Nonenzymatic free radical-catalyzed generation of 15-deoxy-Δ 12,14- Prostaglandin J 2-like compounds (deoxy-J 2-isoprostanes) in vivo 1

Journal of Lipid Research

Volumn 52, Issue 1, 2011, Pages 113-124

  Hardy, Klarissa D ^a,b   Cox, Brian E ^a   Milne, Ginger L ^a   Yin, Huiyong ^a   Roberts II, L Jackson ^a,b  

^a Division of Clinical Pharmacology   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

15 d PGJ 2; Cyclopentenone eicosanoid; Isoprostane; Lipid peroxidation; Oxidant stress

Indexed keywords

15 DEOXY DELTA12,14 PROSTAGLANDIN J2 DERIVATIVE; ARACHIDONIC ACID; CARBON TETRACHLORIDE; DEOXY J2 ISOPROSTATE DERIVATIVE; FREE RADICAL; PROSTAGLANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; IN VIVO STUDY; LIPID PEROXIDATION; LIQUID CHROMATOGRAPHY; LIVER PARENCHYMA; MALE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; RAT; SIGNAL TRANSDUCTION; TANDEM MASS SPECTROMETRY;

ANIMALS; ARACHIDONIC ACID; CATALYSIS; FREE RADICALS; GLUTATHIONE; HUMANS; ISOPROSTANES; KINETICS; LIGANDS; LIVER; MALE; OXIDATIVE STRESS; PROSTAGLANDIN D2; RATS; RATS, SPRAGUE-DAWLEY;

EID: 78650919059     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M010264     Document Type: Article

References (58)

