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Original Article

Reaction of Hydroxyl Radicals with Alkyl Phosphates and the Oxidation of Phosphatoalkyl Radicals by Nitro Compounds

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Pages 121-131 | Received 24 Jan 1995, Accepted 10 Apr 1995, Published online: 03 Jul 2009

References

  • Adams G.E. Hypoxic cell sensitizers for radiotherapy. Radiotherapy, Surgery, and Immunotherapy, F.F. Becker. Plenum, New York 1977; 181–223, In
  • Asmus K.-D., Henglein A., Ebert M., Keene J.P. Pulsradiolytische Untersuchung schneller Reaktionen von hydratisierten Elektronen, freien Radikalen und Ionen mit Tetranitromethan in wäßriger Lösung. Berichte Bunsengesellschaft für Physikalische Chemie 1964; 68: 657–663
  • Asmus K.-D., Möckel H., Henglein A. Pulse radiolytic study of the site of OH radical attack on aliphatic alcohols in aqueous solution. Journal of Physical Chemistry 1973; 77: 1218–1221
  • Bansal K.M., Grätzel M., Henglein A., Janata E. Polarographic and optical absorption studies of radicals produced in the pulse radiolysis of aqueous solutions of ethylene glycol. Journal of Physical Chemistry 1973; 77: 16–19
  • Behrens G., Koltzenburg G., Ritter A., Schulte-Frohlinde D. The influence of protonation or alkylation of the phosphate group on the e.s.r. spectra and on the rate of phosphate elimination from 2-methoxyethyl phosphate 2-yl radicals. International Journal of Radiation Biology 1978; 33: 163–171
  • 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 solution. Journal of Physical and Chemical Reference Data 1988; 17: 513–886
  • Chapman J.D., Greenstock C.L., Reuvers A.P., McDonald E., Dunlop I. Radiation chemical studies with nitrofurazone as related to its mechanism of radiosensitization. Radiation Research 1973; 53: 190–203
  • Dizdaroglu M., Henneberg D., von Sonntag C. The mass spectra of TMS-ethers of deuterated polyalcohols. A contribution to the structural investigation of sugars. Organic Mass Spectrometry 1974; 8: 335–345
  • Dizdaroglu M., Henneberg D., von Sonntag C., Schuchmann M.N. Mass spectra of trimethylsilyl di-O-methyloximes of adosuloses and dialdoses. Organic Mass Spectrometry 1977; 12: 772–776
  • Dutton G.R., Noller C.R. Syntheses of alkyl phosphates. Organic Syntheses 1948; 2: 109–110
  • Eibenberger J., Schulte-Frohlinde D., Steenkens S. One-electron oxidation of α-monoalkoxyalkyl radicals by tetranitromethane via an intermediate adduct. Influence of radical structure on rate of decomposition of the adduct. Journal of Physical Chemistry 1980; 84: 704–710
  • Fiszer B., Michalski J. Uproszczony sposob otrzymywania chlorofosfonianow dwualkilowych. Roczniki Chemii 1952; 26: 688–689
  • Fitchett M., Gilbert B.S., Willson R.L. Fragmentation reactions of radicals formed from sugar phosphates and the hydroxyl radical: an investigation by electron spin resonance spectroscopy and pulse radiolysis. Journal of the Chemical Society, Perkin Transactions 2 1988; 673–689
  • Fujita S., Steenken S. Pattern of OH radical addition to uracil and methyl- and carboxyl-substituted uracils. Electron transfer of OH adducts with N,N,N′,N′-tetramethyl-p-phenylenediamine and tetranitromethane. Journal of the American Chemical Society 1981; 103: 2540–2545
  • Göbl M., Asmus K.-D. The reaction of α-(alkylthio)alkyl radicals with tetranitromethane. Pulse radiolysis evidence for an intermediate radical adduct. Journal of the Chemical Society, Perkin Transactions 2 1984; 691–697
  • Greenstock C.L., Raleigh J., McDonald E., Whitehouse R. Nucleotide radical oxidation and additional reactions with cellular radiosensitizers. Biochemical and Biophysical Research Communications 1973; 52: 276–283
  • Greenstock C.L., Shierman E. Radiosensitivity and hydroxyl radical reactivity of phosphate esters as measured by radiation-induced dephosphorylation. International Journal of Radiation Biology 1975; 28: 1–12
  • Halmann M., Platzner I. The photochemistry of phosphorus compounds. Part III. Photolysis of ethyl dihydrogen phosphate in aqueous solution. Journal of the Chemical Society 1965; 5380–5385
  • Hissung A., von Sonntag C. The reaction of solvated electrons with cytosine, 5-methylcytosine and 2′-deoxycytidine in aqueous solution. The reaction of the electron adduct intermediates with water, p-nitroacetophenone and oxygen. A pulse spectroscopic and pulse conductometric study. International Journal of Radiation Biology 1979; 35: 449–458
  • Hissung A., von Sonntag C., Veltwisch D., Asmus K.-D. The reaction of the 2′-deoxyadenosine electron adduct in aqueous solution. The effects of the radiosensitizer p-nitroacetophenone. A pulse spectroscopic and pulse conductometric study. International Journal of Radiation Biology 1981; 39: 63–71
  • Jagannadham V., Steenken S. One-electron reduction of nitrobenzenes by α-hydroxyalkyl radicals via addition/elimination. An example of an organic inner-sphere electron-transfer reaction. Journal of the American Chemical Society 1984; 106: 6542–6551
