240
Views
35
CrossRef citations to date
0
Altmetric
Research Article

N-OXIDATIVE TRANSFORMATION OF FREE AND N-SUBSTITUTED AMINE FUNCTIONS BY CYTOCHROME P450 AS MEANS OF BIOACTIVATION AND DETOXICATION

Pages 451-477 | Published online: 25 Jul 2002

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (2)

Shufeng Zhou, Eli Chan, Wei Duan, Min Huang & Yu-Zong Chen. (2005) Drug Bioactivation Covalent Binding to Target Proteins and Toxicity Relevance. Drug Metabolism Reviews 37:1, pages 41-213.
Read now

Articles from other publishers (33)

Qi Lian, Jinke Chen, Kaipeng Huang, Keqiang Hou, Jiansong Fang, Wentao Wei & Jingwei Zhou. (2023) Alkali-Driven Photoinduced N-Dealkylation of Aryl Tertiary Amines and Amides. Organic Letters 25:46, pages 8387-8392.
Crossref
Lu-Lu Liu, Li-Xin Wang, Min Peng, Jing Xiang, Huan Yang, Shek-Man Yiu & Tai-Chu Lau. (2023) Ring Nitrogenation of Aromatic Amines by the Excited State of an Osmium(VI) Nitrido Complex. Inorganic Chemistry 62:4, pages 1447-1454.
Crossref
Martyna Cybularczyk‐Cecotka, Agnieszka Kamińska, Zuzanna Jopek & Maciej Giedyk. (2022) Light‐Induced Dealkylation of Benzamides in Aqueous Solution. European Journal of Organic Chemistry 2022:42.
Crossref
Joan Zapiter, Jeffrey R. Harmer, Michel Struwe, Axel Scheidig, Bernd Clement & Paul V. Bernhardt. (2022) Enzyme Electrode Biosensors for N -Hydroxylated Prodrugs Incorporating the Mitochondrial Amidoxime Reducing Component . Analytical Chemistry 94:25, pages 9208-9215.
Crossref
Palraj Kalimuthu, Jeffrey R. Harmer, Milena Baldauf, Ahmed H. Hassan, Tobias Kruse & Paul V. Bernhardt. (2022) Electrochemically driven catalysis of the bacterial molybdenum enzyme YiiM. Biochimica et Biophysica Acta (BBA) - Bioenergetics 1863:3, pages 148523.
Crossref
Shihaozhi Wang, Jiale Yang, Dianjun Li & Jinhui Yang. (2021) Copper‐Catalyzed Cascade N‐Dealkylation/N‐Methyl Oxidation of Aromatic Amines by Using TEMPO and Oxygen as Oxidants. European Journal of Organic Chemistry 2021:48, pages 6768-6772.
Crossref
M. Saeed Mirzaei, Maxim V. Ivanov, Avat Arman Taherpour & Saber Mirzaei. (2021) Mechanism-Based Inactivation of Cytochrome P450 Enzymes: Computational Insights. Chemical Research in Toxicology 34:4, pages 959-987.
Crossref
Xuewen Yi, Siyu Lei, Wangsheng Liu, Fengrui Che, Chunzheng Yu, Xuesong Liu, Zonghua Wang, Xin Zhou & Yuexia Zhang. (2020) Copper-Catalyzed Radical N-Demethylation of Amides Using N -Fluorobenzenesulfonimide as an Oxidant . Organic Letters 22:12, pages 4583-4587.
Crossref
F. Peter Guengerich. 2020. Comprehensive Natural Products III. Comprehensive Natural Products III 96 113 .
Przemysław M. Płonka. 2019. Electron Spin Resonance Spectroscopy in Medicine. Electron Spin Resonance Spectroscopy in Medicine 189 221 .
Christian KubitzaFlorian BittnerCarsten Ginsel, Antje Havemeyer, Bernd Clement & Axel J. Scheidig. (2018) Crystal structure of human mARC1 reveals its exceptional position among eukaryotic molybdenum enzymes. Proceedings of the National Academy of Sciences 115:47, pages 11958-11963.
Crossref
Liuqing Xiao, Yuxing Huang, Yu Luo, Bo Yang, Yizhen Liu, Xuechang Zhou & Junmin Zhang. (2018) Organic Cotton Photocatalysis. ACS Sustainable Chemistry & Engineering 6:11, pages 14759-14766.
Crossref
Ritwika Ray, Arijit Singha Hazari, Shubhadeep Chandra, Debabrata Maiti & Goutam Kumar Lahiri. (2017) Highly Selective Ruthenium‐Catalyzed Direct Oxygenation of Amines to Amides. Chemistry – A European Journal 24:5, pages 1067-1071.
Crossref
Guolin Wu, Yazhen Li, Xuemei Yu, Yu Gao & Haijun Chen. (2017) Acetic Acid Accelerated Visible-Light Photoredox Catalyzed N -Demethylation of N,N -Dimethylaminophenyl Derivatives . Advanced Synthesis & Catalysis 359:4, pages 687-692.
Crossref
