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Research Article

Inactivation of Cytochrome P-450 and Monoamine Oxidase by Cyclopropylamines

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Pages 1163-1182 | Received 16 Aug 1982, Accepted 21 Nov 1983, Published online: 22 Sep 2008

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Vincent C.O. Njar, JÖRg Düerkop & Rolf W. Hartmann. (1995) Novel 19-(Cyclopropylamino)-Androst-4-EN-3,17-Dione: a Mechanism-Based Inhibitor of Aromatase. Journal of Enzyme Inhibition 10:1, pages 47-56.
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Yu Zhang, Yuan Li, Wei Zhou, Mengru Zhang, Qian Zhang, Ran Jia & Jinbo Zhao. (2020) Assembly of polysubstituted chiral cyclopropylamines via highly enantioselective Cu-catalyzed three-component cyclopropene alkenylamination . Chemical Communications 56:81, pages 12250-12253.
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Richard B. Silverman & Mark W. Holladay. 2014. The Organic Chemistry of Drug Design and Drug Action. The Organic Chemistry of Drug Design and Drug Action 357 422 .
Senait Ghirmai, Marc R. Azar & John R. Cashman. (2009) Synthesis and pharmacological evaluation of 6-naltrexamine analogs for alcohol cessation. Bioorganic & Medicinal Chemistry 17:18, pages 6671-6681.
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Andrew Mamantov. (2008) Possible New Reaction Mechanisms of Dideoxynucleosides as Anti-Aids Drugs. Progress in Reaction Kinetics and Mechanism 33:2, pages 99-143.
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Senait Ghirmai, Marc R. Azar, Wilma E. Polgar, Ilona Berzetei-Gurske & John R. Cashman. (2008) Synthesis and Biological Evaluation of α- and β-6-Amido Derivatives of 17-Cyclopropylmethyl-3, 14β-dihydroxy-4, 5α-epoxymorphinan: Potential Alcohol-Cessation Agents. Journal of Medicinal Chemistry 51:6, pages 1913-1924.
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Wolfgang Knolle, Igor Janovský, Sergej Naumov & Ffrancon Williams. (2006) EPR Studies of Amine Radical Cations. Part 2. Thermal and Photo-Induced Rearrangements of Propargylamine and Allylamine Radical Cations in Low-Temperature Freon Matrices. The Journal of Physical Chemistry A 110:51, pages 13816-13826.
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Thomas M. Polasek, David J. Elliot, Andrew A. Somogyi, Elizabeth M. J. Gillam, Benjamin C. Lewis & John O. Miners. (2006) An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. British Journal of Clinical Pharmacology 61:5, pages 570-584.
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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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I. Janovský, W. Knolle, S. Naumov & F. Williams. (2004) EPR Studies of Amine Radical Cations, Part 1: Thermal and Photoinduced Rearrangements of n -Alkylamine Radical Cations to their Distonic Forms in Low-Temperature Freon Matrices . Chemistry - A European Journal 10:21, pages 5524-5534.
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Richard B. Silverman. 2004. The Organic Chemistry of Drug Design and Drug Action. The Organic Chemistry of Drug Design and Drug Action 405 495 .
E Vaccaro, M Giorgi, V Longo, G Mengozzi & P.G Gervasi. (2003) Inhibition of cytochrome P450 enzymes by enrofloxacin in the sea bass (Dicentrarchus labrax). Aquatic Toxicology 62:1, pages 27-33.
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Kandatege Wimalasena, Heang B. Wickman & Mathew P. D. Mahindaratne. (2001) Autocatalytic Radical Ring Opening ofN-Cyclopropyl-N-phenylamines Under Aerobic Conditions − Exclusive Formation of the Unknown Oxygen Adducts,N-(1,2-Dioxolan-3-yl)-N-phenylamines. European Journal of Organic Chemistry 2001:20, pages 3811-3817.
