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Volumn 304, Issue 2, 2003, Pages 589-595

Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes

Author keywords

[No Author keywords available]

Indexed keywords

12 HYDROXYICOSATETRAENOIC ACID; HYDROPEROXIDE; ICOSAPENTAENOIC ACID; PARACETAMOL; PROSTAGLANDIN SYNTHASE; PROTOPORPHYRIN; SALICYLIC ACID; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; ISOENZYME; LIPID PEROXIDE; PEROXIDASE;

EID: 0037310693     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.102.042853     Document Type: Article
Times cited : (30)

References (34)
  • 1
    • 0035861896 scopus 로고    scopus 로고
    • Sodium salicylate enhances the expression of cyclooxygenase-2 in endotoxin-stimulated human mononuclear cells
    • Amann R, Egger T, Schuligoi R, Heinemann A, and Peskar BA (2001) Sodium salicylate enhances the expression of cyclooxygenase-2 in endotoxin-stimulated human mononuclear cells. Eur J Pharmacol 433:129-134.
    • (2001) Eur J Pharmacol , vol.433 , pp. 129-134
    • Amann, R.1    Egger, T.2    Schuligoi, R.3    Heinemann, A.4    Peskar, B.A.5
  • 2
    • 0034827525 scopus 로고    scopus 로고
    • Antipyretics: Mechanisms of action and clinical use in fever suppression
    • Aronoff DM and Neilson EG (2001) Antipyretics: mechanisms of action and clinical use in fever suppression. Am J Med 111:304-315.
    • (2001) Am J Med , vol.111 , pp. 304-315
    • Aronoff, D.M.1    Neilson, E.G.2
  • 3
    • 0037076347 scopus 로고    scopus 로고
    • Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H2 synthases
    • Boutaud O, Aronoff DM, Richardson JH, Marnett LJ, and Oates JA (2002) Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H2 synthases. Proc Natl Acad Sci 99:7130-7135.
    • (2002) Proc Natl Acad Sci , vol.99 , pp. 7130-7135
    • Boutaud, O.1    Aronoff, D.M.2    Richardson, J.H.3    Marnett, L.J.4    Oates, J.A.5
  • 4
    • 0020501684 scopus 로고
    • Sodium salicylate interferes with the inhibitory effects of aspirin and indomethacin on human platelets
    • Dahl ML, Puustinen T, and Uotila P (1983) Sodium salicylate interferes with the inhibitory effects of aspirin and indomethacin on human platelets. Prostaglandins Leukot Med 12:21-28.
    • (1983) Prostaglandins Leukot Med , vol.12 , pp. 21-28
    • Dahl, M.L.1    Puustinen, T.2    Uotila, P.3
  • 5
    • 0023839666 scopus 로고
    • Higher oxidation states of prostaglandin H synthase. Rapid electronic spectroscopy detected two spectral intermediates during the peroxidase reaction with prostaglandin G2
    • Dietz R, Nastainczyk W, and Ruf HH (1988) Higher oxidation states of prostaglandin H synthase. Rapid electronic spectroscopy detected two spectral intermediates during the peroxidase reaction with prostaglandin G2. Eur J Biochem 171:321-328.
    • (1988) Eur J Biochem , vol.171 , pp. 321-328
    • Dietz, R.1    Nastainczyk, W.2    Ruf, H.H.3
  • 6
    • 0035197732 scopus 로고    scopus 로고
    • Sodium salicylate inhibits prostaglandin formation without affecting the induction of cyclooxygenase-2 by bacterial lipopolysaccharide in vivo
    • Giuliano F, Mitchell JA and Warner TD (2001) Sodium salicylate inhibits prostaglandin formation without affecting the induction of cyclooxygenase-2 by bacterial lipopolysaccharide in vivo. J Pharmacol Exp Ther 299:894-900.
    • (2001) J Pharmacol Exp Ther , vol.299 , pp. 894-900
    • Giuliano, F.1    Mitchell, J.A.2    Warner, T.D.3
  • 7
    • 0020373256 scopus 로고
    • Modification of anti-inflammatory drug effectiveness by ambient lipid peroxides
    • Hanel AM and Lands WE (1982) Modification of anti-inflammatory drug effectiveness by ambient lipid peroxides. Biochem Pharmacol 31:3307-3311.
    • (1982) Biochem Pharmacol , vol.31 , pp. 3307-3311
    • Hanel, A.M.1    Lands, W.E.2
  • 8
    • 0018240486 scopus 로고
