CIRCRESAHA.110.235879     Document Type: Article

References (35)

1. Eaton P. Protein thiol oxidation in health and disease: techniques for measuring disulfides and related modifications in complex protein mixtures. Free Radic Biol Med. 2006;40:1889-1899. (Pubitemid 43744434)
2. Uchida K. Cellular response to bioactive lipid peroxidation products. Free Radic Res. 2000;33:731-737. (Pubitemid 32208481)
3. Waku T, Shiraki T, Oyama T, Morikawa K. Atomic structure of mutant PPARgamma LBD complexed with 15d-PGJ2: novel modulation mechanism of PPARgamma/RXRalpha function by covalently bound ligands. FEBS Lett. 2009;583:320-324.
4. Scher JU, Pillinger MH. 15d-PGJ2: the anti-inflammatory prostaglandin? Clin Immunol. 2005;114:100-109.
5. Shibata T, Yamada T, Ishii T, Kumazawa S, Nakamura H, Masutani H, Yodoi J, Uchida K. Thioredoxin as a molecular target of cyclopentenone prostaglandins. J Biol Chem. 2003;278:26046-26054. (Pubitemid 36835372)
6. Forman BM, Tontonoz P, Chen J, Brun RP, Spiegelman BM, Evans RM. 15-Deoxy-delta 12, 14-prostaglandin J2 is a ligand for the adipocyte determination factor PPAR gamma. Cell. 1995;83:803-812. (Pubitemid 3006324)
7. Zingarelli B, Hake PW, Mangeshkar P, O'Connor M, Burroughs TJ, Piraino G, Denenberg A, Wong HR. Diverse cardioprotective signaling mechanisms of peroxisome proliferator-activated receptor-gamma ligands, 15-deoxy-Delta12,14- prostaglandin J2 and ciglitazone, in reper-fusion injury: role of nuclear factor-kappaB, heat shock factor 1, and Akt. Shock. 2007;28:554-563. (Pubitemid 350287432)
8. Renedo M, Gayarre J, Garcia-Dominguez CA, Perez-Rodriguez A, Prieto A, Canada FJ, Rojas JM, Perez-Sala D. Modification and activation of Ras proteins by electrophilic prostanoids with different structure are site-selective. Biochemistry. 2007;46:6607-6616. (Pubitemid 46870126)
9. Mansure JJ, Nassim R, Kassouf W. Peroxisome proliferator-activated receptor gamma in bladder cancer: a promising therapeutic target. Cancer Biol Ther. 2009;8:6-15.
10. Koh SH, Jung B, Song CW, Kim Y, Kim YS, Kim SH. 15-Deoxy-delta12,14- prostaglandin J2, a neuroprotectant or a neurotoxicant? Toxicology. 2005;216:232-243. (Pubitemid 41712012)
11. Cuzzocrea S, Pisano B, Dugo L, Ianaro A, Patel NS, Di Paola R, Genovese T, Chatterjee PK, Di Rosa M, Caputi AP, Thiemermann C. Rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2, ligands of the peroxisome proliferator-activated receptor-gamma (PPAR-gamma), reduce ischaemia/reperfusion injury of the gut. Br J Pharmacol. 2003; 140:366-376. (Pubitemid 37249197)
12. Wayman NS, Hattori Y, McDonald MC, Mota-Filipe H, Cuzzocrea S, Pisano B, Chatterjee PK, Thiemermann C. Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. FASEB J. 2002;16:1027-1040. (Pubitemid 34753509)
13. Cuzzocrea S. Peroxisome proliferator-activated receptors and acute lung injury. Curr Opin Pharmacol. 2006;6:263-270.
14. Imig JD, Hammock BD. Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases. Nat Rev Drug Discov. 2009;8:794-805.
15. Hasegawa LS, Hammock BD. Spectrophotometric assay for mammalian cytosolic epoxide hydrolase using trans-stilbene oxide as the substrate. Biochem Pharmacol. 1982;31:1979-1984. (Pubitemid 12074411)
16. Chiamvimonvat N, Ho CM, Tsai HJ, Hammock BD. The soluble epoxide hydrolase as a pharmaceutical target for hypertension. J Cardiovasc Pharmacol. 2007;50:225-237. (Pubitemid 47428969)
17. Pinot F, Grant DF, Beetham JK, Parker AG, Borhan B, Landt S, Jones AD, Hammock BD. Molecular and biochemical evidence for the involvement of the Asp-333-His-523 pair in the catalytic mechanism of soluble epoxide hydrolase. J Biol Chem. 1995;270:7968-7974.
18. Ricote M, Li AC, Willson TM, Kelly CJ, Glass CK. The peroxisome proliferator-activated receptor-gamma is a negative regulator of macro-phage activation. Nature. 1998;391:79-82. (Pubitemid 28079218)
19. Burgoyne JR, Eaton P. Transnitrosylating nitric oxide species directly activate type I protein kinase A, providing a novel adenylate cyclase-independent cross-talk to beta-adrenergic-like signaling. J Biol Chem. 2009;284:29260-29268.
