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Original Article

Reactions of Low Valent Transition-Metal Complexes with Hydrogen Peroxide. Are they “Fenton-Like” or Not? 3. The Case of Fe(II){N(CH2CO2)3}(H2O)2

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Pages 231-241 | Published online: 07 Jul 2009

References

  • Fenton H.J.H. Journal of the Chemical Society 1894; 65: 899
  • Haber H., Weiss J. The catalytic decomposition of hydrogen peroxide by iron salts. Proceedings of the Ro-val Society of London Series A. 1934; 147: 332–351
  • Czapski G., Samuni A., Meisel D. The reactions of organic radicals formed by some “Fenton-like” reagents. Journal of Physiology Chemistry 1971; 75: 3271–3280
  • Shiga T. An electron paramagnetic resonance study of alcohol oxidation by Fenton's reagent. Journal of Physics and Chemistry 1965; 69: 3805–3814
  • Bray W.C., Gorin M. Ferryl iron, a compound of tetravalent iron. Journal of the American Chemical Society 1932; 54: 2124–2125
  • Walling C. Fenton's reagent revisited. Account of Chemical Research 1975; 8: 125–131
  • Walling C. The nature of the primary oxidants in oxidations mediated by metal ions. Oxydases and related redox systems, T.E. Kings, H.S. Mason, M. Morison, 1975; 85–97
  • Sheldon R.A., Kochi J.K. Metal catalyzed oxidations of organic compounds. Academic press, NY 1981; 35, 171, 177 and 330
  • Halliwell B., Gutteridge J.M.C. Free radicals in biology and medicine. Claredon Press, Oxford 1985
  • Free radicals, cell damage and disease, C. Rice-Evans. Richelieu Press, London 1986
  • Rice-Evans C., Halliwell B. Free radicals: Methodology and concepts. Richelieu Press, London 1988
  • Rice-Evans C., Dormandy T. Free Radicals: Chemistry. pathology and medicine. Richelieu Press, London 1988
  • Oxygen radicals and tissue injury, B. Halliwell. Upjohn Co. Bethesda, Maryland 1988
  • Cross C.E. Oxygen radicals and human diseases. Annals at Internal Medicine 1987; 107: 526–545
  • Czapski G. On the use of ·OH scavengers in biological systems. Israel Journal of chemistry 1984; 24: 29–32
  • Lynch R.C., Fridovich I. Autoactivation of xanthine oxidase. Biochemical Biophysics Acta 1979; 571: 195–200
  • Chevion M. A site-specific mechanism for free radical induced biological damage: The essential role of redox-active transition metals. Free Radical Biology Medicare 1988; 5: 27–37
  • Johnson G.R.A., Nazhat N.B., Saadalla-Nazhat R.A. Reaction of aquocopper(I) ion with hydrogen peroxide. Evidence against hydroxyl free radical formation. Journal of the Cheniical Society Chemistry Communications 1985; 407–408
  • Johnson G.R.A., Nazhat N.B., Saadalla-Nazhat R.A. Reaction of aquocopper(I) ion with hydrogen peroxide. Journal of the Chemical Society Faraday Transactions 1985; 1, 84: 501–510
  • Masarwa M., Cohen H., Meyerstein D., Hickman D.L., Bakac A., Espenson J.H. Reactions of low valent transition metal complexes with hydrogen-peroxide. Are they “Fenton like” or not? I. The case of Cu+aq and Cr2aq+. Journal of the American Chemical Society 1988; 110: 4293–4297
  • Goldstein S., Czapski G. Mechanism and reaction products of the oxidation of Cu(I) -phenantroline by H2O2. Free Radical Biology Medicare 1985; 1: 373–380
  • Goldstein S., Czapski G. Kinetics of oxidation of cuprous complexes of substituted phenantrolines and 2,2′-bipyridyl by molecular oxygen and by hydrogen peroxide in aqueous solu tion. Inorganic Chemistry 1985; 24: 1087–1092
  • Johnson G.R.A., Nazhat N.B. Kinetics and mechanism of the reaction of the bis(1,10-phenantroline) copper(I) ion with hydrogen peroxide in aqueous solution. Journal of the American Chemical Society 1987; 109: 1990–1994
  • Gorbunova N.V., Purmal A., Skurlatov I.Yu. Reaction of a dipyridyl complex of cop per(+) ion with hydrogen peroxide. Zh. Fiz. Khim. 1975; 49: 1995–1999
  • Koppenol W.H. The reaction of ferrous EDTA with hydrogen peroxide: Evidence against hydroxyl radical formation. Free Radical Biology Medicare 1985; 1: 281–285
  • Rush J.D., Koppenol W.H. Oxidizing intermediates in the reaction of ferrous EDTA with hydrogen peroxide: Reactions with organic molecules and cytochrome c. Journal of Biological Chemistry 1986; 261: 6730–6733
