Cyclooxygenase reaction mechanism of PGHS - Evidence for a reversible transition between a pentadienyl radical and a new tyrosyl radical by nitric oxide trapping

Journal of Inorganic Biochemistry

Volumn 105, Issue 3, 2011, Pages 356-365

  Lü, Jian Ming ^a   Rogge, Corina E ^b   Wu, Gang ^a   Kulmacz, Richard J ^a   Van Der Donk, Wilfred A ^c   Tsai, Ah Lim ^a  

^a UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

^b BUFFALO STATE COLLEGE   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

AA induced radical; HPLC MS analysis; NO trapping

Indexed keywords

3 NITROTYROSINE; ARACHIDIC ACID; CARBON 14; HEME; HYDROPEROXIDE DERIVATIVE; NITRIC OXIDE; OXIME; PROSTAGLANDIN H1 SYNTHASE; PROSTAGLANDIN SYNTHASE; RADICAL; TYROSINE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL BOND; CONCENTRATION (PARAMETERS); CONJUGATION; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; ENZYME INACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOBLOTTING; ISOTOPE LABELING; MASS SPECTROMETRY; METABOLITE;

ALKADIENES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HUMANS; MASS SPECTROMETRY; NITRIC OXIDE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; TEMPERATURE; TYROSINE;

EID: 79952988114     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2010.11.013     Document Type: Article

References (45)

