Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 24, 1994 - Issue 1
52
Views
19
CrossRef citations to date
0
Altmetric
Original Article

Electron transfer in P450 mechanisms. Microsomal metabolism of cyclopropylbenzene and p-cyclopropylanisole

&
Pages 1-16 | Received 16 Sep 1993, Published online: 27 Aug 2009

References

  • Baciocchi E., Crescenzi M., Lanzalunga O. Hydrogen atom transfer vs. electron transfer in iron (III) porphyrin-catalyzed benzylic oxidation. Journal of the Chemical Society Chemical Communications 1991a; 1990: 687–688
  • Baciocchi E., Mattioli M., Romano R., Ruzzioni R. Anodic oxidation of α-substituted p-xylenes. Electronic and stereo-electronic effects of α-substituents in the deprotection of alkylaromatic radical cations. Journal of Organic Chemistry 1991b; 56: 7154–7160
  • Bowry V. W., Ingold K. U. A radical clock investigation of cytochrome P-450 hydroxylation of hydrocarbons. Rate of oxygen rebound. Journal of the American Chemical Society 1991; 113: 5699–5707
  • Bradford M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry 1976; 76: 248–254
  • Canan Koch S. S., Chamberlain A. R. Modified conditions for efficient Baeyer-Viliger oxidation with m-CPBA. Synthetic Communications 1989; 19: 829–833
  • Cavalieri E., Rogan E. Metabolic activation by one-electron and two-electron oxidation in aromatic hydrocarbon carcinogenesis. Chemical Induction of Cancer, Y.-T. Woo, D.-Y. Lui, J. C. Arcos, M. F. Argus. Academic, New York 1985; 533–564
  • DePuy C. H., Dappen G. M., Eilers K. L., Klein R. A. The chemistry of cyclopropanols. II. Synthetic methods. Journal of Organic Chemistry 1964; 29: 2813–2818
  • Eberson L. Studies on electrolytic substitution reactions. III. Isomer distributions and isotope effects in nuclear and side-chain anodic acetoxylation of aromatic compounds. Journal of the American Chemical Society 1967; 89: 4669–4676
  • Eberson L. Electron-transfer reactions in organic chemistry. 4. A mechanistic study of the oxidation of p-methoxytoluene by 12-tungstocobalt(III)ate ion. Journal of the American Chemical Society 1983; 105: 3192–3199
  • Fu H., Newcomb M., Wong C.-H. Pseudomonas oleovorans monooxygenase catalyzed asymmetric epoxidation of allyl alcohol derivatives and hydroxylation of a hypersensitive radical probe with the radical ring opening rate exceeding the oxygen rebound rate. Journal of the American Chemical Society 1991; 113: 5878–5880
  • Guengerich F. P. Enzymatic oxidation of xenobiotic chemicals. CRC Critical Reviews of Biochemistry and Molecular Biology 1990; 25: 97–153
  • Guengerich F. P., Willard R. J., Shea J. P., Richards L. E., McDonald T. L. Mechanism-based inactivation of cytochrome P-450 by heteroatom-substituted cyclopropanes and formation of ring-opened products. Journal of the American Chemical Society 1984; 106: 6446–6447
  • Hahn R. C., Corbin T. F., Schechter H. Electrical effects of cycloalkyl groups. Journal of the American Chemical Society 1968; 90: 3404–3414
  • Hanzlik R. P., Hogberg K., Judson C. M. Microsomal hydroxylation of specifically deuterated monosubstituted benzenes. Evidence for direct aromatic hydroxylation. Biochemistry 1984; 23: 3048–3055
  • Hanzlik R. P., Kishore V., Tullman R. Cyclopropylamines as suicide substrates for cytochrome P-450. Journal of Medicinal Chemistry 1979; 22: 760–761
  • Hanzlik R. P., Shearer G. O. Secondary deuterium isotope effects on olefin epoxidation by cytochrome P-450. Biochemical Pharmacology 1978; 27: 1441–1444
  • Hart H., Schlossberg R. H., Murray R. K. The acetylation of phenylcyclopropane. Journal of Organic Chemistry 1968; 33: 3800–3803
  • Korzekwa K. R., Swinney D. C., Trager W. F. Isotopically labelled chlorobenzenes as probes for the mechanism of cytochrome P-450 catalyzed aromatic hydroxylation. Biochemistry 1989; 28: 9019–9027
  • Lau S. S., Zannoni V. G. Hepatic microsomal epoxidation of bromobenzene to phenols and its toxicological implications. Toxicology and Applied Pharmacology 1979; 50: 309–318