    • Accelerative autoactivation of prostaglandin biosynthesis by PGG2
    • Hemler ME, Graff G, and Lands WE (1978) Accelerative autoactivation of prostaglandin biosynthesis by PGG2. Biochem Biophys Res Commun 85:1325-1331.
    • (1978) Biochem Biophys Res Commun , vol.85 , pp. 1325-1331
    • Hemler, M.E.1    Graff, G.2    Lands, W.E.3
  • 9
    • 0018976320 scopus 로고
    • Evidence for a peroxide-initiated free radical mechanism of prostaglandin biosynthesis
    • Hemler ME and Lands WE (1980) Evidence for a peroxide-initiated free radical mechanism of prostaglandin biosynthesis. J Biol Chem 255:6253-6261.
    • (1980) J Biol Chem , vol.255 , pp. 6253-6261
    • Hemler, M.E.1    Lands, W.E.2
  • 10
    • 0033015418 scopus 로고    scopus 로고
    • Salicylate promotes myeloperoxidase-initiated LDL oxidation: Antagonization by its metabolite gentisic acid
    • Hermann M, Kapiotis S, Hofbauer R, Seelos C, Held I, and Gmeiner B (1999) Salicylate promotes myeloperoxidase-initiated LDL oxidation: antagonization by its metabolite gentisic acid. Free Radic Biol Med 26:1253-1260.
    • (1999) Free Radic Biol Med , vol.26 , pp. 1253-1260
    • Hermann, M.1    Kapiotis, S.2    Hofbauer, R.3    Seelos, C.4    Held, I.5    Gmeiner, B.6
  • 11
    • 0033943280 scopus 로고    scopus 로고
    • Salicylate metabolites inhibit cyclooxygenase-2-dependent prostaglandin E(2) synthesis in murine macrophages
    • Hinz B, Kraus V, Pahl A, and Brune K (2000) Salicylate metabolites inhibit cyclooxygenase-2-dependent prostaglandin E(2) synthesis in murine macrophages. Biochem Biophys Res Commun 274:197-202.
    • (2000) Biochem Biophys Res Commun , vol.274 , pp. 197-202
    • Hinz, B.1    Kraus, V.2    Pahl, A.3    Brune, K.4
  • 12
    • 12944309750 scopus 로고    scopus 로고
    • Tyrosine-385 is critical for acetylation of cyclooxygenase-2 by aspirin
    • Hochgesang GP, Rowlinson SW, and Marnett LJ (2000) Tyrosine-385 is critical for acetylation of cyclooxygenase-2 by aspirin. J Am Chem Soc 122:6514-6515.
    • (2000) J Am Chem Soc , vol.122 , pp. 6514-6515
    • Hochgesang, G.P.1    Rowlinson, S.W.2    Marnett, L.J.3
  • 13
    • 0019510895 scopus 로고
    • Multiple sites on prostaglandin cyclooxygenase are determinants in the action of nonsteroidal antiinflammatory agents
    • Humes JL, Winter CA, Sadowski SJ and Kuehl FA Jr (1981) Multiple sites on prostaglandin cyclooxygenase are determinants in the action of nonsteroidal antiinflammatory agents. Proc Natl Acad Sci USA 78:2053-2056.
    • (1981) Proc Natl Acad Sci USA , vol.78 , pp. 2053-2056
    • Humes, J.L.1    Winter, C.A.2    Sadowski, S.J.3    Kuehl F.A., Jr.4
  • 14
    • 0023839665 scopus 로고
    • Higher oxidation states of prostaglandin H synthase. EPR study of a transient tyrosyl radical in the enzyme during the peroxidase reaction
    • Karthein R, Dietz R, Nastainczyk W, and Ruf HH (1988) Higher oxidation states of prostaglandin H synthase. EPR study of a transient tyrosyl radical in the enzyme during the peroxidase reaction. Eur J Biochem 171:313-320.
    • (1988) Eur J Biochem , vol.171 , pp. 313-320
    • Karthein, R.1    Dietz, R.2    Nastainczyk, W.3    Ruf, H.H.4
  • 15
    • 0029877041 scopus 로고    scopus 로고
    • Mechanism of hydroperoxide reduction by mangano-prostaglandin endoperoxide synthase
    • Landino LM and Marnett LJ (1996) Mechanism of hydroperoxide reduction by mangano-prostaglandin endoperoxide synthase. Biochemistry 35:2637-2643.
    • (1996) Biochemistry , vol.35 , pp. 2637-2643
    • Landino, L.M.1    Marnett, L.J.2
  • 16
    • 0029056992 scopus 로고
    • The structural basis of aspirin activity inferred from the crystal structure of inactivated prostaglandin H2 synthase
    • Loll PJ, Picot D, and Garavito RM (1995) The structural basis of aspirin activity inferred from the crystal structure of inactivated prostaglandin H2 synthase. Nat Struct Biol 2:637-643.
