The structures of prostaglandin endoperoxide H synthases-1 and -2

Smith, 2000, Cyclooxygenases: structural, cellular, and molecular biology, Annu. Rev. Biochem., 69, 145, 10.1146/annurev.biochem.69.1.145

Smith, 1996, Prostaglandin endoperoxide H synthases (cyclooxygenses)-1 and -2, J. Biol. Chem., 271, 33157, 10.1074/jbc.271.52.33157

Marnett, 1999, Arachidonic acid oxygenation by COX-1 and COX-2, J. Biol. Chem., 274, 22903, 10.1074/jbc.274.33.22903

Hla, 1999, Cyclooxygenase-1 and -2 isoenzymes, Int. J. Biochem. Cell. Biol., 31, 551, 10.1016/S1357-2725(98)00152-6

Smith WL, Borgeat P, Fitzpatrick FA. The eicosanoids: cyclooxygenase, lipoxygenase, and epoxygenase pathways. In: Vance DE, Vance J, editors. Biochemistry of lipids, lipoproteins and membranes. New York: Elsevier, 1991. p. 297–325.

Herschman, 1996, Prostaglandin synthase 2, Biochim. Biophys. Acta., 1299, 125, 10.1016/0005-2760(95)00194-8

Morita, 1995, Different intracellular locations for prostaglandin endoperoxide H synthase-1 and -2, J. Biol. Chem., 270, 10902, 10.1074/jbc.270.18.10902

Spencer, 1999, The membrane binding domains of prostaglandin endoperoxide H synthases 1 and 2. Peptide mapping and mutational analysis, J. Biol. Chem., 274, 32936, 10.1074/jbc.274.46.32936

Patrignani, 1994, Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases, J. Pharmacol. Exp. Ther., 271, 1705

Patrono, 1994, Aspirin as an antiplatelet drug, N. Engl. J. Med., 330, 1287, 10.1056/NEJM199405053301808

Crofford, 2000, Basic biology and clinical application of specific cyclooxygenase-2 inhibitors, Arthritis Rheum., 43, 4, 10.1002/1529-0131(200001)43:1<4::AID-ANR2>3.0.CO;2-V

Levy, 1997, Prostaglandin H synthases, nonsteroidal anti-inflammatory drugs, and colon cancer, FASEB J., 11, 234, 10.1096/fasebj.11.4.9068612

Williams, 1999, The role of cyclooxygenases in inflammation, cancer, and development, Oncogene, 18, 7908, 10.1038/sj.onc.1203286

McGeer, 1999, Inflammation of the brain in Alzheimer’s disease: implications for therapy, J. Leukoc. Biol., 65, 409, 10.1002/jlb.65.4.409

Smythies, 1996, On the function of neuromelanin, Proc. R. Soc. Lond., 263, 487, 10.1098/rspb.1996.0073

Smith WL, DeWitt DL. In: Dixon FJ, editor. Advances in immunology, vol. 62. San Diego, CA: Academic Press, 1996. p. 167–215.

Otto, 1996, Photolabeling of prostaglandin endoperoxide H synthase-1 with 3-trifluoro-3-m-[125I]iodophenyl)diazirine as a probe of membrane association and the cyclooxygenase active site, J. Biol. Chem., 271, 9906, 10.1074/jbc.271.17.9906

Otto, 1993, N-glycosylation of prostaglandin endoperoxide synthases-1 and -2 and their orientations in the endoplasmic reticulum, J. Biol. Chem., 268, 18234, 10.1016/S0021-9258(17)46835-9

Smith, 2000, Purification and characterization of the human recombinant histidine-tagged prostaglandin H endoperoxide synthases-1 and -2, Arch. Biochem. Biophys., 374, 195, 10.1006/abbi.1999.1659

Barnett, 1994, Purification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and expressed in the baculovirus system, Biochim. Biophys. Acta., 1209, 130, 10.1016/0167-4838(94)90148-1

Gierse, 1995, Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase, Biochem. J., 305, 479, 10.1042/bj3050479

van der Ouderaa, 1977, Purification and characterization of prostaglandin endoperoxide synthase from sheep vesicular glands, Biochim. Biophys. Acta, 487, 315, 10.1016/0005-2760(77)90008-X

Malkowski, 2000, The formation of stable fatty acid substrate complexes in prostaglandin H2 synthase-1, Arch. Biochem. Biophys., 380, 39, 10.1006/abbi.2000.1906

Kulmacz RJ, Lands WEM. Cyclo-oxygenase: measurement, purification and properties. In: Benedetto C, McDonald-Gibson RG, Nigan S, Slater TF, editors. Prostaglandin and related substances: a practical approach. Washington DC: IRL Press, 1987. p. 209–27.