  • Rush J.D., Koppenol W.H. Reactive intermediates formed by the interaction of hydrogen peroxide and ferrous complexes. Free Radicals, Metal Ions and Biopolymers, P.C. Beaumont, D.J. Deeble, B.J. Parsons, C. Rice-evans. Richelieu Press, London 1989; 33–44
  • Rush J.D., Koppenol W.H. Reactions of Fe(II)nta and Fe(II)edda with hydrogen peroxide. Journal of the American Chemical Society 1988; 110: 4957–4963
  • Elliot J.H., Padamski S., Pika J. Free radical redox reactions of uranium ions in sulphuric acid solutions. Canadian Journal of Chemistry 1986; 64: 314–320
  • Khan M.M.T., Husain A., Ramachandraiah G., Moiz M.A. Equilibrium and electrochemi cal studies on the complex formed by the interaction of K[Ru(EDTA-H)Cl]-2H2O with oxygen and hydrogen peroxide. Inorganic Chemistry 1986; 25: 3023–3030
  • Sutton H.C., Winterbourn C.C. On the participation of higher oxidation states of iron and copper in Fenton reactions. Free Radical Biology Medicare 1989; 6: 53–60
  • Vile G.F., Winterbourn C.C., Sutton H.C. Radical-driven Fenton reactions: Studies with Paraquat, Adriamicin, and anthraquinone-6-sulfonate and citrate, ATP, ADP, and pyrophosphate iron chelates. Archives of Biochemistry and Biophysics 1987; 259: 616–626
  • Sutton H.C., Vile G.F., Winterbourn C.C. Radical-driven Fenton reactions: Studies for production of tetravalent iron in the presence and absence of ethylenediaminetetraacetic acid. Archi cal Biochemistry and Biophysics 1987; 256: 462–471
  • Gutteridge J.M.C., Alliwell B.H. The deoxyribose assay: An assay both for “free” hydroxyl radical and for site-specific hydroxyl radical production. Biochemical Journal 1988; 253: 932–933
  • Rahhal S., Richter H.W. Reduction of hydrogen peroxide by the ferrous iron chelate of diethylenetriamine-N,N,N',N',N'-pentaacetate. Journal of the American Chemical Society 1987; 110: 3126–3133
  • Gutteridge J.M.C. Ferrous-salt-promoted damage to deoxyribose and benzoate. The increased effectiveness of hydroxyl-radical scavengers in the presence of EDTA. Biochemical Journal 1987; 243: 709–714
  • Pilas B., Sarna T., Kalyanaraman B., Swartz H.M. The effect of melanin on iron associated decomposition of hydrogen peroxide. Free Radical Biological Medicare 1988; 4: 285–293
  • Winterbourn C.C. The ability of scavengers to distinguish -OH production in the iron catalyzed Haber-Weiss reaction: Comparison of four assays for ·OH. Free Radical Biological Medi care 1987; 3: 33–39
  • Cohen H., Meyerstein D. Equilibrium constants for the homolysis of the metal-carbon σ bond in [(nta}(H2O)M(III)-CH3]-, M = Mn, Fe and Co, in aqueous solutions. Inorganic Chemistry 1988; 27: 3431
  • Yamada M., Okigaki T., Awai M. Enhancing effects of bovine serum albumin on cell injury in vitro induced with Fe-nta. Cell Biology Internal Reports. 1987; 11: 707–715
  • Yamada M., Okigaki T., Awai M. Role of superoxide radicals in cytoxic effects of Fe-NTA in cultured normal liver epithelial cells. Cell Structure and Function 1987; 12: 407–420
  • Goddard I.G., Basford D., Sweeney G. Lipid peroxidation stimulated by iron nitrilo triacetate in rat liver. Biochemistry and Pharmacology 1986; 35: 2381–2387
  • Hamazaki S., Okada S., Toyokuni Jia-Lili S., Midorikawa O. Oxygen reduction and lipid peroxidation by iron chelates with special reference to ferric nitrilotriacetate. Archivery Biochemistry and Biophysics 1989; 272: 10–17
  • Hamazaki S., Okada S., Ebina Y., Jia-Lili, Toyokuni S., Midorikawa O. Effect of dietary vitamin E on ferric nitrilotriacetate-induced nephrotoxicity in rats. Toxercology and Appiral Pharma cology 1989; 92: 500–506
  • Inoue S., Kawanishi S. Hydroxyl radical production and human DNA damage induced by ferric nitrilotriacetate and hydrogen peroxide. Cancer Research 1987; 47: 6522–6527
  • Tulius T.D., Dombroski B.A. Iron(II) EDTA used to measure the helical twist along any DNA molecule. Science 1985; 230: 679–681
  • Tulius T.D., Dombroski B.A. Hydroxyl radical “footprinting”: High resolution informa tion about DNA-protein contacts and application to? represser and Cro protein. Proceedings of the National Academy and Science U.S.A. 1986; 83: 5469–5473