Alan Polnariev. 2016. A Worldwide Yearly Survey of New Data in Adverse Drug Reactions. A Worldwide Yearly Survey of New Data in Adverse Drug Reactions 143 151 .
Signe T. Seger, Patrik Rydberg & Lars Olsen. (2015) Mechanism of the N-Hydroxylation of Primary and Secondary Amines by Cytochrome P450. Chemical Research in Toxicology 28:4, pages 597-603.
Crossref
Alan Polnariev. 2015. A worldwide yearly survey of new data in adverse drug reactions. A worldwide yearly survey of new data in adverse drug reactions 185 194 .
F. Peter Guengerich. 2015. Cytochrome P450. Cytochrome P450 523 785 .
Li Ji & Gerrit Schüürmann. (2012) Model and Mechanism: N‐Hydroxylation of Primary Aromatic Amines by Cytochrome P450. Angewandte Chemie International Edition 52:2, pages 744-748.
Crossref
Li Ji & Gerrit Schüürmann. (2012) Modell und Mechanismus: N‐Hydroxylierung primärer aromatischer Amine durch Cytochrom P450. Angewandte Chemie 125:2, pages 772-776.
Crossref
Patrik Rydberg & Lars Olsen. (2011) Do Two Different Reaction Mechanisms Contribute to the Hydroxylation of Primary Amines by Cytochrome P450?. Journal of Chemical Theory and Computation 7:10, pages 3399-3404.
Crossref
Yoffi Segall. (2010) Biomimetic Chemistry as a Useful Tool for Studying Reactive Metabolites of Pesticides. Journal of Agricultural and Food Chemistry 59:7, pages 2845-2856.
Crossref
Frank Hollmann, Isabel W. C. E. Arends, Katja Buehler, Anett Schallmey & Bruno Bühler. (2011) Enzyme-mediated oxidations for the chemist. Green Chem. 13:2, pages 226-265.
Crossref
Max J. Cryle, Stephen G. BellIlme Schlichting. (2010) Structural and Biochemical Characterization of the Cytochrome P450 CypX (CYP134A1) from Bacillus subtilis : A Cyclo- l -leucyl- l -leucyl Dipeptide Oxidase . Biochemistry 49:34, pages 7282-7296.
Crossref
Peter J.H. Scott, Brian G. Hockley, Hank F. Kung, Rajesh Manchanda, Wei Zhang & Michael R. Kilbourn. (2009) Studies into radiolytic decomposition of fluorine-18 labeled radiopharmaceuticals for positron emission tomography. Applied Radiation and Isotopes 67:1, pages 88-94.
Crossref
René Ullrich, Christoph Dolge, Martin Kluge & Martin Hofrichter. (2008) Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita . FEBS Letters 582:29, pages 4100-4106.
Crossref
Dirk Hollmann, Sebastian Bähn, Annegret Tillack & Matthias Beller. (2008) N-Dealkylation of aliphatic amines and selective synthesis of monoalkylated aryl amines. Chemical Communications:27, pages 3199.
Crossref
Peter Hlavica. (2006) Functional interaction of nitrogenous organic bases with cytochrome P450: A critical assessment and update of substrate features and predicted key active-site elements steering the access, binding, and orientation of amines. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1764:4, pages 645-670.
Crossref
Xiao-Xia Yang, Ze-Ping Hu, Sui Yung Chan & Shu-Feng Zhou. (2006) Monitoring drug–protein interaction. Clinica Chimica Acta 365:1-2, pages 9-29.
Crossref
Philippe Bissel & Neal CastagnoliJr.Jr.. (2005) Studies on the cytochrome P450 catalyzed oxidation of 13C labeled 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine by 13C NMR. Bioorganic & Medicinal Chemistry 13:8, pages 2975-2980.
Crossref
Shufeng Zhou, Sui Yung Chan, Boon Cher Goh, Eli Chan, Wei Duan, Min Huang & Howard L McLeod. (2005) Mechanism-Based Inhibition of Cytochrome P450 3A4 by Therapeutic Drugs. Clinical Pharmacokinetics 44:3, pages 279-304.
Crossref
Peter Hlavica. (2004) Models and mechanisms of O‐O bond activation by cytochrome P450. European Journal of Biochemistry 271:22, pages 4335-4360.
Crossref
Shufeng Zhou. (2003) Separation and detection methods for covalent drug–protein adducts. Journal of Chromatography B 797:1-2, pages 63-90.
Crossref

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.