  • Jagannadham V., Steenken S. Reactivity of α-heteroatom-substituted alkyl radicals with nitrobenzenes in aqueous solution: an entropy-controlled electron-transfer/addition mechanism. Journal of the American Chemical Society 1988; 110: 2188–2192
  • Kappen L.S., Goldberg I.H. Nitroaromatic radiation sensitizers substitute for oxygen in neocarzinostatin-induced DNA damage. Proceedings of the National Academy of Sciences, USA. 1984; 81: 3312–3316
  • Kappen L.S., Lee T.R., Yang C.-C., Goldberg I.H. Oxygen transfer from the nitro group of a nitroaromatic radiosensitizer to a DNA sugar damage product. Biochemistry 1989; 28: 4540–4542
  • McIvor R.A., McCarthy G.D., Grant G.A. Preparation and toxicity of some alkyl thiopyrophosphates. Canadian Journal of Chemistry 1956; 34: 1819–1832
  • McMillan M., Norman R.O.C. Electron spin resonance studies. Part XVII. Reactions of some radicals with nitroalkanes. Journal of the Chemical Society (B) 1968; 590–597
  • Michaels H.B., Rasburn E.J., Hunt J.W. Interaction of the radiosensitizer paranitroacetophenone with radiation-induced radicals on nucleic acid components. Radiation Research 1976; 65: 250–267
  • Montgomery H.A.C., Turnbull J.H. Phosphoramidic halides: phosphorylating agents derived from morpholine. Journal of the Chemical Society 1958; 1963–1967
  • Nese C., Schuchmann M.N., Steenken S., von Sonntag C. Oxidation vs. fragmentation in radiosensitization. The reactions of α-alkoxyalkyl radicals with 4-nitrobenzonitrile and oxygen. A pulse radiolysis and product analysis study. Journal of the Chemical Society, Perkin Transactions 1995; 2: 1033–1044
  • Neta P., Huie R.E., Ross A.B. Rate constants for reactions of inorganic radicals in aqueous solution. Journal of Physical and Chemical Reference Data 1988; 17: 1027–1284
  • Ottolenghi M., Rabani J. Photochemical generation of nitrogen dioxide in aqueous solutions. Journal of Physical Chemistry 1968; 72: 593–598
  • Raleigh J.A., Greenstock C.L., Kremers W. Chemical radiosensitization of phosphate ester cleavage. International Journal of Radiation Biology 1973; 23: 457–467
  • Raleigh J.A., Whitehouse R., Kremers W. Effect of oxygen and nitroaromatic cell radiosensitizers on radiation-induced phosphate release from 3′- and 5′-nucleotides: a model for nucleic acids. Radiation Research 1974; 59: 453–465
  • Samuni A., Neta P. Hydroxyl radical reaction with phosphate esters and the mechanism of phosphate cleavage. Journal of Physical Chemistry 1973; 77: 2425–2429
  • Scholes G., Taylor W., Weiss J. Chemical action of ionizing radiations in solution. Part XVIII. Action of X-rays (200 kv) on α- and β-glycerophosphate in aqueous solution. Journal of the Chemical Society 1957; 235–246
  • Schuchmann M.N., von Sonntag C. Radiolysis of di- and trimethylphosphates in oxygenated aqueous solution: a model system for DNA strand breakage. Journal of the Chemical Society, Perkin Transactions 2 1984; 699–704
  • Schuchmann M.N., Zegota H., von Sonntag C. Reactions of peroxyl radicals derived from alkyl phosphates in aqueous solution—model system for DNA strand breakage. Oxygen Radicals in Chemistry and Biology, W. Bors, M. Saran, D. Tait. Walter de Gruyter, Berlin 1984; 629–635, In
  • Steenken S. Oxidation of phenolates and phenylenediamines by 2-alkanonyl radicals produced from 1,2-dihydroxy- and 1-hydroxy-2-alkoxyalkyl radicals. Journal of Physical Chemistry 1979; 83: 595–599
  • Steenken S., Behrens G., Schulte-Frohlinde D. Radiation chemistry of DNA model compounds. Part IV. Phosphate ester cleavage in radicals derived from glycerol phosphates. International Journal of Radiation Biology 1974; 25: 205–210
  • von Sonntag C. The Chemical Basis of Radiation Biology. Taylor & Francis, London 1987; 295–324
  • von Sonntag C., Ansorge G., Sugimori A., Omori T., Koltzenburg G., Schulte-Frohlinde D. Radiation chemistry of DNA model compounds. Part II. Alkyl phosphate cleavage of aliphatic phosphates induced by hydrated electrons and by OH radicals. Zeitschrift für Naturforschung 1972; 27b: 471–472
  • von Sonntag C., Schuchmann H.P. The elucidation of peroxyl radical reactions in aqueous solution with the help of radiation-chemical methods. Angewandte Chemie, International Edition English 1991; 30: 1229–1249
  • von Sonntag C., Schuchmann H.P. Pulse radiolysis. Methods in Enzymology, vol. 233, Oxygen Radicals in Biological Systems, Part C, L. Packer. Academic, Orlando 1994; 3–20, In
  • Wardman P. The use of nitroaromatic compounds as hypoxic cell radiosensitizers. Current Topics in Radiation Research Quarterly 1977; 11: 347–398
  • Wardman P. The mechanism of radiosensitization by electron-affinic compounds. Radiation Physics and Chemistry 1987; 30: 423–432
  • Wardman P., Clarke E.D. Electron transfer and radical-addition in the radiosensitization and chemotherapy of hypoxic cells. New Chemo- and Radiosensitizing Drugs, A. Breccia, J.F. Fowler. Edizione Scientifiche, Lo Scarabeo 1985; 21–38, In
  • Whillans D.W. The reactions of p-nitroacetophenone with H and OH radicals. Radiation Physics and Chemistry 1977; 10: 335–340

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