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Xenobiotica
the fate of foreign compounds in biological systems
Volume 20, 1990 - Issue 7
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Original Article

Development of a 19F-n.m.r. method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline

J. Vervoort Department of Biochemistry, Agricultural University, Dreijenlaan 3, 6703 HA, Wageningen, The Netherlands
,
P. A. De Jager Department of Molecular Physics, Agricultural University, Dreijenlaan 3, 6703 HA, Wageningen, The Netherlands
,
J. Steenbergen Department of Biochemistry, Agricultural University, Dreijenlaan 3, 6703 HA, Wageningen, The Netherlands
&
I. M. C. M. Rietjens Department of Biochemistry, Agricultural University, Dreijenlaan 3, 6703 HA, Wageningen, The Netherlands
Pages 657-670 | Received 08 Sep 1989, Accepted 01 Mar 1990, Published online: 27 Aug 2009

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C. J. Duckett, J. C. Lindon, H. Walker, F. Abou-Shakra, I. D. Wilson & J. K. Nicholson. (2006) Metabolism of 3-chloro-4-fluoroaniline in rat using [14C]-radiolabelling, 19F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR. Xenobiotica 36:1, pages 59-77.
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E. M. Lenz, J. C. Lindon, J. K. Nicholson, J. M. Weeks & D. Osborn. (2002) 19 F-NMR and directly coupled 19 F/ 1 H-HPLC-NMR spectroscopic investigations of the metabolism of the model ecotoxin 3-trifluoromethylaniline in the earthworm species Eisenia veneta. Xenobiotica 32:6, pages 535-546.
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J. G. Bundy, E. M. Lenz, D. Osborn, J. M. Weeks, J. C. Lindon & J. K. Nicholson. (2002) Metabolism of 4-fluoroaniline and 4-fluorobiphenyl in the earthworm Eisenia veneta characterized by high-resolution NMR spectroscopy with directly coupled HPLC-NMR and HPLC-MS. Xenobiotica 32:6, pages 479-490.
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Zoja I. Finkelstein, Boris P. Baskunov, Ivonne M. C. M. Rietjens, Marelle G. Boersma, Jacques Vervoort & Ludmila A. Golovleva. (2001) TRANSFORMATION OF THE INSECTICIDE TEFLUBENZURON BY MICROORGANISMS. Journal of Environmental Science and Health, Part B 36:5, pages 559-567.
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M. E. Bollard, E. Holmes, C. A. Blackledge, J. C. Lindon, I. D. Wilson & J. K. Nicholson. (1996) 1H and 19F-nmr spectroscopic studies on the metabolism and urinary excretion of mono- and disubstituted phenols in the rat. Xenobiotica 26:3, pages 255-273.
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A. E. M. F. Soffers, C. Veeger & I. M. C. M. Rietjens. (1994) Influence of the type of halogen substituent on in vivo and in vitro phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes. Xenobiotica 24:8, pages 759-774.
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S. Boeren, B. Tyrakowska, J. Vervoort, E. de Hoffman, K. Teunis, A. Van Veldhuizen & I. M. C. M. Rietjens. (1992) Rat liver microsomal metabolism of 2-halogenated 4-methylanilines. Xenobiotica 22:12, pages 1403-1423.
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Articles from other publishers (25)

