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Xenobiotica
the fate of foreign compounds in biological systems
Volume 20, 1990 - Issue 4
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Research Article

Activation and detoxication of aminophenols. II. Synthesis and structural elucidation of various thiol addition products of 1,4-benzoquinoneimine and N-acetyl-1,4-benzoquinoneimine

K. G. Eckert Walther-Straub-Institut für Pharmakologie und Toxikologie, Ludwig-Maximilians-Universität München, Nuβbaumstraβe 26, D-8000, München, 2, FRG
,
P. Eyer Walther-Straub-Institut für Pharmakologie und Toxikologie, Ludwig-Maximilians-Universität München, Nuβbaumstraβe 26, D-8000, München, 2, FRG
,
J. Sonnenbichler Max-Planck-Institut für Biochemie, Martinsried bei München, Am Klopferspitz, D-8033, Martinsried, FRG
&
I. Zetl Max-Planck-Institut für Biochemie, Martinsried bei München, Am Klopferspitz, D-8033, Martinsried, FRG
Pages 333-350 | Received 15 May 1989, Accepted 15 Nov 1989, Published online: 22 Sep 2008

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Lasantha R. Bandara, Mike D. Kelly, Edward A. Lock & Sandy Kennedy. (2003) A potential biomarker of kidney damage identified by proteomics: preliminary findings. Biomarkers 8:3-4, pages 272-286.
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Wolfgang Dekant & Spiros Vamvakas. (1996) Biotransformation and Membrane Transport in Nephrotoxicity. Critical Reviews in Toxicology 26:3, pages 309-334.
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Serrine S. Lau. (1995) Quinone-Thioether-Mediated Nephrotoxicity. Drug Metabolism Reviews 27:1-2, pages 125-141.
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Y. Tomigahara, K. Shiba, N. Isobe, H. Kaneko, I. Nakatsuka & H. Yamada. (1994) Identification of two new types of S-linked conjugates of Etoc in rat. Xenobiotica 24:9, pages 839-852.
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H.-G. Koebe, S. Pahernik, P. Eyer & F.-W. Schildberg. (1994) Collagen gel immobilization: A useful cell culture technique for long-term metabolic studies on human hepatocytes. Xenobiotica 24:2, pages 95-107.
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W. Dekant & S. Vamvakas. (1993) Glutathione-dependent bioactivation of xenobiotics. Xenobiotica 23:8, pages 873-887.
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Terrence J. Monks & Serrine S. Lau. (1992) Toxicology of Quinone-Thioethers. Critical Reviews in Toxicology 22:5-6, pages 243-270.
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M. W. Anders, W. Dekant & S. Vamvakas. (1992) Glutathione-dependent toxicity. Xenobiotica 22:9-10, pages 1135-1145.
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J. Higaki, J. Kikuchi, Y. Ikenishi & M. Hirata. (1991) Structure determination of a diuretic-glutathione conjugate by mass and n.m.r. spectrometry. Xenobiotica 21:1, pages 47-51.
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Weiyuan Chang, Shrish Barve & Theresa S. Chen. (2012) p-Aminophenol-induced cytotoxicity in Jurkat T Cells: Protective effect of 2(RS)-n-propylthiazolidine-4(R)-carboxylic acid. Journal of Biochemical and Molecular Toxicology 26:2, pages 71-78.
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A. P. Avdeenko, S. A. Konovalova, O. N. Ludchenko, O. P. Ledeneva & A. V. Vakulenko. (2011) Hydrohalogenation of N-acetyl(aroyl)-1,4-benzoquinone monoimines. Russian Journal of Organic Chemistry 47:2, pages 214-229.
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Suramya Waidyanatha & Stephen M. Rappaport. (2008) Hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone in Swiss Webster mice. Chemico-Biological Interactions 172:2, pages 105-114.
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Stephan T. Stern, Mary K. Bruno, Gayle E. Hennig, Robert A. Horton, Jeanette C. Roberts & Steven D. Cohen. (2005) Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity in CD-1 mice: I. Enhancement of acetaminophen nephrotoxicity by acetaminophen-cysteine. Toxicology and Applied Pharmacology 202:2, pages 151-159.
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Xin Fu, Theresa S. Chen, Mukunda B. Ray, Herbert T. Nagasawa & Walter M. Williams. (2004) p ‐Aminophenol‐induced hepatotoxicity in hamsters: Role of glutathione . Journal of Biochemical and Molecular Toxicology 18:3, pages 154-161.
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Wolfgang Dekant. (2001) Chemical-induced nephrotoxicity mediated by glutathione S-conjugate formation. Toxicology Letters 124:1-3, pages 21-36.
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Carmen Alt & Peter Eyer. (1998) Ring Addition of the α-Amino Group of Glutathione Increases the Reactivity of Benzoquinone Thioethers. Chemical Research in Toxicology 11:10, pages 1223-1233.
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Phillip R. Jefferies, Gary B. Quistad & John E. Casida. (1998) Dialkylquinonimines Validated as in Vivo Metabolites of Alachlor, Acetochlor, and Metolachlor Herbicides in Rats. Chemical Research in Toxicology 11:4, pages 353-359.
