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Xenobiotica
the fate of foreign compounds in biological systems
Volume 18, 1988 - Issue 5
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Original Article

Microsomal metabolism and covalent binding of [3H/14C]-bromobenzene. Evidence for quinones as reactive metabolites

N. Narasimhan Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas, 66045-2500, USA
,
Paul E. Weller Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas, 66045-2500, USA
,
John A. Buben Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas, 66045-2500, USA
,
Robert A. Wiley Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas, 66045-2500, USA
&
Robert P. Hanzlik Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas, 66045-2500, USA
Pages 491-499 | Received 12 May 1987, Accepted 05 Dec 1987, Published online: 30 Sep 2009

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A. M. Hissink, B. Van Ommen & P. J. Van Bladeren. (1996) Dose-dependent kinetics and metabolism of 1,2-dichlorobenzene in rat: effect of pretreatment with phenobarbital. Xenobiotica 26:1, pages 89-105.
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P. N. Rizk & R. P. Hanzlik. (1995) Oxidative and non-oxidative metabolism of 4-iodoanisole by rat liver microsomes. Xenobiotica 25:2, pages 143-150.
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P. Riley & R. P. Hanzlik. (1994) Electron transfer in P450 mechanisms. Microsomal metabolism of cyclopropylbenzene and p-cyclopropylanisole. Xenobiotica 24:1, pages 1-16.
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L. R. Hall & R. P. Hanzlik. (1991) N-Dealkylation of tertiary amides by cytochrome P-450. Xenobiotica 21:9, pages 1127-1138.
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J. Zheng & R. P. Hanzlik. (1991) Premercapturic acid metabolites of bromobenzene derived via its 2,3- and 3,4-oxide metabolites. Xenobiotica 21:4, pages 535-546.
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Nicholas E. Weber. (1990) Overview of Bound Residue Chemistry. Drug Metabolism Reviews 22:6-8, pages 611-615.
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Rune Becher, Jon E. Dahl, Kjell Aarstad, Odd C. Nilsen & Erik Dybing. (1989) Lung and Liver Damage in Mice After Bromobenzene Inhalation: Effects of Enzyme Inducers. Inhalation Toxicology 1:2, pages 181-196.
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John A. Buben, N. Narasimhan & Robert P. Hanzlik. (1988) Effects of chemical and enzymic probes on microsomal covalent binding of bromobenzene and derivatives. Evidence for quinones as reactive metabolites. Xenobiotica 18:5, pages 501-510.
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Matthew A. Cerny & Robert P. Hanzlik. (2006) Cytochrome P450-Catalyzed Oxidation of N -Benzyl- N -cyclopropylamine Generates Both Cyclopropanone Hydrate and 3-Hydroxypropionaldehyde via Hydrogen Abstraction, Not Single Electron Transfer . Journal of the American Chemical Society 128:10, pages 3346-3354.
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Jong Cheol Park, Won Dong Han, Jeong Ro Park, Seong Hee Choi & Jong Won Choi. (2005) Changes in hepatic drug metabolizing enzymes and lipid peroxidation by methanol extract and major compound of Orostachys japonicus. Journal of Ethnopharmacology 102:3, pages 313-318.
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Matthew A. Cerny & Robert P. Hanzlik. (2005) Cyclopropylamine inactivation of cytochromes P450: Role of metabolic intermediate complexes. Archives of Biochemistry and Biophysics 436:2, pages 265-275.
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Joseph W. DePierre. 2003. Organic Bromine and Iodine Compounds. Organic Bromine and Iodine Compounds 205 251 .
Stephane Mabie, Kay Castagnoli & Neal Castagnoli. 1999. Handbook of Drug Metabolism. Handbook of Drug Metabolism 49 79 .
Elizabeth M. Rombach & Robert P. Hanzlik. (1999) Detection of Adducts of Bromobenzene 3,4-Oxide with Rat Liver Microsomal Protein Sulfhydryl Groups Using Specific Antibodies. Chemical Research in Toxicology 12:2, pages 159-163.