20. Luria A, Weldon SM, Kabcenell AK, Ingraham RH, Matera D, Jiang H, Gill R, Morisseau C, Newman JW, Hammock BD. Compensatory mechanism for homeostatic blood pressure regulation in Ephx2 gene-disrupted mice. J Biol Chem. 2007;282:2891-2898. (Pubitemid 47084334)
21. Wright DH, Nantel F, Metters KM, Ford-Hutchinson AW. A novel biological role for prostaglandin D-2 is suggested by distribution studies of the rat DP prostanoid receptor. Eur J Pharmacol. 1999;377:101-115. (Pubitemid 29322765)
22. Sinal CJ, Miyata M, Tohkin M, Nagata K, Bend JR, Gonzalez FJ. Targeted disruption of soluble epoxide hydrolase reveals a role in blood pressure regulation. J Biol Chem. 2000;275:40504-40510. (Pubitemid 32064687)
23. Keseru B, Barbosa-Sicard E, Schermuly RT, Tanaka H, Hammock BD, Weissmann N, Fisslthaler B, Fleming I. Hypoxia-induced pulmonary hypertension: comparison of soluble epoxide hydrolase deletion vs. inhibition. Cardiovasc Res. 2010;85:232-240.
24. Charles RL, Schroder E, May G, Free P, Gaffney PR, Wait R, Begum S, Heads RJ, Eaton P. Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue. Mol Cell Pro-teomics. 2007;6:1473-1484. (Pubitemid 47506161)
25. Ikeda U, Shimpo M, Murakami Y, Shimada K. Peroxisome proliferator- activated receptor-gamma ligands inhibit nitric oxide synthesis in vascular smooth muscle cells. Hypertension. 2000;35:1232-1236. (Pubitemid 30413656)
26. Shan ZZ, Masuko-Hongo K, Dai SM, Nakamura H, Kato T, Nishioka K. A potential role of 15-deoxy-Delta(12,14)-prostaglandin J2 for induction of human articular chondrocyte apoptosis in arthritis. J Biol Chem. 2004; 279:37939-37950. (Pubitemid 39195509)
27. Eaton P, Li JM, Hearse DJ, Shattock MJ. Formation of 4-hydroxy-2-nonenal- modified proteins in ischemic rat heart. Am J Physiol. 1999;45: H935-H943. (Pubitemid 29157466)
28. Rudolph V, Rudolph TK, Schopfer FJ, Bonacci G, Woodcock SR, Cole MP, Baker PRS, Ramani R, Freeman BA. Endogenous generation and protective effects of nitro-fatty acids in a murine model of focal cardiac ischaemia and reperfusion. Cardiovasc Res. 2010;85:155-166.
29. Seubert JM, Sinal CJ, Graves J, DeGraff LM, Bradbury JA, Lee CR, Goralski K, Carey MA, Luria A, Newman JW, Hammock BD, Falck JR, Roberts H, Rockman HA, Murphy E, Zeldin DC. Role of soluble epoxide hydrolase in postischemic recovery of heart contractile function. Circ Res. 2006;99:442-450. (Pubitemid 44253701)
30. Kelley EE, Khoo NKH, Hundley NJ, Malik UZ, Freeman BA, Tarpey MM. Hydrogen peroxide is the major oxidant product of xanthine oxidase. Free Radic Biol Med. 2010;48:493-498.
31. Kelley EE, Batthyany CI, Hundley NJ, Woodcock SR, Bonacci G, Del Rio JM, Schopfer FJ, Lancaster JR Jr, Freeman BA, Tarpey MM. Nitro-oleic acid, a novel and irreversible inhibitor of xanthine oxi-doreductase. J Biol Chem. 2008;283:36176-36184.
32. Kelley EE, Hock T, Khoo NKH, Richardson GR, Johnson KK, Powell PC, Giles GI, Agarwal A, Lancaster JR, Tarpey MM. Moderate hypoxia induces xanthine oxidoreductase activity in arterial endothelial cells. Free Radic Biol Med. 2006;40:952-959. (Pubitemid 43376004)
33. Barbosa-Sicard E, Fromel T, Keseru B, Brandes RP, Morisseau C, Hammock BD, Braun T, Kruger M, Fleming I. Inhibition of the soluble epoxide hydrolase by tyrosine nitration. J Biol Chem. 2009;284: 28156-28163.
34. Imig JD. Cardiovascular therapeutic aspects of soluble epoxide hydrolase inhibitors. Cardiovasc Drug Rev. 2006;24:169-188. (Pubitemid 46696923)
35. Monti J, Fischer J, Paskas S, Heinig M, Schulz H, Gosele C, Heuser A, Fischer R, Schmidt C, Schirdewan A, Gross V, Hummel O, Maatz H, Patone G, Saar K, Vingron M, Weldon SM, Lindpaintner K, Hammock BD, Rohde K, Dietz R, Cook SA, Schunck WH, Luft FC, Hubner N. Soluble epoxide hydrolase is a susceptibility factor for heart failure in a rat model of human disease. Nat Genet. 2008;40:529-537. (Pubitemid 351601216)