  • Posvic T.J., Dervan P.B. Triple helix formation oligonucleotides on DNA extended to the physiological pH range. Journal at the American Chemical Society 1989; 111: 3059–3061
  • Tachon P. Ferric and cupric ions requirement for DNA single-strand breakage by H2O2. Free Radical Research Communications 1989; 7: 1–10
  • Matyska B., Duskova D. Polarographic reduction of iron(III) ions in the of ethylenediami-netetraacetic acid and hydrogen peroxide. II. Bimolecular reactions in aqueous solution. Chem. Listy 1957; 22: 848–853
  • Borgaard O.K., Farver O., Anderson V.S. Polarographic study of the rate of oxidation of iron(II) chelates by hydrogen peroxide. Acta Chemica Scand 1971; 25: 3541–3543
  • Matheson M.S., Dorfman L. Pulse radiolysis. M.I.T. Press, Cambridge, MA 1969
  • Buxton G.V., Greenstock C.L., Helman W.P., Ross A.B. Critical review of rate constants for reactions of hydrated electrons hydrogen atoms and hydroxyl radicals (.OH/.O-) in aqueous solutions. Journal of Physics and Chemistry Reference Data 1988; 17: 513–886
  • Meyerstein D. Complexes of cations in unstable oxidation states in aqueous solutions as studied by pulse radiolysis. Accounts Chemical Research 1978; 11: 37–43
  • Czapsky G., Goldstein S., Cohen H., Meyerstein D. Formation and decomposition of iron-carbon σ Bonds in the reaction of iron(II)-polyamino-carboxylates with CO2-- free radicals in aqueous solutions. A pulse radiolysis study. Journal at the American Chemical Society 1988; 110: 3903–3907
  • Cohen H., Meyerstein D. Chromium-carbon bonds in aqueous solutions. A pulse radiolytic study. Inorganic Chemistry 1974; 13: 2434–2443
  • Cohen H., Meyerstein D., Shusterman A., Weiss M. A mechanistic study of the beta-Hydroxyl elimination from (H2O)5Cr-CH2C(CH3)2OH2+ in aqueous solutions. Journal at the Ameri can Chemical Society 1984; 106: 1876–1877
  • Freiberg M., Mulac W.A., Schmidt K.H., Meyerstein D. Reactions of aliphatic free radicals with copper cations in aqueous solutions. Part III. Reactions with cuprous ions. A pulse radiolytic study. Journal of the Chemical Society Faraday Society, 1 1980; 76: 1838–1848
  • Cohen H., Meyerstein D. Kinetics of β-hydroxyl elimination from [(H2O)mCuII-CH2C(CH3)2OH]+ in aqueous solutions. A pulse radiolysis study. Journal at the Chemical Society Faraday Transactions 1 1988; 84: 4157–4160
  • Elroi H., Meyerstein D. Kinetics of formation and decomposition of carbon-cobalt(III) bonds in aqueous solutions by the reaction of free radicals with a coenzyme B12r model cobalt(II) Complex. Journal of the American Chemical Society 1978; 100: 5540–5548
  • Sorek Y., Cohen H., Mulac W., Scmidt K.H., Meyerstein D. The reactions of CH2C(CH3)2OH with cobalt(II) tetra-sulpho-phtalocyanine in aqueous solutions. A pulse radiolytic study. Inorganic Chemistry 1983; 22: 3040–3046
  • Sorek Y., Cohen H., Meyerstein D. Mechanistic study of β-hydroxy elimination from [tetra sulfophthalcoyanine Co(III)-CR1 R2CR3R4OH] in aqueous solutions. A pulse radiolysis study. Jour nal of the Chemical Society, Faraday Transactions, 1 1989; 85: 1169–1179
  • Sorek Y., Cohen H., Meyerstein D. Kinetics of the beta-Hydroxyl elimination reactions from (protoporphyrin)iron(III)-CHRCH2OH complexes in aqueous solutions. A pulse-radiolytic study. Journal of the Chemical Society, Faraday Transactions, 1 1986; 82: 3431–3438
  • Goldstein S., Czapski G., Cohen H., Meyerstein D. Formation and decomposition of transient complexes with a copper-carbon σ bond in the reaction of Cu(I)-phenantroline with aliphatic free radicals in aqueous solutions. A pulse radiolysis study. Inorganic Chemistry 1988; 27: 4130–4135
  • Ross A.B., Neta P. Rate constants for reactions of aliphatic free carbon-centered radicals in aqueous solutions. National Standards Reference Data System (U.S. National Bureau of Stan dards.). 1982, NSRDS-70
  • Cohen H., Meyerstein D. Unpublished results
  • Martell A.E., Smith R.M. Critical stability constants, vol 1: Amino acids. Plenum Press, NY 1974; 139–143

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