Ogino, 1978, Prostaglandin endoperoxide synthetases from bovine vesicular gland microsomes, J. Biol. Chem., 253, 5061, 10.1016/S0021-9258(17)34657-4

Tsai, 1998, Structural characterization of arachidonyl radicals formed by prostaglandin H synthase-2 and prostaglandin H synthase-1 reconstituted with mangano protoporphyrin IX, J. Biol. Chem., 273, 3888, 10.1074/jbc.273.7.3888

Tsai, 1997, Comparison of peroxidase reaction mechanisms of prostaglandin H synthase-1 containing heme and mangano protoporphyrin IX, J. Biol. Chem., 272, 8885, 10.1074/jbc.272.14.8885

Picot, 1994, The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1, Nature, 367, 243, 10.1038/367243a0

Luong, 1996, Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2, Nat. Struct. Biol., 3, 927, 10.1038/nsb1196-927

Kurumbail, 1996, Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents, Nature (London), 384, 644, 10.1038/384644a0

Malkowski, 2000, The X-ray structure of prostaglandin endoperoxide H synthase-1 complexed with arachidonic acid, Science, 289, 1933, 10.1126/science.289.5486.1933

Thuresson, 2001, Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma-linolenic acid with prostaglandin endoperoxide H synthases, J. Biol. Chem., 276, 10358, 10.1074/jbc.M009378200

Malkowski, 2001, Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1, J. Biol. Chem., 276, 37547, 10.1074/jbc.M105982200

Kiefer, 2000, Structural insights into the stereochemistry of the cyclooxygenase reaction, Nature, 405, 97, 10.1038/35011103

Xiao, 1998, Comparison of prostaglandin H synthase-1 and -2 structural stabilities, J. Biol. Chem., 273, 6801, 10.1074/jbc.273.12.6801

Campbell, 1993, Epidermal growth factor-like modules, Curr. Opin. Struct. Biol., 3, 385, 10.1016/S0959-440X(05)80111-3

Garavito, 1994, Prostaglandin H synthase, Curr. Opin. Struct. Biol., 4, 529, 10.1016/S0959-440X(94)90215-1

Picot D, Garavito R. Prostaglandin H synthase: implications for membrane structure. FEBS Lett 1994;346:21–5.

Li, 1998, The membrane association sequences of the prostaglandin endoperoxide synthases-1 and -2 isozymes, J. Biol. Chem., 273, 29830, 10.1074/jbc.273.45.29830

Magnusson RP. Thyroid peroxidase. In: Everse J, Everse KE, Grisham MB, editors. Peroxidases in chemistry and biology, vol. 1. Boca Raton: CRC Press, 1990. p. 199-219.

Nina, 2000, Anchoring of a monotopic membrane protein: the binding of prostaglandin H2 synthase-1 to the surface of a phospholipid bilayer, Eur. Biophys. J., 29, 439, 10.1007/PL00006649

Loll, 1995, The structural basis of aspirin activity inferred from the crystal structure of inactivated prostaglandin H2 synthase, Nat. Struct. Biol., 2, 637, 10.1038/nsb0895-637

Loll, 1996, The synthesis and use of iodinated non-steroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site, Biochemistry, 35, 7330, 10.1021/bi952776w

Poulos TL, Fenna RE. Peroxidases: structure, function and engineering. In: Sigal H, Sigel A, editors. Metal ions in biological systems. New York: Marcel Dekker, 1994. p. 163–99.