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Gouhua Zhao, Junya Qu, Franklin A. Davis & Marilyn Schuman Jorns. (2000) Inactivation of Monomeric Sarcosine Oxidase by Reaction with N -(Cyclopropyl)glycine . Biochemistry 39:46, pages 14341-14347.
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Michael C. Pirrung, Jun Cao & Jrlung Chen. (1998) Ethylene biosynthesis: processing of a substrate analog supports a radical mechanism for the ethylene-forming enzyme. Chemistry & Biology 5:1, pages 49-57.
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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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G KlopmanD FercuT E RenauM R Jacobs. (1996) N-1-tert-butyl-substituted quinolones: in vitro anti-Mycobacterium avium activities and structure-activity relationship studies. Antimicrobial Agents and Chemotherapy 40:11, pages 2637-2643.
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G. Klopman, D. Fercu, J.-Y. Li, H.s. Rosenkranz & M.R. Jacobs. (1996) Antimycobacterial quinolones: a comparative analysis of structure-activity and structure-cytotoxicity relationships. Research in Microbiology 147:1-2, pages 86-96.
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Paul R. Ortiz de Montellano. 1995. Cytochrome P450. Cytochrome P450 245 303 .
G Klopman, J Y Li, S Wang, A J Pearson, K Chang, M R Jacobs, S Bajaksouzian & J J Ellner. (1994) In vitro anti-Mycobacterium avium activities of quinolones: predicted active structures and mechanistic considerations.. Antimicrobial Agents and Chemotherapy 38:8, pages 1794-1802.
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Ludger Wessjohann, Norbert Krass, Dahai Yu & Armin De Meijere. (2006) A New Versatile Synthesis of Ring‐Substituted 2‐Cyclopropylglycines and Related Amino Acids. Chemische Berichte 125:4, pages 867-882.
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W. A. Van Sickle, M. R. Angelastro, P. Wilson, J. R. Cooper, A. Marquart & M. A. Flanagan. (1992) Inhibition of cholesterol synthesis by cyclopropylamine derivatives of squalene in human hepatoblastoma cells in culture. Lipids 27:3, pages 157-160.
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L R Hall & R P Hanzlik. (1990) Kinetic deuterium isotope effects on the N-demethylation of tertiary amides by cytochrome P-450.. Journal of Biological Chemistry 265:21, pages 12349-12355.
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Gun Il Kang & Suk Kil Hong. (1990) Quantitative structure-activity relationships in MAO-inhibitory 2-phenylcyclopropylamines: Insights into the topography of MAO-A and MAO-B. Archives of Pharmacal Research 13:1, pages 82-96.
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Pawel Kolodziejczyk & J. William Lown. 1990. Antioxidants in Therapy and Preventive Medicine. Antioxidants in Therapy and Preventive Medicine 323 338 .
Michael R. Angelastro, Marie E. Laughlin, Gerald L. Schatzman, Philippe Bey & Thomas R. Blohm. (1989) 17β-(Cyclopropylamino)-androst-5-en-3β-ol, a selective mechanism-based inhibitor of cytochrome P45017α (steroid 17α-hydroxylase/C17–20 lyase). Biochemical and Biophysical Research Communications 162:3, pages 1571-1577.
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L. Shaw, M.S. Lennard, G.T. Tucker, N.D.S. Bax & H.F. Woods. (1987) Irreversible binding and metabolism of propranolol by human liver microsomes—Relationship to polymorphic oxidation. Biochemical Pharmacology 36:14, pages 2283-2288.
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Gun Il Kang, Suk Kil Hong & Hee Kyung Choi. (1987) 1-methyl substituent and stereochemical effects of 2-phenylcyclopropylamines on the inhibition of rat brain mitochondrial monoamine oxidase A and B. Archives of Pharmacal Research 10:1, pages 50-59.
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Paul R. Ortiz de Montellano. 1986. Cytochrome P-450. Cytochrome P-450 217 271 .

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