1. Hardman , J. G. , and L. E. Limbird , editors. 2001 . Goodman and Gilman's The Pharmacological Basis of Therapeutics . 10th edition . McGraw-Hill Book Co , NY . 669-679.
2. Marnett , L. J. 2000 . Cyclooxygenase mechanisms. Curr. Opin. Chem. Biol. 4 : 545-552.
3. Marnett , L. J. , S. W. Rowlinson , D. C. Goodwin , A. S. Kalgutkar , and C. A. Lanzo . 1999 . Arachidonic acid oxygenation by COX-1 and COX-2. Mechanisms of catalysis and inhibition. J. Biol. Chem. 274 : 22903-22906.
4. Hamberg , M. , and B. Samuelsson . 1966 . Prostaglandins in human seminal plasma. Prostaglandins and related factors 46. J. Biol. Chem. 241 : 257-263.
5. Fitzpatrick , F. A. , and M. A. Wynalda . 1983 . Albumin-catalyzed metabolism of prostaglandin D2. Identification of products formed in vitro. J. Biol. Chem. 258 : 11713-11718.
6. Straus , D. S. , and C. K. Glass . 2001 . Cyclopentenone prostaglandins: new Insights on biological activities and cellular targets. Med. Res. Rev. 21 : 185-210.
7. 2 as a potential endogenous regulator of redox-sentitive transcriptor factors. Biochem. Pharmacol. 72 : 1516-1528.
8. 2 : an electrophilic trigger of cellular responses. Chem. Res. Toxicol. 21 : 138-144.
9. Forman , B. M. , P. Tontonoz , C. Jasmine , R. P. Brun , B. M. Spiegelman , and R. M. Evans . 1995 . 15-deoxy- δ12,14 -prostaglandin J 2 is a ligand for the adipocyte determination factor PPAR γ . Cell . 83 : 803-812.
10. Halliwell , B. , and J. M. Gutteridge . 1990 . Role of free radicals and catalytic metal ions in human disease: an overview. Methods Enzymol. 186 : 1-85.
11. Southorn , P. A. , and G. Powis . 1988 . Free radicals in medicine. II. Involvement in human disease. Mayo Clin. Proc. 63 : 390-408.
12. Ames , B. N. 1983 . Dietary carcinogens and anticarcinogens. Oxygen radicals and degenerative diseases. Science . 221 : 1256-1264 . 13.
13. Harman , D. 1981 . The aging process. Proc. Natl. Acad. Sci. U S A . 78 : 7124-7128.
14. 2 -like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc. Natl. Acad. Sci. U S A . 87 : 9383-9387.
15. 2-isoprostanes from esterified phospholipids is catalyzed by intracellular and plasma plateletactivating factor acetylhydrolases. J. Biol. Chem. 281 : 4616-4623.
16. 2 -isoprostanes) are formed in situ on phospholipids. Proc. Natl. Acad. Sci. USA . 89 : 10721-10725.
17. Prtyor , W. A. , J. P. Stanley , and E. Blair . 1976 . Autoxidation of polyunsaturated fatty acids: II. A suggested mechanism for the formation of TBA-reactive materials from prostaglandin-like endoperoxides. Lipids . 11 : 370-379.
18. Morrow , J. D. , T. M. Harris , and L. J. Roberts II . 1990 . Noncyclooxygenase oxidative formation of a series of novel prostaglandins: analytical ramifi cations for measurement of eicosanoids. Anal. Biochem. 184 : 1-10.
19. Morrow , J. D. , T. A. Minton , C. R. Mukundan , M. D. Campbell , W. E. Zachert , V. C. Daniel , K. F. Badr , I. K. Blair , and L. J. Roberts II . 1994 . Free radical-induced generation of isoprostanes in vivo: evidence for the formation of D-ring and E-ring isoprostanes. J. Biol. Chem. 269 : 4317-4326.
20. Taber , D. F. , J. D. Morrow , and L. J. Roberts II . 1997 . A nomenclature system for the isoprostanes. Prostaglandins . 53 : 63-67.
21. 12 -13,14- dihydroprostaglandin D2in human urine. J. Biol. Chem. 263 : 16619-16625.
22. 12,14 -PGJ 2 and the ligation of PPAR γ . J. Clin. Invest. 112 : 945-955.
23. Attallah , A. , W. Payakkapan , J. Lee , A. Carr , and E. Brazelton . 1974 . PGA: fact, not artifact. Prostaglandins . 5 : 69-71.
24. Jonsson , H. T. , B. S. Middledtich , M. A. Schexnayder , and D. M. Desiderio . 1976 . 11,15,19-trihydroxy-9-ketoprost-13-enoic acid and 11,15,19-trihydroxy-9-ketoprosta-5, 13-dienoic acid in human seminal fl uid. J. Lipid Res. 17 : 1-6.
25. Chen , Y. , J. D. Morrow , and L. J. Roberts II . 1999 . Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway. J. Biol. Chem. 274 : 10863-10868.
26. 2is metabolized by Hep G2 cells via conjugation with glutathione. Chem. Res. Toxicol. 20 : 1528-1535.
27. 2), is effi ciently conjugated with glutathione by human and rat glutathione transferase A4-4. Chem. Res. Toxicol. 15 : 1113-1118.
28. 2t -isoprostane, is efficiently metabolized by HepG2 cells via conjugation with glutathione. Chem. Res. Toxicol. 17 : 17-25.
29. 2 , to glutathione. Biochim. Biophys. Acta . 1584 : 37-45.
