Prostaglandin endoperoxide H synthases: Peroxidase hydroperoxide specificity and cyclooxygenase activation

Journal of Biological Chemistry

Volumn 282, Issue 25, 2007, Pages 18233-18244

  Liu, Jiayan ^a   Seibold, Steve A ^b   Rieke, Caroline J ^c   Song, Inseok ^c   Cukier, Robert I ^b   Smith, William L ^a,c  

^a Michigan State University   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DISSOCIATION; ELECTRON TRANSPORT PROPERTIES; ENZYME KINETICS; HYDROPHOBICITY; POSITIVE IONS;

ARACHIDONIC ACID; HYDROPEROXIDE; PROSTAGLANDIN ENDOPEROXIDE H SYNTHASES (PGHS);

FATTY ACIDS;

15 HYDROPEROXYARACHIDONIC ACID; ALANINE DERIVATIVE; ARACHIDONIC ACID; CARBENE; HEME; HETERODIMER; HISTIDINE DERIVATIVE; HYDROGEN PEROXIDE; HYDROPEROXIDE; MONOMER; OXYGEN; PEROXIDASE; PROSTAGLANDIN G2; PROSTAGLANDIN SYNTHASE; PROTOPORPHYRIN; TYROSINE DERIVATIVE;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME BINDING; ENZYME SPECIFICITY; ENZYME STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DYNAMICS; MUTATION; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN INTERACTION; SIMULATION;

AMINO ACID SEQUENCE; ANIMALS; CYCLOOXYGENASE 1; DIMERIZATION; ENZYME ACTIVATION; HUMANS; HYDROGEN PEROXIDE; MICE; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; OXYGEN CONSUMPTION; PEROXIDASES; SEQUENCE HOMOLOGY, AMINO ACID; SHEEP; SUBSTRATE SPECIFICITY;

EID: 34547137409     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M701235200     Document Type: Article

References (81)

