N-Hydroxy-N-arylacetamides. V. Differences in the Mechanism of Haemoglobin Oxidation in Vitro, by N-hydroxy-4-Chloroacetanilide and N-Hydroxy-4-Chloroaniline

References

• Antonini E., Wyman J., Brunori M., Taylor J. F., Rossi‐Fanelli A., Caputo A. Studies on the oxidation‐reduction potentials of heme proteins. I. Human hemoglobin. Journal of Biological Chemistry 1964; 239: 907–912
   PubMed Web of Science ®Google Scholar
• Bowman D. F., Brokenshire J. L., Gillan T., Ingold K. U. Kinetic applications of electron paramagnetic resonance spectroscopy. II. Self‐reactions of N‐alkyl nitroxides and N‐phenyl nitroxide. Journal of the American Chemical Society 1971; 93: 6551–6561
   Web of Science ®Google Scholar
• Dannenberg H., Kiese M. Kinetik der Hämiglobinbildung. V. Nachweis von Nitrosobenzol in roten Zellen bei der Hämiglobinbildung durch Phenylhydroxylamin. Naunyn‐Schmiedeberg's Archiv für experimentelle Pathologie und Pharmakologie 1950; 211: 102–114
   PubMedGoogle Scholar
• Evelyn K. A., Malloy H. T. Microdetermination of oxyhemoglobin methemoglobin, and sulfhemoglobin in a single sample of blood. Journal of Biological Chemistry 1938; 128: 655–662
   Google Scholar
• Eyer P., Ascherl M. Reactions of para‐substituted nitrosobenzenes with human hemoglobin. Biological Chemistry Hoppe‐Seyler 1987; 368: 285–294
   PubMed Web of Science ®Google Scholar
• Eyer P., Hertle H., Kiese M., Klein G. Kinetics of ferrihemoglobin formation by some reducing agents, and the role of hydrogen peroxide. Molecular Pharmacology 1975; 11: 326–334
   PubMed Web of Science ®Google Scholar
• Eyer P., Lengfelder E. Radical formation during autoxidation of 4‐dimethylaminophenol and some properties of the reaction products. Biochemical Pharmacology 1984; 33: 1005–1013
   PubMed Web of Science ®Google Scholar
• Forrester A. R., Ogilvy M. M., Thompson R. H. Mode of action of carcinogenic amines. Part I. Oxidation of N‐aryl‐hydroxamic acids. Journal of the Chemical Society (London(C) 1970; 1081–1083
   Google Scholar
• Haworth R. D., Lapworth A. Reduction of emulsified nitro compounds. I. β‐Phenylhydroxylamine from nitrobenzene. Journal of the Chemical Society (London) 1921; 119: 765–768
   Google Scholar
• Heilmair R., Lenk W., Sterzl H. N‐Hydroxy‐N‐arylacetamides‐IV Differences in the mechanism of haemoglobin oxidation in vitro between N‐hydroxy‐N‐arylacetamides and arylhydroxylamines. Biochemical Pharmacology 1987; 36: 2963–2972
   PubMed Web of Science ®Google Scholar
• Heubner W., Meier R., Rhode H. 33. Studien über Methämoglobinbildung. V. Mitteilung: Phenylhydroxylamin. Naunyn‐Schmiedeberg's Archiv für experimentelle Pathologie und Pharmakologie 1923; 100: 149–161
   Google Scholar
• Heumann K. über chlorierte Azoderivate des Benzols. Berichte der Deutschen Chemischen Gesellschaft 1972; 5: 910–915
   Google Scholar
• Hildebrandt A. G., Roots I., Tjoe M., Heinemeyer G. Hydrogen peroxide in hepatic microsomes. Methods in Enzymology, S. Fleischer, L. Packer. Academic Press, New York 1978; Vol. LII: 342–350
   Google Scholar
• James B. R. Interaction of dioxygen with metalloporphyrin. The Porphyrins, D. Dolphin. Academic Press, London 1978; Vol. 5: 205–295
   Google Scholar
• Keilin D., Hartree E. F. Reaction of methaemoglobin with hydrogen peroxide. Nature 1950; 166: 513–514
   PubMed Web of Science ®Google Scholar
• Kiese M. Ferrihemoglobinemia, A Comprehensive Treatise. CRC Press, Cleveland, Ohio 1974
   Google Scholar
• Kiese M., Reinwein I. Kinetik der Hämiglobinbildung. IX. Die Reduktion von Hämiglobin durch Phenylhydroxylamin. Naunyn‐Schmiedeberg's Archiv für experimentelle Pathologie und Pharmakologie 1950; 211: 402–409
   PubMedGoogle Scholar
• Kiese M., Renner G. Metabolism of N,N‐dimethylaniline in the dog. Naunyn‐Schmiedeberg's Archiv für experimentelle Pathologie und Pharmakologie 1971; 270: R72
   Google Scholar
• Kiese M., von Ruckteschell A. Kinetik der Hämiglobinbildung. XI. Die katalytische Wirkung des Hämoglobins auf die Oxidation von Phneylhydroxylamin durch Sauerstoff. Naunyn‐Schmiedeberg's Archiv für experimentelle Pathologie und Pharmakologie 1951; 213: 128–138
   PubMedGoogle Scholar
• Kiese M., Taeger K. The fate of phenylhydroxylamine in human red cells. Naunyn‐Schmiedeberg's Archives of Pharmacology 1976; 292: 59–66
   PubMed Web of Science ®Google Scholar
• Lenk W., Sterzl H. N‐Hydroxy‐N‐arylacetamides. III. Mechanism of haemoglobin oxidation by N‐hydroxy‐4‐chloroacetanilide in erythrocytes in vitro. Xenobiotica 1987; 17: 499–512
   PubMed Web of Science ®Google Scholar
• Ogata Y., Sawaki Y., Mibae J., Morimoto T. Kinetics of the autoxidation of phenylhydroxylamines to azoxybenzenes in methanol. Journal of the American Chemical Society 1964; 86: 3854
   Web of Science ®Google Scholar
• Peisach J., Blumenberg W. E., Wittenberg B. A., Wittenberg J. B. The electronic structure of protoheme proteins. III. Configuration of the heme and its ligands. Journal of Biological Chemistry 1968; 243: 1871–1880
   PubMed Web of Science ®Google Scholar
• Riedl M. Das electrochemische Verhalten von N‐Arylacetohydroxamsäuren. Diplomarbeit LM‐Univ, München 1983
   Google Scholar
• Steenken S., Neta P. One‐electron redox potentials of phenols. Hydroxy‐and aminophenols and related compounds of biological interest. The Journal of Physical Chemistry 1982; 86: 3661–3667
   Web of Science ®Google Scholar
• Wallace W. J., Caughey W. S. Mechanism for the autoxidation of hemoglobin by phenols, nitrite and ‘oxidant’ drugs. Peroxide formation by one electron donation to bound dioxygen. Biochemical Biophysical Research Communications 1975; 62: 561–567
   PubMed Web of Science ®Google Scholar
• Weiss J. J. Nature of iron‐oxygen‐bond in oxyhaemoglobin. Nature 1964; 202: 83–84
   PubMed Web of Science ®Google Scholar