30. 12 (E)-prostaglandin D2. Biochemistry . 29 : 3760-3765.
31. 2via the isoprostane pathway: a mechanism for the generation of bioactive prostaglandins independent of cyclooxygenase. J. Biol. Chem. 278 : 28479-28489.
32. 2α is generated from the isoprostane pathway and not the cyclooxygenase in humans. J. Biol. Chem. 282 : 329-336.
33. 2) isoprostanes-unique, highly reactive products of arachidonic acid peroxidation. Antioxid. Redox Signal. 7 : 210-220.
34. Brechbuhl , H. M. , E. Min , C. Kariya , B. Frederick , D. Raben , and B. J. Day . 2009 . Selective cyclopentenone prostaglandins trigger glutathione efflux and the role of ABCG2 transport. Free Radic. Biol. Med. 47 : 722-730.
35. 2 . J. Biol. Chem. 274 : 17042-17048.
36. 2 on glutathione induction and apoptosis in human endothelial cells. Arterioscler. Thromb. Vasc. Biol. 21 : 1846-1851.
37. 12,14-prostaglandin J2-induced apoptosis does not require PPARgamma in breast cancer cells. J. Lipid Res. 43 : 1818-1828.
38. Hortelano , S. , A. Castillo , A. M. Alvarez , and L. Bosca . 2000 . Contribution of cyclopentenone prostaglandins to the resolution of inflammation through potentiation of apoptosis in activated macrophages. J. Immunol. 165 : 6525-6531.
39. Rossi , A. , P. Kapahi , G. Natoli , T. Takahashi , Y. Chen , M. Karin , and M. G. Santoro . 2000 . Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IkappaB kinase. Nature . 403 : 103-108.
40. 2 inhibits multiple steps in the NF- κ B signaling pathway. Proc. Natl. Acad. Sci. U S A . 97 : 4844-4849.
41. Perez-Sala , D. , E. Cernuda-Morollon , E. Pineda-Molina , and F. J. Canada . 2002 . Contribution of covalent protein Modification to the anti-inflammatory effects of cyclopentenone prostaglandins. Ann. N. Y. Acad. Sci. 973 : 533-536.
42. Shiraki , T. , N. Kamiya , S. Shiki , T. S. Kodama , A. Kakizuka , and H. Jingami . 2005 . α , β -Unsaturated ketone is a core moiety of natural ligands for covalent binding to peroxisome proliferator-activated receptor γ . J. Biol. Chem. 280 : 14145-14153.
43. Dinkova-Kostova , A. T. , W. D. Holtzclaw , R. N. Cole , K. Itoh , N. Wakabayashi , Y. Katoh , M. Yamamoto , and P. Talalay . 2002 . Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc. Natl. Acad. Sci. U S A . 99 : 11908-11913.
44. 2 . Mol. Cell. Biol. 24 : 36-45.
45. kim , E. H. , D. H. Kim , H. K. Na , and Y. J. Surh . 2004 . Effects of cyclopentenone prostaglandins on the expression of heme oxygenase- 1 in MCF-7 cells. Ann. N. Y. Acad. Sci. 1030 : 493-500.
46. 2 through up-regulation of cellular glutathione via different mechanisms. J. Biol. Chem. 281 : 14440-14445 . 47.
47. 2 in human mesangial cells. Kidney Int. 65 : 798-810.
48. 12,14)-prostaglandin J(2) induces G(1) arrest and differentiation marker expression in vascular smooth muscle cells. Mol. Pharmacol. 58: 837-844.
49. Wakino , S. , U. Kintscher , S. Kim , F. Yin , W. A. Hsueh , and R. E. Law . 2000 . Peroxisome proliferator-activated receptor gamma ligands inhibit retinoblastoma phosphorylation and G1→S transition in vascular smooth muscle cells. J. Biol. Chem. 275 : 22435-22441.
50. 2. A prostaglandin D2metabolite generated during inflammatory processes. J. Biol. Chem. 277 : 10459-10466.
51. Gilroy , D. W. , P. R. Colville-Nash , D. Willis , J. Chivers , M. J. Paul- Clark , and D. A. Willoughby . 1999 . Inducible cyclooxygenase may have anti-inflammatory properties. Nat. Med. 5 : 698-701.
52. 2 . Proc. Natl. Acad. Sci. USA . 104 : 20979-20984.
53. Berliner , J. A. , M. Navab , A. M. Fogelman , J. S. Frank , L. L. Demer , P. A. Edwards , A. D. Watson , and A. J. Luis . 1995 . Atherosclerosis: basic mechanisms-oxidation, inflammation, and genetics. Circulation . 91 : 2488-2496.
54. Berliner , J. , N. Leitinger , A. Watson , J. Huber , A. Fogelman , and M. Navab . 1997 . Oxidized lipids in atherogenesis: formation, destruction and action. Thromb. Haemost. 78 : 195-199.
55. Heinecke , J. W. 1998 . Oxidants and antioxidants in the pathogenesis of atherosclerosis: implications for the oxidized low density lipoprotein hypothesis. Atherosclerosis . 141 : 1-5.
56. Chisolm , G. M. , and D. Steinberg . 2000 . The oxidative Modification hypothesis of atherogenesis: an overview. Free Radic. Biol. Med. 18 : 1815-1826.
57. 2 in macrophages. J. Biol. Chem. 282 : 17964-17973.
58. 2t -Isoprostane in Vivo. J. Biol. Chem. 280 : 25178-25184.