1. Smith, W. L., DeWitt, D. L., and Garavito, R. M. (2000) Annu. Rev. Biochem. 69, 145-182
2. Kulmacz, R. J., van der Donk, W. A., and Tsai, A. L. (2003) Prog. Lipid Res. 42, 377-404
3. Rouzer, C., and Marnett, L. (2003) Chem. Rev. 103, 2239-2304
4. Rollins, T. E., and Smith, W. L. (1980) J. Biol. Chem. 255, 4872-4875
5. Smith, W. L., Rollins, T. E., and DeWitt, D. L. (1981) Prog. Lipid Res. 20, 103-110
6. Spencer, A. G., Woods, J. W., Arakawa, T., Singer, I. I., and Smith, W. L. (1998) J. Biol. Chem. 273, 9886-9893
7. Otto, J. C., and Smith, W. L. (1995) Adv. Prostaglandin Thromboxane Leukotriene Res. 23, 29-34
8. Tanabe, T., and Tohnai, N. (2002) Prostaglandins Other Lipid Mediat. 68-69, 95-114
9. Kang, Y.-J., Mbonye, U. R., DeLong, C. J., Wada, M., and Smith, W. L. (2007) Prog. Lipid Res. 46, 108-125
10. Schulz, C. E., Rutter, R., Sage, J. T., Debrunner, P. G., and Hager, L. P. (1984) Biochemistry 23, 4743-4754
11. Ortiz de Montellano, P. (1995) Cytochrome P450: Structure, Mechanism and Biochemistry, pp. 49-80, Plenum Press, New York
12. Patterson, W. R., Poulos, T. L., and Goodin, D. B. (1995) Biochemistry 34, 4342-4345
13. Benecky, M. J., Frew, J. E., Scowen, N., Jones, P., and Hoffman, B. M. (1993) Biochemistry 32, 11929-11933
14. Karthein, R., Dietz, R., Nastainczyk, W., and Ruf, H. H. (1988) Eur. J. Biochem. 171, 313-320
15. Dietz, R., Nastainczyk, W., and Ruf, H. H. (1988) Eur. J. Biochem. 171, 321-328
16. Erman, J. E., Vitello, L. B., Mauro, J. M., and Kraut, J. (1989) Biochemistry 28, 7992-7995
17. Houseman, A. L., Doan, P. E., Goodin, D. B., and Hoffman, B. M. (1993) Biochemistry 32, 4430-4443
18. Huyett, J. E., Choudhury, S. B., Eichhorn, D. M., Bryngelson, P. A., Maroney, M. J., and Hoffman, B. M. (1998) Inorg. Chem. 37, 1361-1367
19. Sivaraja, M., Goodin, D. B., Smith, M., and Hoffman, B. M. (1989) Science 245, 738-740
20. Hamberg, M., and Samuelsson, B. (1967) J. Biol. Chem. 242, 5336-5343
21. Tsai, A., Wei, C., Baek, H. K., Kulmacz, R. J., and Van Wart, H. E. (1997) J. Biol. Chem. 272, 8885-8894
22. Landino, L. M., and Marnett, L. J. (1996) Biochemistry 35, 2637-2643
23. Strieder, S., Schaible, K., Scherer, H. J., Dietz, R., and Ruf, H. H. (1992) J. Biol. Chem. 267, 13870-13878
24. Lu, G., Tsai, A. L., Van Wart, H. E., and Kulmacz, R. J. (1999) J. Biol. Chem. 274, 16162-16167
25. Reddy, S. T., and Herschman, H. R. (1994) J. Biol. Chem. 269, 15473-15480
26. Shitashige, M., Morita, I., and Murota, S. (1998) Biochim. Biophys. Acta 1389, 57-66
27. Malkowski, M. G., Ginell, S. L., Smith, W. L., and Garavito, R. M. (2000) Science 289, 1933-1937
28. Picot, D., Loll, P. J., and Garavito, R. M. (1994) Nature 367, 243-249
29. Seibold, S. A., Smith, W. L., and Cukier, R. I. (2004) J. Phys. Chem. B 108, 9297-9305
30. Chubb, A. J., Fitzgerald, D. J., Nolan, K. B., and Moman, E. (2006) Biochemistry 45, 811-820
31. Seibold, S. A., Cerda, J. F., Mulichak, A. M., Song, I., Garavito, R. M., Arakawa, T., Smith, W. L., and Babcock, G. T. (2000) Biochemistry 39, 6616-6624
32. Yuan, C., Rieke, C. J., Rimon, G., Wingerd, B. A., and Smith, W. L. (2006) Proc. Natl. Acad. Sci. U. S. A. 103, 6142-6147
33. Graff, G. (1982) Methods Enzymol. 86, 386-392
34. Smith, T., Leipprandt, J., and DeWitt, D. (2000) Arch. Biochem. Biophys. 375, 195-200
35. Song, I., Ball, T. M., and Smith, W. L. (2001) Biochem. Biophys. Res. Commun. 289, 869-875
36. Putter, J. (1975) Methods of Enzymatic Analysis, pp. 685-690, Verlag Chemie, Weinheim, Germany
37. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, J. A., Jr., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Salvador, P., Dannenberg, J. J., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Baboul, A. G., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Andres, J. L., Gonzalez, C., Head-Gordon, M., Replogle, E. S., and Pople, J. A. (2001) Gaussian 98, Revision A.11.1 Ed., Gaussian, Inc., Pittsburg, PA
38. MOE (2003) Molecular Operating Environment, Chemical Computing Co., Montreal, Quebec H3B 3X3, Canada
39. Case, D. A., Pearlman, D. A., Caldwell, J. W., Wang, J., Ross, W. S., Simmerling, C. L., Darden, T. A., Mertz, K. M., Stanton, R. V., Cheng, A. L., Vincent, J. J., Crowley, M., Tsue, V., Gohlke, H., Radmer, R., Duan, Y., Pitera, J., Massova, I., Seibel, G. L., Singh, C., Weiner, P., and Kollman, P. A. (2002) AMBER Simulation Software Package, Version 7, Unversity of California, San Francisco, CA