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Bo Han Wang, Katherine A. Zuzel, Khalid Rahman & David Billington. (1999) Treatment with aged garlic extract protects against bromobenzene toxicity to precision cut rat liver slices. Toxicology 132:2-3, pages 215-225.
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Bo Han Wang, Katherine A Zuzel, Khalid Rahman & David Billington. (1998) Protective effects of aged garlic extract against bromobenzene toxicity to precision cut rat liver slices. Toxicology 126:3, pages 213-222.
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Hao Chen, Marcel J. de Groot, Nico P. E. Vermeulen & Robert P. Hanzlik. (1997) Oxidative N-Dealkylation of p -Cyclopropyl- N,N -dimethylaniline. A Substituent Effect on a Radical-Clock Reaction Rationalized by Ab Initio Calculations on Radical Cation Intermediates . The Journal of Organic Chemistry 62:23, pages 8227-8230.
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Arendina M. Hissink, Martin J. Oudshoorn, Ben Van Ommen, Guido R. M. M. Haenen & Peter J. Van Bladeren. (1996) Differences in Cytochrome P450-Mediated Biotransformation of 1,2-Dichlorobenzene by Rat and Man:  Implications for Human Risk Assessment. Chemical Research in Toxicology 9:8, pages 1249-1256.
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W.C. Mennes, C.W.M. van Holsteijn, A.A.J. van Iersel, S.H. Yap, J. Noordhoek & B.J. Blaauboer. (2016) Interindividual Variation in Biotransformation and Cytotoxicity of Bromobenzene as Determined in Primary Hepatocyte Cultures Derived from Monkey and Human Liver. Human & Experimental Toxicology 13:6, pages 415-421.
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Robyn Fisher, Klaus Brendel & Robert P. Hanzlik. (1993) Correlation of metabolism, covalent binding and toxicity for a series of bromobenzene derivatives using rat liver slices in vitro. Chemico-Biological Interactions 88:2-3, pages 191-208.
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Ivonne M. C. M. Rietjens, Ans E. M. F. Soffers, Cees Veeger & Jacques Vervoort. (2002) Regioselectivity of cytochrome P-450 catalyzed hydroxylation of fluorobenzenes predicted by calculated frontier orbital substrate characteristics. Biochemistry 32:18, pages 4801-4812.
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Cathaline den Besten, Marlies Ellenbroek, Marjan A.E. van der Ree, Ivonne M.C.M. Rietjens & Peter J. van Bladeren. (1992) The involvement of primary and secondary metabolism in the covalent binding of 1,2- and 1,4-dichlorobenzenes. Chemico-Biological Interactions 84:3, pages 259-275.
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Cherukury Madhu & Curtis D. Klaassen. (1992) Bromobenzene-glutathione excretion into bile reflects toxic activation of bromobenzene in rats. Toxicology Letters 60:2, pages 227-236.
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W.C. Mennes, C.W.M. van Holsteijn, J. Noordhoek & B.J. Blaauboer. (1991) Comparative cytotoxicity of bromobenzene in primary cultures of rat and hamster hepatocytes and its relation to biotransformation. Toxicology in Vitro 5:1, pages 63-70.
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William H. Bulger & David Kupfer. (1990) Studies on the formation of methoxychlor-protein adduct in rat and human liver microsomes. Biochemical Pharmacology 40:5, pages 937-945.
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Jon Einar Dahl, Rune Becher, Kjell Aarstad, Odd G. Nilsen & Erik Dybing. (1990) Species differences in short term toxicity from inhalation exposure to bromobenzene. Archives of Toxicology 64:5, pages 370-376.
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Eva B. Brittebo, Catarina Eriksson & Ingvar Brandt. (1990) Activation and toxicity of bromobenzene in nasal tissues in mice. Archives of Toxicology 64:1, pages 54-60.
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Kah-Hiing John Ling & Robert P. Hanzlik. (1989) Deuterium isotope effects on toluene metabolism. Product release as a rate-limiting step in cytochrome P-450 catalysis. Biochemical and Biophysical Research Communications 160:2, pages 844-849.
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