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Original Article

Oxidation of tetrahydrobiopterin by peroxynitrite or oxoferryl species occurs by a radical pathway

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Pages 709-721 | Received 12 Jul 2000, Published online: 07 Jul 2009

References

  • Kwon N.S., Nathan C.F., Stuehr D.J. Reduced biopterin as a cofactor in the generation of nitrogen oxides by murine macrophages. Journal of Biological Chemistry 1989; 264: 20496–20501
  • Schmidt K., Werner E.R., Mayer B., Wachter H., Kukovetz W.R. Tetrahydrobiopterin-dependent formation of endothelium-derived relaxing factor (nitric oxide) in aortic endothelial cells. Biochemical Journal 1992; 281: 297–300
  • Schaffner A., Blau N., Schneemann M., Steuer J., Edgell C.-J.S., Schoedon G. Tetrahydrobiopterin as another EDRF in man. Biochemical and Biophysical Research Communications 1994; 205: 516–523
  • Tayeh M.A., Marletta M.A. Macrophage oxidation of l-arginine to nitric oxide, nitrite, and nitrate. Tetrahydrobiopterin is required as a cofactor. Journal of Biological Chemistry 1989; 264: 19654–19658
  • Lazarus R.A., Dietrich R.F., Wallick D.E., Benkovic S.J. On the mechanism of action of phenylalanine hydroxylase. Biochemistry 1981; 20: 6834–6841
  • Nichol C.A., Smith G.K., Duch D.S. Biosynthesis and metabolism of tetrahydrobiopterin and molybdopterin. Annual Review of Biochemistry 1985; 54: 729–764
  • Depaepe V., Cuvelier L., Thöny B., Resibois A. Pterin-4 α-carbinolamine, dehydratase in rat brain. I. Patterns of co-localization with tyrosine hydroxylase. Brain Research. Molecular Brain Research 2000; 75: 76–88
  • Sawada M., Sugimoto T., Matsuura S., Nagatsu T. (6R)-tetrahydrobiopterin increases the activity of tryptophan hydroxylase in rat raphe slices. Journal of Neurochemistry 1986; 47: 1544–1547
  • Moran G.R., Derecskei-Kovacs A., Hillas P.J., Fitzpatrick P.F. On the catalytic mechanism of tryptophan hydroxylase. Journal of the American Chemical Society 2000; 122: 4535–4541
  • Thöny B., Auerbach G., Blau N. Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochemical Journal 2000; 347: 1–16
  • Pfeiffer S., Mayer B., Hemmens B. Nitric oxide: Chemical puzzles posed by a biological messenger. Angewandte Chemie International Edition 1999; 38: 1714–1731
  • Patterson W.R., Poulos T.L. Identification of a porphyrin pi cation radical in ascorbate peroxidase compound I. Biochemistry 1995; 34: 4331–4341
  • Stuehr D.J., Kwon N.S., Nathan C.F. FAD and GSH participate in macrophage synthesis of nitric oxide. Biochemical and Biophysical Research Communications 1990; 168: 558–565
  • Vasquez-Vivar J., Hogg N., Martasek P., Karoui H., Pritchard K.A., Jr., Kalyanaraman B. Tetrahydrobiopterin-dependent inhibition of superoxide generation from neuronal nitric oxide synthase. Journal of Biological Chemistry 1999; 274: 26736–26742
  • Stuehr D.J. Mammalian nitric oxide synthases. Biochimica et Biophysica Acta 1999; 1411217–1411230
  • Hurshmann A.R., Krebs C., Edmondson D.E., Huynh B.H., Marletta M.A. Formation of a pterin radical in the reaction of the heme domain of inducible nitric oxide synthase with oxygen. Biochemistry 1999; 38: 15689–15696
  • Vasquez-Vivar J., Kalyanaraman B., Martasek P., Hogg N., Masters B.S.S., Karoui H., Tordo P., Pritchard K.A., Jr. Superoxide generation by endothelial nitric oxide synthase: the influence of cofactors. Proceedings of the National Academy of Sciences of the United States of America 1998; 95: 9220–9225
  • Xia Y., Tsai A.L., Berka V., Zweier J.L. Superoxide generation from endothelial nitric-oxide synthase. A Ca2+/calmodulin-dependent and tetrahydrobiopterin regulatory process. Journal of Biological Chemistry 1998; 273: 25804–25808
  • Huie R.E., Padmaja S. The reaction of NO with superoxide. Free Radical Research Communications 1993; 18: 195–199
  • Ischiropoulos H., Zhu L., Tsai M., Martin J.C., Smith C.D., Beckman J.S. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Archives of Biochemistry and Biophysics 1992; 431–437
  • Alvarez B., Rubbo H., Kirk M., Barnes S., Freeman B.A., Radi R. Peroxynitrite-dependent tryptophan nitration. Chemical Research in Toxicology 1996; 9: 390–396
  • Yermilov V., Yoshie Y., Rubio J., Ohshima H. Effects of carbon dioxide/bicarbonate on induction of DNA single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine and base-propenal mediated by peroxynitrite. FEBS Letters 1996; 399: 67–70
  • Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. Journal of Biological Chemistry 1991; 266: 4244–4250
  • O'Donnell V.B., Eiserich J.P., Chumley P.H., Jablonsky M.J., Rama Krishna N., Kirk M., Barnes S., Darley-Usmar V.M., Freeman B.A. Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion. Chemical Research in Toxicology 1999; 12: 83–92
  • Bartlett D., Church D.F., Bounds P.L., Koppenol W.H. The kinetics of the oxidation of l-ascorbic acid by peroxynitrite. Free Radical in Biology and Medicine 1995; 18: 85–92
  • Hoglen N.C., Waller S.C., Sipes I.G., Liebler D.C. Reactions of peroxynitrite with gamma-tocopherol. Chemical Research in Toxicology 1997; 10: 401–407
  • Ramezanian M.S., Padmaja S., Koppenol W.H. Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chemical Research Toxicology 1996; 9: 232–240
  • Rusche K.M., Marletta M.A. Reconstitution of pterin-free inducible nitric-oxide synthase. Journal of Biological Chemistry 2001; 276: 421–427
  • Milstien S., Katusic Z. Oxidation of tetrahydrobiopterin by peroxynitrite: implications for vascular endothelial function. Biochemical and Biophysical Research Communications 1999; 263: 681–684
  • Kirsch M., Lomonosova E.E., Korth H.G., Sustmann R., de Groot H. Hydrogen peroxide formation by reaction of peroxynitrite with HEPES and related tertiary amines. Implications for a general mechanism. Journal of Biological Chemistry 1998; 273: 12716–12724
  • Mouithys-Mickalad A., Hans P., Deby-Dupont G., Hoebeke M., Deby C., Lamy M. Propofol reacts with peroxynitrite to form a phenoxyl radical: demonstration by electron spin resonance. Biochemical and Biophysical Research Communications 1998; 249: 833–837
  • Mouithys-Mickalad A., Kohnen S., Deby C., Noels A.F., Lamy M., Deby-Dupont G. Peroxynitrite reacts with biological nitrogen-containing cyclic molecules by a radical pathway, as demonstrated by ultraweak luminescence coupled with ESR technique. Biochemical and Biophysical Research Communications 1999; 259: 460–464
  • Uppu R.M., Squadrito G.L., Cueto R., Pryor W.A. Synthesis of peroxynitrite by azide-ozone reaction. Methods in Enzymology 1996; 269: 311–321
  • Koppenol W.H., Kissner R., Beckman J.S. Synthesis of peroxynitrite: to go with the flow or on solid grounds?. Methods in Enzymology 1996; 269: 296–302
  • Bohle D.S., Glassbrenner P.A., Hansert B. Synthesis of pure tetramethylammonium peroxynitrite. Methods in Enzymology 1996; 269: 302–311
  • Bohle D.S., Hansert B., Paulson S.C., Smith B.D. Biomimetic synthesis of the putative cytotoxin peroxynitrite, ONOO-, and its characterization as a tetramethylammonium salt. Journal of the American Chemical Society 1994; 116: 7423–7424
  • Fisher D.B., Kaufman S. Tetrahydropterin oxidation without hydroxylation catalyzed by rat liver phenylalanine hydroxylase. Journal of Biological Chemistry 1973; 248: 4300–4304
  • Giulivi C., Cadenas E. The reaction of ascorbic acid with different heme iron redox states of myoglobin. Antioxidant and prooxidant aspects. FEBS Letters 1993; 332: 287–290
  • Matsui T., Ozaki Si I., Liong E., Philips G.N., Jr, Watanabe Y. Effects of the location of distal histidine in the reaction of myoglobin with hydrogen peroxide. Journal of Biological Chemistry 1999; 274: 2838–2844
  • Tumer J.J.O., Rice-Evans C.A., Davies M.J., Newman E.S.R. The formation of free radicals by cardiac myocytes under oxidative stress and the effects of electron-donating drugs. Biochemical Journal 1991; 277: 833–837
  • Blair J.A., Pearson A.J. Kinetics and mechanism of the autoxidation of the 2-amino-4-hydroxy-5,6,7,8-tetrahydrobiopterines. Journal of Chemical Society, Perkin Transactions 1974; II: 80–88
  • Merenyi G., Lind J., Goldstein S., Czapski G. Peroxynitrous acid homolyzes into ·OH and ·NO2 radicals. Chemical Research in Toxicology 1998; 11: 712–713
  • Kondo T., Riesz P. Hydrogen atom formation by ultrasound in D2O solutions of nitrone spin traps. Free Radical Research Communications 1989; 7: 11–18
  • Kelman D.J., DeGray J., Mason R.P. Reaction of myoglobin with hydrogen peroxide forms a peroxyl radical which oxidizes substrates. Journal of Biological Chemistry 1994; 269: 7458–7463

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