40. DeGray, J. A., Lassmann, G., Curtis, J. F., Kennedy, T. A., Marnett, L. J., Eling, T. E., and Mason, R. P. (1992) J. Biol. Chem. 267, 23583-23588
41. Wu, G., Vuletich, J. L., Kulmacz, R. J., Osawa, Y., and Tsai, A. L. (2001) J. Biol. Chem. 276, 19879-19888
42. Wu, G., Kulmacz, R. J., and Tsai, A. L. (2003) Biochemistry 42, 13772-13777
43. Ohki, S., Ogino, N., Yamamoto, S., and Hayaishi, O. (1979) J. Biol. Chem. 254, 829-836
44. Wu, G., Wei, C., Kulmacz, R. J., Osawa, Y., and Tsai, A. L. (1999) J. Biol. Chem. 274, 9231-9237
45. Rodriguez-Lopez, J. N., Hernandez-Ruiz, J., Garcia-Canovas, F., Thorneley, R. N., Acosta, M., and Arnao, M. B. (1997) J. Biol. Chem. 272, 5469-5476
46. Spolitak, T., Dawson, J. H., and Ballou, D. P. (2005) J. Biol. Chem. 280, 20300-20309
47. Kulmacz, R. J., and Lands, W. E. (1985) Prostaglandins 29, 175-190
48. Hemler, M. E., Graff, G., and Lands, W. E. (1978) Biochem. Biophys. Res. Commun. 85, 1325-1331
49. Hemler, M. E., and Lands, W. E. M. (1980) J. Biol. Chem. 255, 6253-6261
50. Landino, L. M., Crews, B. C., Gierse, J. K., Hauser, S. D., and Marnett, L. J. (1997) J. Biol. Chem. 272, 21565-21574
51. Dix, T. A., and Marnett, L. J. (1985) J. Biol. Chem. 260, 5351-5357
52. Brash, A. R., Hughes, M. A., Hawkins, D. J., Boeglin, W. E., Song, W. C., and Meijer, L. (1991) J. Biol. Chem. 266, 22926-22931
53. Adachi, S., Nagano, S., Ishimori, K., Watanabe, Y., Morishima, I., Egawa, T., Kitagawa, T., and Makino, R. (1993) Biochemistry 32, 241-252
54. Bach, R. D., Su, M.-D., and Schlegel, H. B. (1994) J. Am. Chem. Soc. 116, 5379-5391
55. Cremer, D. (1983) in The Chemistry of Peroxides (Patai, S., ed) Wiley Interscience, New York
56. Dawson, J. H. (1988) Science 240, 433-439
57. Poulos, T. (1996) J. Biol. Inorg. Biochem. 1, 356-359
58. Yu, Y., Fan, J., Chen, X. S., Wang, D., Klein-Szanto, A. J., Campbell, R. L., FitzGerald, G. A., and Funk, C. D. (2006) Nat. Med. 12, 699-704
59. Smith, W. L., and Lands, W. E. (1972) Biochemistry 11, 3276-3285
60. Kulmacz, R. J., and Lands, W. E. (1983) Prostaglandins 25, 531-540
61. Capdevila, J. H., Morrow, J. D., Belosludtsev, Y. Y., Beauchamp, D. R., DuBois, R. N., and Falck, J. R. (1995) Biochemistry 34, 3325-3337
62. Kulmacz, R. J., and Wang, L. H. (1995) J. Biol. Chem. 270, 24019-24023
63. Chen, W., Pawelek, T. R., and Kulmacz, R. J. (1999) J. Biol. Chem. 274, 20301-20306
64. Kulmacz, R. J. (2005) Biochem. Biophys. Res. Commun. 338, 25-33
65. Swinney, D. C., Mak, A. Y., Barnett, J., and Ramesha, C. S. (1997) J. Biol. Chem. 272, 12393-12398
66. Landino, L. M., Crews, B. C., Timmons, M. D., Morrow, J. D., and Marnett, L. J. (1996) Proc. Natl. Acad. Sci. U. S. A. 93, 15069-15074
67. Girotti, A. W. (1998) J. Lipid Res. 39, 1529-1542
68. Staniek, K., and Nohl, H. (2000) Biochim. Biophys. Acta 1460, 268-275
69. St-Pierre, J., Buckingham, J. A., Roebuck, S. J., and Brand, M. D. (2002) J. Biol. Chem. 277, 44784-44790
70. Hwang, C., Sinskey, A. J., and Lodish, H. F. (1992) Science 257, 1496-1502
71. Kurumbail, R. G., Stevens, A. M., Gierse, J. K., McDonald, J. J., Stegeman, R. A., Pak, J. Y., Gildehaus, D., Miyashiro, J. M., Penning, T. D., Seibert, K., Isakson, P. C., and Stallings, W. C. (1996) Nature 384, 644-648
72. Luong, C., Miller, A., Barnett, J., Chow, J., Ramesha, C., and Browner, M. F. (1996) Nat. Struct. Biol. 3, 927-933
73. Kulmacz, R. J., Pendleton, R. B., and Lands, W. E. (1994) J. Biol. Chem. 269, 5527-5536
74. Tsai, A. L., Palmer, G., and Kulmacz, R. J. (1992) J. Biol. Chem. 267, 17753-17759
75. Kulmacz, R. J., Ren, Y., Tsai, A. L., and Palmer, G. (1990) Biochemistry 29, 8760-8771
76. Bakovic, M., and Dunford, H. B. (1996) J. Biol. Chem. 271, 2048-2056
77. Hsi, L. C., Hoganson, C. W., Babcock, G. T., Garavito, R. M., and Smith, W. L. (1995) Biochem. Biophys. Res. Commun. 207, 652-660
78. Svistunenko, D. A. (2005) Biochim. Biophys. Acta 1707, 127-155
79. Kelley, S. O., and Barton, J. K. (1999) Met. Ions Biol. Syst. 36, 211-249
80. Witting, P. K., and Mauk, A. G. (2001) J. Biol. Chem. 276, 16540-16547
81. Kulmacz, R. J. (1986) Arch. Biochem. Biophys. 249, 273-285