Phenylbutazone radicals inactivate creatine kinase

References

• Vane J.R. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nature New Biology 1971; 23: 232–235
   Google Scholar
• Garcia L.A., Jick H., Rodriguez. Risk of upper gastrointestinal bleeding and perforation associated with individual non-steroidal anti-inflammatory drugs. Lancet 1994; 343: 769–772
   PubMed Web of Science ®Google Scholar
• Hawkey C.J. Non-steroidal anti-inflammatory drug gastropathy: causes and treatment. Scandinavian Journal of Gastroenterology Suppl. 1996; 220: 124–127
   PubMedGoogle Scholar
• Masubuchi Y., Saito H., Horie T. Structural requirements for the hepatotoxicity of nonsteroidal anti-inflammatory drugs in isolated rat hepatocytes. Journal of Pharmacology and Experimental Therapeutics 1998; 287: 208–213
   PubMed Web of Science ®Google Scholar
• Masubuchi Y., Yamada S., Horie T. Possible mechanism of hepatocyte injury induced by diphenylamine and its structurally related nonsteroidal anti-inflammatory drugs. Journal of Pharmacology and Experimental Therapeutics 2000; 292: 982–987
   PubMed Web of Science ®Google Scholar
• Miyamoto T., Ogino N., Yamamoto S., Hayaishi O. Purification of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. Journal of Biological Chemistry 1976; 251: 2629–2636
   PubMed Web of Science ®Google Scholar
• Ohki S., Ogino N., Yamamoto S., Hayaishi O. Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. Journal of Biological Cheistry 1979; 254: 829–836
   PubMed Web of Science ®Google Scholar
• Van der Ouderaa F.J., Buytenhek M., Nugteren D.H., Van Dorp D.A. Purification and characterisation of prostaglandin endoperoxide synthetase from sheep vesicular glands. Biochimica et Biophysica Acta 1977; 487: 315–331
   PubMed Web of Science ®Google Scholar
• Hamberg M., Svensson J., Wakabayashi T., Samuelsson B. Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation. Proceedings of the National Academy of Sciences of the United States of America 1974; 71: 345–349
   PubMed Web of Science ®Google Scholar
• Marnett L.J., Wlodawer P., Samuelsson B. Co-oxygenation of organic substrates by the prostaglandin synthetase of sheep vesicular gland. Journal of Biological Chemistry 1975; 250: 8510–8517
   PubMed Web of Science ®Google Scholar
• Marnett L.J., Bienkowski M.J., Pagels W.R., Reed G.A. Mechanism of xenobiotic cooxygenation coupled to prostaglandin H2 biosynthesis. Advances in Prostaglandin Thromboxane Research 1980; 6: 149–151
   PubMedGoogle Scholar
• Markey C.M., Alward A., Weller P.E., Marnett L.J. Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities. Journal of Biological Chemistry 1987; 262: 6266–6279
   PubMed Web of Science ®Google Scholar
• Lakshmi V.M., Zenser T.V., Mattammal M.B., Davis B.B. Phenylbutazone peroxidatic metabolism and conjugation. Journal of Pharmacology and Experimental Therapeutics 1993; 266: 81–88
   PubMedGoogle Scholar
• Evans P.J., Cecchini R., Halliwell B B. Oxidative damage to lipids and alpha 1-antiproteinase by phenylbutazone in the presence of haem proteins: protection by ascorbic acid. Biochemical Pharmacology 1992; 44: 981–984
   PubMedGoogle Scholar
• Evans P.J., Akanmu D., Halliwell B. Promotion of oxidative damage to arachidonic acid and alpha 1-antiproteinase by anti-inflammatory drugs in the presence of the haem proteins myoglobin and cytochrome C. Biochemical Pharmacology 1994; 48: 2173–2179
   PubMed Web of Science ®Google Scholar