    • (1995) Nat Struct Biol , vol.2 , pp. 637-643
    • Loll, P.J.1    Picot, D.2    Garavito, R.M.3
  • 17
    • 0023644747 scopus 로고
    • Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities
    • Markey CM, Alward A, Weller PE, and Marnett LJ (1987) Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities. J Biol Chem 262:6266-6279.
    • (1987) J Biol Chem , vol.262 , pp. 6266-6279
    • Markey, C.M.1    Alward, A.2    Weller, P.E.3    Marnett, L.J.4
  • 18
    • 0033776880 scopus 로고    scopus 로고
    • Cyclooxygenase mechanisms
    • Marnett LJ (2000) Cyclooxygenase mechanisms. Curr Opin Chem Biol 4:545-552.
    • (2000) Curr Opin Chem Biol , vol.4 , pp. 545-552
    • Marnett, L.J.1
  • 19
    • 0021738403 scopus 로고
    • Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom
    • Marnett LJ, Siedlik PH, Ochs RC, Pagels WR, Das M, Honn KV, Warnock RH, Tainer BE, and Eling TE (1984) Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom. Mol Pharmacol 26:328-335.
    • (1984) Mol Pharmacol , vol.26 , pp. 328-335
    • Marnett, L.J.1    Siedlik, P.H.2    Ochs, R.C.3    Pagels, W.R.4    Das, M.5    Honn, K.V.6    Warnock, R.H.7    Tainer, B.E.8    Eling, T.E.9
  • 20
    • 0018889101 scopus 로고
    • Salicylate reverses in vitro aspirin inhibition of rat platelet and vascular prostaglandin generation
    • Merino J, Livio M, Rajtar G, and de Gaetano G (1980) Salicylate reverses in vitro aspirin inhibition of rat platelet and vascular prostaglandin generation. Biochem Pharmacol 29:1093-1096.
    • (1980) Biochem Pharmacol , vol.29 , pp. 1093-1096
    • Merino, J.1    Livio, M.2    Rajtar, G.3    De Gaetano, G.4
  • 21
    • 0027146692 scopus 로고
    • Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase
    • Mitchell JA, Akarasereenont P, Thiemermann C, Flower RJ, and Vane JR (1994) Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci USA 90:11693-11697.
    • (1994) Proc Natl Acad Sci USA , vol.90 , pp. 11693-11697
    • Mitchell, J.A.1    Akarasereenont, P.2    Thiemermann, C.3    Flower, R.J.4    Vane, J.R.5
  • 22
    • 0030976878 scopus 로고    scopus 로고
    • Sodium salicylate inhibits cyclo-oxygenase-2 activity independently of transcription factor (nuclear factor κB) activation: Role of arachidonic acid
    • Mitchell JA, Saunders M, Barnes PJ, Newton R, and Belvisi MG (1997) Sodium salicylate inhibits cyclo-oxygenase-2 activity independently of transcription factor (nuclear factor κB) activation: role of arachidonic acid. Mol Pharmacol 51:907-912.
    • (1997) Mol Pharmacol , vol.51 , pp. 907-912
    • Mitchell, J.A.1    Saunders, M.2    Barnes, P.J.3    Newton, R.4    Belvisi, M.G.5
  • 23
    • 0025182574 scopus 로고
    • Preparation and proteolytic cleavage of apoprostaglandin endoperoxide synthase
    • Odenwaller R, Chen YN, and Marnett LJ (1990) Preparation and proteolytic cleavage of apoprostaglandin endoperoxide synthase. Methods Enzymol 187:479-485.
    • (1990) Methods Enzymol , vol.187 , pp. 479-485
    • Odenwaller, R.1    Chen, Y.N.2    Marnett, L.J.3
  • 24
    • 0026629281 scopus 로고
    • Detection of a higher oxidation state of manganese-prostaglandin endoperoxide synthase
    • Odenwaller R, Maddipati KR, and Marnett LJ (1992) Detection of a higher oxidation state of manganese-prostaglandin endoperoxide synthase. J Biol Chem 267:13863-13869.
    • (1992) J Biol Chem , vol.267 , pp. 13863-13869
    • Odenwaller, R.1    Maddipati, K.R.2    Marnett, L.J.3
  • 25
    • 0035866579 scopus 로고    scopus 로고
    • Mechanism of acetaminophen inhibition of cyclooxygenase isoforms
    • Ouellet M and Percival MD (2001) Mechanism of acetaminophen inhibition of cyclooxygenase isoforms. Arch Biochem Biophys 387:273-280.