1. C.A. Rouzer, and L.J. Marnett Chem. Rev. 103 2003 2239 2304
2. W.L. Smith, and D.L. Dewitt Adv. Immunol. 62 1996 167 215
3. A.M. Lambeir, C.M. Markey, H.B. Dunford, and L.J. Marnett J. Biol. Chem. 260 1985 14894 14896
4. R. Dietz, W. Nastainczyk, and H.H. Ruf Eur. J. Biochem. 171 1988 321 328
5. R. Karthein, R. Dietz, W. Nastainczyk, and H.H. Ruf Eur. J. Biochem. 171 1988 313 320
6. R.J. Kulmacz, Y. Ren, A.-L. Tsai, and G. Palmer Biochemistry 29 1990 8760 8771
7. A.-L. Tsai, R.J. Kulmacz, and G. Palmer J. Biol. Chem. 270 1995 10503 10508
8. A.-L. Tsai, G. Palmer, G. Xiao, D.C. Swinney, and R.J. Kulmacz J. Biol. Chem. 273 1998 3888 3894
9. R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, R.A. Stegeman, J.Y. Pak, D. Gildehaus, J.M. Miyashiro, T.D. Penning, K. Seibert, P.C. Isakson, and W.C. Stallings Nature 384 1996 644 648
10. M.G. Malkowski, S.L. Ginell, W.L. Smith, and R.M. Garavito Science 289 2000 1933 1937
11. D. Picot, P.J. Loll, and R.M. Garavito Nature 367 1994 243 249
12. S. Peng, N.M. Okeley, A.-L. Tsai, G. Wu, R.J. Kulmacz, and W.A. van der Donk J. Am. Chem. Soc. 123 2001 3609 3610
13. S. Peng, N.M. Okeley, A.-L. Tsai, G. Wu, R.J. Kulmacz, and W.A. van der Donk J. Am. Chem. Soc. 124 2002 10785 10796
14. A.-L. Tsai, G. Palmer, G. Wu, S. Peng, N.M. Okeley, W.A. van der Donk, and R.J. Kulmacz J. Biol. Chem. 277 2002 38311 38321
15. E.G. Bascetta, D. Frank, C.M. Scrimgeour, and J.C. Walton J. Chem. Soc. Chem. Commun. 1982 110 112
16. C.E. Rogge, W. Liu, G. Wu, L.H. Wang, R.J. Kulmacz, and A.-L. Tsai Biochemistry 43 2004 1560 1568
17. C.E. Rogge, W. Liu, R.J. Kulmacz, and A.-L. Tsai J. Inorg. Biochem. 103 2009 912 922
18. P. Dorlet, S.A. Seibold, G.T. Babcock, G.J. Gerfen, W.L. Smith, A.-L. Tsai, and S. Un Biochemistry 41 2002 6107 6114
19. W. Shi, C.W. Hoganson, M. Espe, C.J. Bender, G.T. Babcock, G. Palmer, R.J. Kulmacz, and A.-L. Tsai Biochemistry 39 2000 4112 4121
20. D.C. Goodwin, M.R. Gunther, L.C. Hsi, B.C. Crews, T.E. Eling, R.P. Mason, and L.J. Marnett J. Biol. Chem. 273 1998 8903 8909
21. D.C. Goodwin, L.M. Landino, and L.J. Marnett FASEB J. 13 1999 1121 1136
22. M.R. Gunther, L.C. Hsi, J.F. Curtis, J.K. Gierse, L.J. Marnett, T.E. Eling, and R.P. Mason J. Biol. Chem. 272 1997 17086 17090
23. M.R. Gunther, B.E. Sturgeon, and R.P. Mason Toxicology 177 2002 1 9
24. J. Schreiber, T.E. Eling, and R.P. Mason Arch. Biochem. Biophys. 249 1986 126 136
25. R.J. Kulmacz, and L.H. Wang J. Biol. Chem. 270 1995 24019 24023
26. R.J. Kulmacz, and W.E.M. Lands C. Benedetto, R.G. McDonald-Gibson, S. Nigam, T.F. Slater, Prostaglandins and Related Substances: A Practical Approach 1987 IRL Press Washington, DC 209 227
27. G. Xiao, A.-L. Tsai, G. Palmer, W.C. Boyar, P.J. Marshall, and R.J. Kulmacz Biochemistry 36 1997 1836 1845
28. G. Wu, A.-L. Tsai, and R.J. Kulmacz Biochemistry 48 2009 11902 11911
29. J. March Advanced Organic Chemistry, Reactions, Mechanisms, and Structure 4th ed 1992 John Wiley & Sons 593
30. M. Hamberg, and B. Samuelsson J. Biol. Chem. 242 1967 5336 5343
31. J.P. Eiserich, J. Butler, A. van der Vliet, C.E. Cross, and B. Halliwell Biochem. J. 310 Pt 3 1995 745 749
32. Y. Sanakis, C. Goussias, R.P. Mason, and V. Petrouleas Biochemistry 36 1997 1411 1417
33. T. Shimokawa, R.J. Kulmacz, D.L. DeWitt, and W.L. Smith J. Biol. Chem. 265 1990 20073 20076
34. B.A. Barry, M.K. El-Deeb, P.O. Sandusky, and G.T. Babcock J. Biol. Chem. 265 1990 20139 20143
35. A.-L. Tsai, L.C. Hsi, R.J. Kulmacz, G. Palmer, and W.L. Smith J. Biol. Chem. 269 1994 5085 5091
36. A.-L. Tsai, and R.J. Kulmacz Prostaglandins Other Lipid Mediat. 62 2000 231 254
37. A.-L. Tsai, G. Wu, G. Palmer, B. Bambai, J.A. Koehn, P.J. Marshall, and R.J. Kulmacz J. Biol. Chem. 274 1999 21695 21700
38. A. Mukherjee, D.W. Brinkley, K.M. Chang, and J.P. Roth Biochemistry 46 2007 3975 3989
39. K. Gupta, B.S. Selinsky, and P.J. Loll Acta Crystallogr. D Biol. Crystallogr. 62 2006 151 156
40. B.S. Selinsky, K. Gupta, C.T. Sharkey, and P.J. Loll Biochemistry 40 2001 5172 5180
41. Y.N. Chen, M.J. Bienkowski, and L.J. Marnett J. Biol. Chem. 262 1987 16892 16899
42. R.J. Kulmacz J. Biol. Chem. 264 1989 14136 14144
43. J.J. Prusakiewicz, K.C. Duggan, C.A. Rouzer, and L.J. Marnett Biochemistry 48 2009 7353 7355
44. C. Yuan, C.J. Rieke, G. Rimon, B.A. Wingerd, and W.L. Smith Proc. Natl Acad. Sci. USA 103 2006 6142 6147
45. C. Yuan, R.S. Sidhu, D.V. Kuklev, Y. Kado, M. Wada, I. Song, and W.L. Smith J. Biol. Chem. 284 2009 10046 10055