Seibold, 2000, Peroxidase activity in prostaglandin endoperoxide H synthase-1 occurs with a neutral histidine proximal heme ligand, Biochemistry, 39, 6616, 10.1021/bi0002333

Gajhede, 1997, Crystal structure of horseradish peroxidase C at 2.15 Å resolution, Nat. Struct. Biol., 4, 1032, 10.1038/nsb1297-1032

Landino, 1997, Mutational analysis of the role of the distal histidine and glutamine residues of prostaglandin-endoperoxide synthase-2 in peroxidase catalysis, hydroperoxide reduction, and cyclooxygenase activation, J. Biol. Chem., 272, 21565, 10.1074/jbc.272.34.21565

Shimokawa, 1991, Essential histidines of prostaglandin endoperoxide synthase. His-309 is involved in heme binding, J. Biol. Chem., 266, 6168, 10.1016/S0021-9258(18)38099-2

Lopez-Garriga, 1990, Metal-ligand vibrations of cyanoferric myeloperoxidase and cyanoferric horseradish peroxidase: evidence for a constrained heme pocket in myeloperoxidase, Biochemistry, 29, 9387, 10.1021/bi00492a012

Zeng J, Fenna RE. X-ray crystal structure of canine myeloperoxidase at 3 Å resolution. J Molec Biol 1992;226:185–207.

Smith WL, Marnett LJ. Prostaglandin endoperoxide synthases. In: Sigal H, Sigel A, editors. Metal ions in biological systems. New York: Marcel Dekker, 1994. p. 163–99.

Garavito, 1999, The cyclooxygenase isoforms: structural insights into the conversion of arachidonic acid to prostaglandins, Biochim. Biophys. Acta, 1441, 278, 10.1016/S1388-1981(99)00147-X

Bhattacharyya, 1996, Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2-phenylproprionic acid inhibitors to the cyclooxygenase active site of ovine prostaglandin endoperoxide H synthase-1, J. Biol. Chem., 271, 2179, 10.1074/jbc.271.4.2179

Rieke, 1999, The role of arginine 120 of human prostaglandin endoperoxide H synthase-2 in the interaction with fatty acid substrates and inhibitors, J. Biol. Chem., 274, 17109, 10.1074/jbc.274.24.17109

DeWitt, 1990, The aspirin and heme-binding sites of ovine and murine prostaglandin endoperoxide synthases, J. Biol. Chem., 265, 5192, 10.1016/S0021-9258(19)34105-5

Marnett, 2000, Cyclooxygenase mechanisms, Curr. Opin. Chem. Biol., 4, 545, 10.1016/S1367-5931(00)00130-7

Schneider, 2002, Control of prostaglandin stereochemistry at the 15-carbon by cyclooxygenases-1 and -2: a critical role for Serine-530 and Valine-349, J. Biol. Chem., 277, 478, 10.1074/jbc.M107471200

Thuresson, 2001, Prostaglandin endoperoxide H synthase-1: the functions of cyclooxygenase active site residues in the binding, positioning, and oxygenation of arachidonic acid, J. Biol. Chem., 276, 10347, 10.1074/jbc.M009377200

Thuresson, 2000, Different catalytically competent arrangements of arachidonic acid within the cyclooxygenase active site of prostaglandin endoperoxide H synthase-1 lead to the formation of different oxygenated products, J. Biol. Chem., 275, 8501, 10.1074/jbc.275.12.8501

Xiao, 1997, Analysis of hydroperoxide-induced tyrosyl radicals and lipoxygenase activity in aspirin-treated human prostaglandin H synthase-2, Biochemistry, 36, 1836, 10.1021/bi962476u

Laneuville, 1995, Fatty acid substrate specificities of human prostaglandin-endoperoxide H synthase-1 and -2. Formation of 12-hydroxy-(9Z, 13E/Z, 15Z)-octadecatrienoic acids from alpha-linolenic acid, J. Biol. Chem., 270, 19330, 10.1074/jbc.270.33.19330

Rowlinson, 1999, The binding of arachidonic acid in the cyclooxygenase active site of mouse prostaglandin endoperoxide synthase-2 (COX-2), J. Biol. Chem., 274, 23305, 10.1074/jbc.274.33.23305

Mancini, 1995, Arginine 120 of prostaglandin G/H synthase-1 is required for the inhibition by nonsteroidal anti-inflammatory drugs containing a carboxylic acid moiety, J. Biol. Chem., 270, 29372, 10.1074/jbc.270.49.29372

