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Xenobiotica
the fate of foreign compounds in biological systems
Volume 25, 1995 - Issue 7
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Original Article

Haemoprotein-mediated metabolism of enamines and the possible involvement of one-electron oxidations

L. M. Sayre Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA
,
D. A. Engelhart Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA
,
D. V. Nadkarni Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA
,
M. K. M. Babu Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA
,
M. E. Klein Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA
&
G. McCoy Department of Environmental Health Sciences, Case Western Reserve University, Cleveland, OH, 44106, USA
Pages 769-775 | Received 10 Dec 1994, Published online: 27 Aug 2009

References

  • Garst M. E., Bonfiglio J. N., Grudoski D. A., Marks J. Specific enolates from α-amino ketones. Journal of Organic Chemistry 1980; 45: 2307–2315
  • Hoag M. K. P., Schmidt-Peetz M., Lampen P., Trevor A., Castagnoli N., Jr. Metabolic studies on phencyclidine: Characterization of a phencyclidine iminium ion metabolite. Chemical Research in Toxicology 1988; 1: 128–131
  • Hoag M. K. P., Trevor A. J., Asscher Y., Weissman J., Castagnoli N., Jr. Metabolism-dependent inactivation of liver microsomal enzymes by phencyclidine. Drug Metabolism and Disposition 1984; 12: 371–375
  • Hoag M. K. P., Trevor A. J., Kalir A., Castagnoli N., Jr. Phencyclidine iminium ion. NADPH-dependent metabolism, covalent binding to macromolecules, and inactivation of cytochrome(s) P450. Drug Metabolism and Disposition 1987; 15: 485–490
  • Huang J., Dunford H. B. Oxidation of substituted anilines by horseradish peroxidase compound II. Canadian Journal of Chemistry 1990; 68: 2159–2163
  • Huang J., Dunford H. B. One-electron oxidative activation of 2-aminofluorene by horseradish peroxidase compounds I and II: spectral and kinetic studies. Archives in Biochemistry and Biophysics 1991; 287: 257–262
  • Kersten P. J., Kalyanaraman B., Hammel K. E., Reinhammar B., Kirk T. K. Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes. Biochemical Journal 1990; 268: 475–480
  • Leonard N. J., Hauck F. P., Jr. Unsaturated amines. X. The mercuric acetate route to substituted piperidines, Δ2-tetrahydropyridines and Δ2-tetrahydroanabasines. Journal of the American Chemical Society 1957; 79: 5279–5292
  • Masumoto H., Ohta A., Hirobe M. Application of chemical cytochrome P450 model systems to studies on drug metabolism. IV. Mechanism of piperidine metabolism pathways via an iminium intermediate. Drug Metabolism and Disposition 1991; 19: 768–780
  • Masumoto H., Takeuchi K., Ohta S., Hirobe M. Application of chemical P450 model systems to studies on drug metabolism. I. Phencyclidine: a multi-functional model substrate. Chemical and Pharmaceutical Bulletin 1989; 37: 1788–1794
  • Nguyen T.-L., Gruenke L. D., Castagnoli N., Jr. Metabolic oxidation of nicotine to chemically reactive intermediates. Journal of Medical Chemistry 1979; 22: 259–263
  • Ortiz de Montellano P. R., David S. K., Ator M. A., Tew D. Mechanism-based inactivation of horseradish peroxidase by sodium azide. Formation of meso-azidoporphyrin IX. Biochemistry 1988; 27: 5470–5476
  • Osawa Y., Coon M. J. Selective mechanism-based inactivation of the major phenobarbital-inducible P450 cytochrome from rabbit liver by phencyclidine and its oxidation product, the iminium compound. Drug Metabolism and Disposition 1989; 17: 7–13
  • Overton M., Hickman J. A., Threadgill M. D., Vaughan K., Gescher A. The generation of potentially toxic, reactive iminium ions from the oxidative metabolism of xenobiotic N-alkyl compounds. Biochemical Pharmacology 1985; 34: 2055–2061
  • Sayre L. M., Engelhart D. A., Venkataraman B., Babu M. K. M., McCoy G. D. Generation and fate of enamines in the microsomal metabolism of cyclic tertiary amines. Biochemical and Biophysical Research Communications 1991; 179: 1368–1376
  • Shigenaga M. K., Trevor A. J., Castagnoli N., Jr. Metabolism-dependent covalent binding of (S)-[5-3H]nicotine to liver and lung microsomal macromolecules. Drug Metabolism and Disposition 1988; 16: 397–402
  • Szutowicz A., Kobes R. D., Orsulak P. J. Colorimetric assay for monoamine oxidase in tissues using peroxidase and 2,2′-azinodi(3-ethylbenzthiazoline-6-sulfonic acid) as chromogen. Analytical Biochemistry 1984; 138: 86–94
  • Van der Zee J., Duling D. E., Mason R. P., Eling T. E. The oxidation of N-substituted aromatic amines by horseradish peroxidase. Journal of Biological Chemistry 1989; 264: 19828–19836
  • Ward D. P., Trevor A. J., Kalir A., Adams J. D., Baillie T. A., Castagnoli N., Jr. Metabolism of phencyclidine. The role of iminium ion formation in covalent binding to rabbit microsomal protein. Drug Metabolism and Disposition 1982; 10: 690–695
  • Yates P., MacLachlan F. N. Tetrahydroindolizine-3,8 (2H, 5H)-dione and related 3-piperidones. Journal of the Indian Chemical Society 1978; 55: 1116–1121

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