• Das D., Bandyopadhyay D., Banerjee R.K. Oxidative inactivation of gastric peroxidase by site-specific generation of hydroxyl radical and its role in stress-induced gastric ulceration. Free Radical Biology & Medicine 1998; 24: 460–469
   PubMed Web of Science ®Google Scholar
• Miura T., Muraoka S., Fujimoto Y. Effect of estrogens on the oxidative damage induced by ferrylmyoglobin. Journal of Steroid Biochemistry and Molecular Biology 1998; 67: 57–62
   PubMedGoogle Scholar
• Miura T., Muraoka S., Fujimoto Y. Inactivation of creatine kinase induced by dopa and dopamine in the presence of ferrylmyoglobin. Chemico-Biological Interactions 1999; 123: 51–61
   PubMed Web of Science ®Google Scholar
• Watts D.C. Creatine Kinase. The enzymes, P.D. Boyer. Academic Press, New York and London 1973; VII: 383–455, In
   Google Scholar
• Bonnichsen R.K., Brink N.G. Liver alcohol dehydrogenase. Methods in Enzymology 1955; 1: 495–496
   Web of Science ®Google Scholar
• Prinsze C., Dubbelman T.M., Van Steveninck J. Protein damage, induced by small amounts of photodynamically generated singlet oxygen or hydroxyl radicals. Biochimica et Biophysica Acta 1990; 1038: 152–157
   PubMed Web of Science ®Google Scholar
• Redinbaugh M.G., Turley R.B. Adaptation of the bicinchoninic acid protein assay for use with microtiter plates and sucrose gradient fractions. Analytical Biochemistry 1986; 153: 267–271
   PubMed Web of Science ®Google Scholar
• Ellman G.L. Tissue sulfhydryl groups. Archives of Biochemistry and Biophysics 1959; 82: 70–77
   PubMed Web of Science ®Google Scholar
• Vissers M.C., Winterbourn C.C. Oxidative damage to fibronectin. II. The effect of H2O2 and the hydroxyl radical. Archives of Biochemistry and Biophysics 1991; 285: 357–364
   PubMedGoogle Scholar
• Hughes M.F., Mason R.P., Eling T.E. Prostaglandin hydroperoxidase-dependent oxidation of phenylbutazone: relationship to inhibition of prostaglandin cyclooxygenase. Molecular Pharmacology 1988; 34: 186–193
   PubMed Web of Science ®Google Scholar
• Parij N., Neve J. Nonsteroidal antiinflammatory drugs interact with horseradish peroxidase in an in vitro assay system for hydrogen peroxide scavenging. European Journal of Pharmacology 1996; 311: 259–264
   PubMedGoogle Scholar
• Mottley C., Toy K., Mason R.P. Oxidation of thiol drugs and biochemicals by the lactoperoxidase/hydrogen peroxide system. Molecular Pharmacology 1987; 31: 417–421
   PubMed Web of Science ®Google Scholar
• Metodiewa D., Reszka K., Dunford H.B. Oxidation of the substituted catechols dihydroxyphenylalanine methyl ester and trihydroxyphenylalanine by lactoperoxidase and its compounds. Archives of Biochemistry and Biophysics 1989; 274: 601–608
   PubMed Web of Science ®Google Scholar
• Metodiewa D., Dunford H.B. Evidence for one-electron oxidation of benzylpenicillin G by lactoperoxidase compounds I and II. Biochemical and Biophysical Research Communications 1990; 169: 1211–1216
   PubMed Web of Science ®Google Scholar
• Duescher R.J., Elfarra A.A. 1,3-Butadiene oxidation by human myeloperoxidase. Role of chloride ion in catalysis of divergent pathways. Journal of Biological Chemistry 1992; 267: 19859–19865
   PubMed Web of Science ®Google Scholar
• Saeed S.A., Warren B.T. On the mode of action and biochemical properties of anti-inflammatory drugs. Biochemical Pharmacology 1973; 22: 1965–1969
   PubMedGoogle Scholar
• Kettle A.J., Winterbourn C.C. Mechanism of inhibition of myeloperoxidase by anti-inflammatory drugs. Biochemical Pharmacology 1991; 41: 1485–1492
   PubMed Web of Science ®Google Scholar