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W. Dekant. 1997. Risk and Progression Factors in Carcinogenesis. Risk and Progression Factors in Carcinogenesis 77 87 .
Wolfgang Dekant. 1996. Biological Reactive Intermediates V. Biological Reactive Intermediates V 297 312 .
Terrence J. Monks, Maria I. Rivera, Jos J. W. M. Mertens, Melanie M. C. G. Peters & Serrine S. Lau. 1996. Biological Reactive Intermediates V. Biological Reactive Intermediates V 203 212 .
C. Fischer & U. Klotz. (1994) Radical-derived oxidation products of 5-aminosalicylic acid and N-acetyl-5-aminosalicylic acid. Journal of Chromatography B: Biomedical Sciences and Applications 661:1, pages 57-68.
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E LudwigP Eyer. (1994) Structural requirements for the ferrihemoglobin-forming activity of glutathione S-conjugates of 4-dimethylaminophenol.. Environmental Health Perspectives 102:suppl 6, pages 133-136.
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P Eyer. (1994) Reactions of oxidatively activated arylamines with thiols: reaction mechanisms and biologic implications. An overview.. Environmental Health Perspectives 102:suppl 6, pages 123-132.
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Terrence J. Monks & Serrine S. Lau. 1994. 183 210 .
Lynn M. Fowler, John R. Foster & Edward A. Lock. (1994) Nephrotoxicity of 4-amino-3-S-glutathionylphenol and its modulation by metabolism or transport inhibitors. Archives of Toxicology 68:1, pages 15-23.
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T. J. Monks & S. S. Lau. 1994. Conjugation—Deconjugation Reactions in Drug Metabolism and Toxicity. Conjugation—Deconjugation Reactions in Drug Metabolism and Toxicity 459 509 .
Maria L. Anthony, Christopher R. Beddell, John C. Lindon & Jeremy K. Nicholson. (1993) Studies on the effects ofl(αS,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125) on 4-aminophenol-induced nephrotoxicity in the Fischer 344 rat. Archives of Toxicology 67:10, pages 696-705.
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Lynn M. Fowler, John R. Foster & Edward A. Lock. (1993) Effect of ascorbic acid, acivicin and probenecid on the nephrotoxicity of 4-aminophenol in the Fischer 344 rat. Archives of Toxicology 67:9, pages 613-621.
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Edward A. Lock, Theresa J. Cross & Rick G. Schnellmann. (2016) Studies on the Mechanism of 4-Aminophenol-induced Toxicity to Renal Proximal Tubules. Human & Experimental Toxicology 12:5, pages 383-388.
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Joan Jensen, Claus Cornett, Carl Erik Olsen, Jette Tjørnelund & Steen Honoré Hansen. (1993) Synthesis and structural elucidation of glutathione and N-aceyl-cysteine conjugates of 5-aminosalicylic acid. European Journal of Pharmaceutical Sciences 1:3, pages 143-150.
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Christian Störle & Peter Eyer. (1992) Reactions of the wurster's red radical cation with hemoglobin and glutathione during the cooxidation of N,N-dimethyl-p-phenlenediamine and oxyhemoglobin in human red cells. Chemico-Biological Interactions 83:3, pages 271-291.
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Christa Klos, Michael Koob, Christian Kramer & Wolfgang Dekant. (1992) p-Aminophenol nephrotoxicity: Biosynthesis of toxic glutathione conjugates. Toxicology and Applied Pharmacology 115:1, pages 98-106.
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Lynn M. Fowler, Richard B. Moore, John R. Foster & Edward A. Lock. (2016) Nephrotoxicity of 4-Aminophenol Glutathione Conjugate. Human & Experimental Toxicology 10:6, pages 451-459.
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P. Eyer & M. Sprenger. (1991) Orale Verabreichung einer Aktivkohle-Sorbit-Suspension als Erstmaßnahme zur Verminderung der Giftresorption?Oral administration of a charcoal-sorbitol-suspension as a first-line treatment to counteract poison absorption?. Klinische Wochenschrift 69:19, pages 887-894.
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Michael Koob & Wolfgang Dekant. (1991) Bioactivation of xenobiotics by formation of toxic glutathione conjugates. Chemico-Biological Interactions 77:2, pages 107-136.
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Christian Störle & Peter Eyer. (1991) Reactions of the Wurster's blue radical cation with thiols, and some properties of the reaction products. Chemico-Biological Interactions 78:3, pages 333-346.
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Peter Eyer. (1991) Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone. Chemico-Biological Interactions 80:2, pages 159-176.
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P. Eyer. 1991. N-Oxidation of Drugs. N-Oxidation of Drugs 371 391 .

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