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Xenobiotica
the fate of foreign compounds in biological systems
Volume 28, 1998 - Issue 9
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Research Article

Hydrogen atom abstraction of 3,5-disubstituted analogues of paracetamol by horseradish peroxidase and cytochrome P450

J. G. M. BESSEMS Leiden} Amsterdam Center for Drug Research, Department of Pharmacochemistry, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
,
M. J. de GROOT Leiden} Amsterdam Center for Drug Research, Department of Pharmacochemistry, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
,
E. J. BAEDE Leiden} Amsterdam Center for Drug Research, Department of Pharmacochemistry, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
,
J. M. te KOPPELE Leiden} Amsterdam Center for Drug Research, Department of Pharmacochemistry, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
&
N. P. E. VERMEULEN Leiden} Amsterdam Center for Drug Research, Department of Pharmacochemistry, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
Pages 855-875 | Published online: 22 Sep 2008

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Jos G. M. Bessems & Nico P. E. Vermeulen. (2001) Paracetamol (Acetaminophen)-Induced Toxicity: Molecular and Biochemical Mechanisms, Analogues and Protective Approaches. Critical Reviews in Toxicology 31:1, pages 55-138.
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Articles from other publishers (19)

Liu Liu, Fangjie Guo, Hongyang Cui, Li Ji, Yi Yang, Ling Jiao, Yixuan Huang & Yi Wan.. (2024) Alkylphenols disrupt estrogen homeostasis via diradical cross-coupling reactions: A novel pathway of endocrine disruption. Environment International 183, pages 108428.
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Rajesh Kumar, Raksha Rani, Sanjay Kumar Narang, Seema Rai & Younis Ahmad Hajam. 2021. Phytomedicine. Phytomedicine 621 653 .
Maranda Esterhuizen-Londt, Katrin Schwartz & Stephan Pflugmacher. (2016) Using aquatic fungi for pharmaceutical bioremediation: Uptake of acetaminophen by Mucor hiemalis does not result in an enzymatic oxidative stress response. Fungal Biology 120:10, pages 1249-1257.
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Rosivaldo S. Borges, Gláucio R. Nagurniak, Luana M. D. Queiroz, Cristiane S. F. Maia, Carlos A. L. Barros, Ednilsom Orestes & Albérico B. F. da Silva. (2015) Structure and toxicity of clozapine and olanzapine on agranulocytosis. Medicinal Chemistry Research 25:2, pages 322-328.
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Ivana Klopčič, Matic Poberžnik, Janez Mavri & Marija Sollner Dolenc. (2015) A quantum chemical study of the reactivity of acetaminophen (paracetamol) toxic metabolite N-acetyl-p-benzoquinone imine with deoxyguanosine and glutathione. Chemico-Biological Interactions 242, pages 407-414.
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Li Ji & Gerrit Schüürmann. (2015) Computational Biotransformation Profile of Paracetamol Catalyzed by Cytochrome P450. Chemical Research in Toxicology 28:4, pages 585-596.
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Rasmus Leth, Patrik Rydberg, Flemming Steen Jørgensen & Lars Olsen. (2015) Density Functional Theory Study on the Formation of Reactive Benzoquinone Imines by Hydrogen Abstraction. Journal of Chemical Information and Modeling 55:3, pages 660-666.
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Patric Schyman, Wenzhen Lai, Hui Chen, Yong Wang & Sason Shaik. (2011) The Directive of the Protein: How Does Cytochrome P450 Select the Mechanism of Dopamine Formation?. Journal of the American Chemical Society 133:20, pages 7977-7984.
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R. Santos Borges, A. P. Salgado Mendes, B. H. Souza e Silva, C. Nahum Alves & J. L. Martins do Nascimento. (2010) A theoretical study of salicylate oxidation for ADME prediction. Medicinal Chemistry Research 20:3, pages 269-273.
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M.I. González-Sánchez, J. Rubio-Retama, E. López-Cabarcos & E. Valero. (2011) Development of an acetaminophen amperometric biosensor based on peroxidase entrapped in polyacrylamide microgels. Biosensors and Bioelectronics 26:5, pages 1883-1889.
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María I. González-Sánchez, María C. Manjabacas, Francisco García-Carmona & Edelmira Valero. (2009) Mechanism of Acetaminophen Oxidation by the Peroxidase-like Activity of Methemoglobin. Chemical Research in Toxicology 22:11, pages 1841-1850.
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Fengping Li, Mahendra D. Chordia, Tao Huang & Timothy L. Macdonald. (2008) In Vitro Nimesulide Studies toward Understanding Idiosyncratic Hepatotoxicity: Diiminoquinone Formation and Conjugation. Chemical Research in Toxicology 22:1, pages 72-80.
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Amit S. Kalgutkar, James Driscoll, Sabrina X. Zhao, Gregory S. Walker, Richard M. Shepard, John R. Soglia, James Atherton, Linning Yu, Abdul E. Mutlib, Michael J. Munchhof, Lawrence A. Reiter, Christopher S. Jones, Johnathan L. Doty, Kristen A. Trevena, Christopher L. Shaffer & Sharon L. Ripp. (2007) A Rational Chemical Intervention Strategy To Circumvent Bioactivation Liabilities Associated with a Nonpeptidyl Thrombopoietin Receptor Agonist Containing a 2-Amino-4-arylthiazole Motif. Chemical Research in Toxicology 20:12, pages 1954-1965.
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Bernard Testa & Stefanie D. Krämer. (2007) The Biochemistry of Drug Metabolism – An Introduction. Chemistry & Biodiversity 4:3, pages 257-405.
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Deepak Dalvie, Evan Smith, Alan Deese & Stephen Bowlin. (2006) IN VITRO METABOLIC ACTIVATION OF THIABENDAZOLE VIA 5-HYDROXYTHIABENDAZOLE: IDENTIFICATION OF A GLUTATHIONE CONJUGATE OF 5-HYDROXYTHIABENDAZOLE. Drug Metabolism and Disposition 34:4, pages 709-717.
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C. N. Alves, R. S. Borges & A. B. F. Da Silva. (2006) Density functional theory study of metabolic derivatives of the oxidation of paracetamol. International Journal of Quantum Chemistry 106:13, pages 2617-2623.
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Kelem Kassahun, Konstantine Skordos, Ian McIntosh, Donald Slaughter, George A. Doss, Thomas A. Baillie & Garold S. Yost. (2005) Zafirlukast Metabolism by Cytochrome P450 3A4 Produces an Electrophilic α,β-Unsaturated Iminium Species That Results in the Selective Mechanism-Based Inactivation of the Enzyme. Chemical Research in Toxicology 18:9, pages 1427-1437.
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J.E.M. Diniz, R.S. Borges & C.N. Alves. (2004) A DFT study for paracetamol and 3,5-disubstituted analogues. Journal of Molecular Structure: THEOCHEM 673:1-3, pages 93-97.
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E. Valero, R. Varón & F. García-Carmona. (2002) Tyrosinase-Mediated Oxidation of Acetaminophen to 4-Acetamido-o- Benzoquinone. Biological Chemistry 383:12.
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