Greig, 1997, The interaction of arginine 106 of human prostaglandin G/H synthase-2 with inhibitors is not a universal component of inhibition mediated by nonsteroidal anti-inflammatory drugs, Mol. Pharmacol., 52, 829, 10.1124/mol.52.5.829

So, 1998, The dynamics of prostaglandin H synthases. Studies with prostaglandin H synthase-2 Y355F unmask mechanisms of time-dependent inhibition and allosteric activation, J. Biol. Chem., 273, 5801, 10.1074/jbc.273.10.5801

Shimokawa, 1992, Prostaglandin endoperoxide synthase: the aspirin acetylation region, J. Biol. Chem., 267, 12387, 10.1016/S0021-9258(19)49852-9

Lecomte, 1994, Acetylation of human prostaglandin endoperoxide synthase-2 (cyclooxygenase-2) by aspirin, J. Biol. Chem., 269, 13207, 10.1016/S0021-9258(17)36820-5

Mancini JA, O’Neill GP, Bayly C, Vickers PJ. Mutation of serine-516 in human prostaglandin G/H synthase-2 to methionine or aspirin acetylation of this residue stimulates 15R-HETE synthesis. FEBS Letters 1994;342:33–7.

Schneider, 2000, Stereospecificity of hydrogen abstraction in the conversion of arachidonic acid to 15R-HETE by aspirin-treated cyclooxygenase-2. Implications for the alignment of substrate in the active site, J. Biol. Chem., 275, 4743, 10.1074/jbc.275.7.4743

Hamberg, 1967, J. Biol. Chem., 242, 5336, 10.1016/S0021-9258(18)99433-0

Munroe, 1995, Turning down the heat: new routes to inhibition of inflammatory signaling by prostaglandin H2 synthases, Chem. Biol., 2, 343, 10.1016/1074-5521(95)90212-0

DeWitt, 1999, COX-2 selective inhibitors: the new super aspirins, Mol. Pharmacol., 4, 625

Rome LH, Lands WEM. Structural requirements for time-dependent inhibition of prostaglandin biosynthesis by anti-inflammatory drugs. Proc Natl Acad Sci USA 1975;72:4863–5.

Gierse, 1996, A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of COX-2 inhibitors, J. Biol. Chem., 271, 15810, 10.1074/jbc.271.26.15810

Guo, 1996, Role of Val509 in time-dependent inhibition of human prostaglandin H synthase-2 cyclooxygenase activity by isoform-selective agents, J. Biol. Chem., 271, 19134, 10.1074/jbc.271.32.19134

Wong, 1997, Conversion of prostaglandin G/H synthase-1 into an enzyme sensitive to PGHS-2-selective inhibitors by a double His513 → Arg and Ile523 → Val mutation, J. Biol. Chem., 272, 9280, 10.1074/jbc.272.14.9280

Chen, 1987, Controlled tryptic digestion of prostaglandin H synthase. Characterization of protein fragments and enhanced rate of proteolysis of oxidatively inactivated enzyme, J. Biol. Chem., 262, 16892, 10.1016/S0021-9258(18)45467-1

Kulmacz, 1982, Protection of prostaglandin H synthase from trypsin upon binding of heme, Biochem. Biophys. Res. Commun., 104, 758, 10.1016/0006-291X(82)90702-1

Walker, 2001, A three-step kinetic mechanism for selective inhibition of cyclo-oxygenase-2 by diarylheterocyclic inhibitors, Biochem. J., 357, 709, 10.1042/bj3570709

Selinsky, 2001, Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations, Biochemistry, 40, 5172, 10.1021/bi010045s

Song, 1996, C-terminal Ser/Pro-Thr-Glu-Leu tetrapeptides of prostaglandin endoperoxide H synthases-1 and -2 target the enzymes to the endoplasmic reticulum, Arch. Biochem. Biophys., 334, 67, 10.1006/abbi.1996.0430

Kraulis, 1991, MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures, J. Appl. Crystogr., 24, 946, 10.1107/S0021889891004399

Merrit, 1994, Raster3D Version 2.0—a program for photorealistic molecular graphics, Acta Cryst., 50, 869

Evans, 1993, SETOR: hardware-lighted three-dimensional solid model representations of macromolecules, J Mol. Graph., 11, 134, 10.1016/0263-7855(93)87009-T