  • Lau S. S., Zannoni V. G. Bromobenzene metabolism in the rabbit. Specific forms of cytochrome P-450 involved in 2,3- and 3,4-epoxidation. Molecular Pharmacology 1981; 20: 234–235
  • Lee J. S., Jacobsen N. E., Ortiz DE Montellano P. R. 4-Alkyl radical extrusion in the cytochrome P-450 catalyzed oxidation of 4-alkyl-1,4-dihydropyridines. Biochemistry 1988; 27: 7703–7710
  • Ling K.-H. J., Hanzlik R. P. Deuterium isotope effects on toluene metabolism. Product release as a rate-limiting step in cytochrome P-450 catalysis. Biochemical Biophysical Research Communications 1989; 160: 844–849
  • Miwa G. T., Walsh J. S., Kedderis G. L., Hollenberg P. F. The use of intramolecular isotope effects to distinguish between deprotonation and hydrogen atom abstraction mechanisms in cytochrome P-450- and peroxidase catalyzed N-demethylation reactions. Journal of Biological Chemistry 1983; 258: 14445–14449
  • Nakajima T., Wang R.-S., Wlovaara E., Park S. S., Gelboin H. V., Heitanen E., Vainio H. Monoclonal antibody-directed characterization of cytochrome P450 isoenzymes responsible for toluene metabolism in rat liver. Biochemical Pharmacology 1991; 41: 395–404
  • Narasimhan N., Weller P. E., Buben J. A., Wiley R. A., Hanzlik R. P. Microsomal metabolism and covalent binding of [3H/14C]-bromobenzene. Evidence for quinones as reactive metabolites. Xenobiotica 1988; 18: 491–499
  • Ouellette R. J., Shaw D. L. The cleavage of cyclopropanes by lead tetraacetate. Journal of the American Chemical Society 1964; 90: 1651–1652
  • Riley P., Hanzlik R. P. Free radical chlorination and one-electron oxidation of arylcyclopropanes. Designer probes for cytochrome P-450 hydroxylation mechanisms. Tetrahedron Letters 1989; 30: 3015–3018
  • Schlesener C. J., Kochi J. K. Stoichiometry and kinetics of p-methoxytoluene oxidation by electron transfer. Mechanistic dichotomy between side chain and nuclear substitution. Journal of Organic Chemistry 1984; 49: 3142–3150
  • Searles S., Jr., Neckerson R. G., Witsiepe W. K. Oxetanes. IX. Structural and solvent effects in the reaction of γ-bromoalcohols with base. Journal of Organic Chemistry 1960; 24: 1839–1843
  • Shono T., Matsumura Y. Organic synthesis by electrolysis. VI. Anodic oxidation of arylcyclopropanes. Journal of Organic Chemistry 1970; 35: 4157–4160
  • Slaughter D. E., Zheng J., Harriman S., Hanzlik R. P. Identification of covalent adducts to protein sulfur nucleophiles by alkaline permethylation. Analytical Biochemistry 1993; 208: 288–295
  • Stearns R. A., Ortiz DE Montellano P. R. Cytochrome P-450 catalyzed oxidation of quadricyclane. Evidence for a radical cation intermediate. Journal of the American Chemical Society 1985; 107: 4081–4082
  • Suckling C. J. The cyclopropyl group in studies of enzyme mechanism and inhibition. Angewante Chemie, International Edition in English 1988; 27: 537–552
  • Suckling C. J., Nonhebel D. C., Brown L., Suckling K. E., Seilman S., Wolf C. R. Oxidation of arylcyclopropanes by rabbit liver cytochrome P-450. Biochemical Journal 1985; 232: 199–203
  • Suckling K. E., Smellie C. G., Ibrahim I. E.-S., Nonhebel D. C., Suckling C. J. The oxidation of cyclopropyl benzene by rat liver microsomal cytochrome P-450: an unusual triple oxidation of a substrate. FEBS Letters 1982; 145: 179–181
  • Tomaszewski J. E., Jerina D. E., Daly J. W. Deuterium isotope effects during formation of phenols by hepatic monoxygenases. Evidence for an alternative to the arene oxide pathway. Biochemistry 1975; 14: 2024–2031
  • Tullman R. H., Hanzlik R. P. Inactivation of cytochrome P-450 and monoamine oxidase by cyclopropylamines. Drug Metabolism Reviews 1984; 15: 1163–1182
  • White R. E. The involvement of free radicals in the mechanisms of monooxygenases. Pharmacology and Therapeutics 1991; 49: 21–42

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.