    • (2001) Arch Biochem Biophys , vol.387 , pp. 273-280
    • Ouellet, M.1    Percival, M.D.2
  • 26
    • 0030733305 scopus 로고    scopus 로고
    • Comparison of the cyclooxygenase-1 inhibitory properties of nonsteroidal antiinflammatory drugs (NSAIDs) and selective COX-2 inhibitors, using sensitive microsomal and platelet assays
    • Riendeau D, Charleson S, Cromlish W, Mancini JA, Wong E, and Guay J (1997) Comparison of the cyclooxygenase-1 inhibitory properties of nonsteroidal antiinflammatory drugs (NSAIDs) and selective COX-2 inhibitors, using sensitive microsomal and platelet assays. Can J Physiol Pharmacol 75:1088-1095.
    • (1997) Can J Physiol Pharmacol , vol.75 , pp. 1088-1095
    • Riendeau, D.1    Charleson, S.2    Cromlish, W.3    Mancini, J.A.4    Wong, E.5    Guay, J.6
  • 27
    • 0028152749 scopus 로고
    • Salicylamide reverses the aspirin-antagonistic effect of salicylic acid on rat platelet cyclooxygenase
    • Rizk M and Abdel-Rahman MS (1994) Salicylamide reverses the aspirin-antagonistic effect of salicylic acid on rat platelet cyclooxygenase. Prostaglandins Leukot Essent Fatty Acids 51:363-367.
    • (1994) Prostaglandins Leukot Essent Fatty Acids , vol.51 , pp. 363-367
    • Rizk, M.1    Abdel-Rahman, M.S.2
  • 28
    • 0033551732 scopus 로고    scopus 로고
    • The binding of arachidonic acid in the cyclooxygenase active site of mouse prostaglandin endoperoxide synthase-2 (COX-2). A putative L-shaped binding conformation utilizing the top channel region
    • Rowlinson SW, Crews BC, Lanzo CA, and Marnett LJ (1999) The binding of arachidonic acid in the cyclooxygenase active site of mouse prostaglandin endoperoxide synthase-2 (COX-2). A putative L-shaped binding conformation utilizing the top channel region. J Biol Chem 274:23305-23310.
    • (1999) J Biol Chem , vol.274 , pp. 23305-23310
    • Rowlinson, S.W.1    Crews, B.C.2    Lanzo, C.A.3    Marnett, L.J.4
  • 29
    • 0015581011 scopus 로고
    • Generation of phenoxy radicals by methemoglobinhydrogen peroxide studies by electron paramagnetic resonance
    • Shiga T and Imaizumi K (1973) Generation of phenoxy radicals by methemoglobinhydrogen peroxide studies by electron paramagnetic resonance. Arch Biochem Biophys 154:540-547.
    • (1973) Arch Biochem Biophys , vol.154 , pp. 540-547
    • Shiga, T.1    Imaizumi, K.2
  • 30
    • 0016616098 scopus 로고
    • Electron spin resonance study on peroxidase and oxidase reactions of horseradish peroxidase and methemoglobin
    • Shiga T and Imaizumi K (1975) Electron spin resonance study on peroxidase and oxidase reactions of horseradish peroxidase and methemoglobin. Arch Biochem Biophys 167:469-479.
    • (1975) Arch Biochem Biophys , vol.167 , pp. 469-479
    • Shiga, T.1    Imaizumi, K.2
  • 31
    • 0034816925 scopus 로고    scopus 로고
    • Cyclooxygenase-independent actions of cyclooxygenase inhibitors
    • Tegeder I, Pfeilschifter J, and Geisslinger G (2001) Cyclooxygenase-independent actions of cyclooxygenase inhibitors. FASEB J 15:2057-2072.
    • (2001) FASEB J , vol.15 , pp. 2057-2072
    • Tegeder, I.1    Pfeilschifter, J.2    Geisslinger, G.3
  • 32
    • 0015237292 scopus 로고
    • Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs
    • Vane JR (1971) Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol 231:232-235.
    • (1971) Nat New Biol , vol.231 , pp. 232-235
    • Vane, J.R.1
  • 33
    • 0018198404 scopus 로고
    • The inhibition of cyclo-oxygenase of rabbit platelets by aspirin is prevented by salicylic acid and by phenanthrolines
    • Vargaftig BB (1978) The inhibition of cyclo-oxygenase of rabbit platelets by aspirin is prevented by salicylic acid and by phenanthrolines. Eur J Pharmacol 50:231-241.
    • (1978) Eur J Pharmacol , vol.50 , pp. 231-241
    • Vargaftig, B.B.1


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