Mariëlle J. H. Moonen, Nanne M. Kamerbeek, Adrie H. Westphal, Sjef A. Boeren, Dick B. Janssen, Marco W. Fraaije & Willem J. H. van Berkel. (2008) Elucidation of the 4-Hydroxyacetophenone Catabolic Pathway in Pseudomonas fluorescens ACB . Journal of Bacteriology 190:15, pages 5190-5198.
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Mariëlle J. H. Moonen, Adrie H. Westphal, Ivonne M. C. M. Rietjens & Willem J. H. van Berkel. (2005) Enzymatic Baeyer-Villiger Oxidation of Benzaldehydes. Advanced Synthesis & Catalysis 347:7-8, pages 1027-1034.
Crossref
E.M. Lenz, J.C. Lindon, J.K. Nicholson, J.M. Weeks & D. Osborn. (2003) 19F NMR spectroscopic investigation into the absorption and metabolism of 3-trifluoromethylaniline in Eisenia veneta. Ecotoxicology and Environmental Safety 54:2, pages 157-168.
Crossref
Francesc X. Prenafeta-Boldú, Dion M. A. M. Luykx, Jacques Vervoort & Jan A. M. de Bont. (2001) Fungal Metabolism of Toluene: Monitoring of Fluorinated Analogs by 19 F Nuclear Magnetic Resonance Spectroscopy . Applied and Environmental Microbiology 67:3, pages 1030-1034.
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Zoya I. Finkelstein, Boris P. Baskunov, Marelle G. Boersma, Jacques Vervoort, Eugene L. Golovlev, Willem J. H. van Berkel, Ludmila A. Golovleva & Ivonne M. C. M. Rietjens. (2000) Identification of Fluoropyrogallols as New Intermediates in Biotransformation of Monofluorophenols in Rhodococcus opacus 1cp . Applied and Environmental Microbiology 66:5, pages 2148-2153.
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Vladimir S. Bondar, Marelle G. Boersma, Willem J.H. Berkel, Zoya I. Finkelstein, Eugene L. Golovlev, Boris P. Baskunov, Jacques Vervoort, Ludmila A. Golovleva & Ivonne M.C.M. Rietjens. (1999) Preferential oxidative dehalogenation upon conversion of 2-halophenols by Rhodococcus opacus 1G . FEMS Microbiology Letters 181:1, pages 73-82.
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Janneke Koerts, Ans E. M. F. Soffers, Jacques Vervoort, Adrie De Jager & Ivonne M. C. M. Rietjens. (1998) Occurrence of the NIH Shift upon the Cytochrome P450-Catalyzed in Vivo and in Vitro Aromatic Ring Hydroxylation of Fluorobenzenes. Chemical Research in Toxicology 11:5, pages 503-512.
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Marelle G. Boersma, Tatiana Y. Dinarieva, Wouter J. Middelhoven, Willem J. H. van Berkel, Joel Doran, Jacques Vervoort & Ivonne M. C. M. Rietjens. (1998) 19 F Nuclear Magnetic Resonance as a Tool To Investigate Microbial Degradation of Fluorophenols to Fluorocatechols and Fluoromuconates . Applied and Environmental Microbiology 64:4, pages 1256-1263.
Crossref
Ahmed M Osman, Sjef Boeren, Cees Veeger & Ivonne M.C.M Rietjens. (1997) MP8-dependent oxidative dehalogenation: evidence for the direct formation of 1,4-benzoquinone from 4-fluorophenol by a peroxidase-type of reaction pathway. Chemico-Biological Interactions 104:2-3, pages 147-164.
Crossref
Janneke Koerts, Martine M. C. Velraeds, Ans E. M. F. Soffers, Jacques Vervoort & Ivonne M. C. M. Rietjens. (1997) Influence of Substituents in Fluorobenzene Derivatives on the Cytochrome P450-Catalyzed Hydroxylation at the Adjacent Ortho Aromatic Carbon Center. Chemical Research in Toxicology 10:3, pages 279-288.
Crossref
Ahmed M. Osman, Janneke Koerts, Marelle G. Boersma, Sjef Boeren, Cees Veeger & Ivonne M. C. M. Rietjens. (2004) Microperoxidase/H 2 O 2 ‐Catalyzed Aromatic Hydroxylation Proceeds by a Cytochrome‐ P ‐450‐Type Oxygen‐Transfer Reaction Mechanism . European Journal of Biochemistry 240:1, pages 232-238.
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Bożena Tyrakowska, Nicole H.P. Cnubben, Ans E.M.F. Soffers, Th. Wobbes & Ivonne M.C.M. Rietjens. (1996) Comparative MO-QSAR studies in various species including man. Chemico-Biological Interactions 100:2, pages 187-201.
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Ans E. M. F. Soffers, Jan H. T. M. Ploemen, Mariëlle J. H. Moonen, Theo Wobbes, Ben van Ommen, Jacques Vervoort, Peter J. van Bladeren & Ivonne M. C. M. Rietjens. (1996) Regioselectivity and Quantitative Structure−Activity Relationships for the Conjugation of a Series of Fluoronitrobenzenes by Purified Glutathione S -Transferase Enzymes from Rat and Man . Chemical Research in Toxicology 9:3, pages 638-646.
Crossref
Janneke Koerts, Sjef Boeren, Jacques Vervoort, Raymond Weiss, Cees Veeger & Ivonne M.C.M. Rietjens. (1996) Interaction between the substrate and the high-valent-iron-oxo porphyrin cofactor as a possible factor influencing the regioselectivity of cytochrome P450 catalysed aromatic ring hydroxylation of 3-fluoro(methyl)anilines. Chemico-Biological Interactions 99:1-3, pages 129-146.
Crossref
H.E.M.G. Haenen, I.M.C.M. Rietjens, J. Vervoort, J.H.M. Temmink & P.J. van Bladeren. (1995) In vitro metabolism of 5-fluoro-2-glutathionyl-nitrobenzene by kidney proximal tubular cells studied by 19F-NMR. Chemico-Biological Interactions 98:2, pages 97-112.
Crossref
Nicole H.P. Cnubben, Jacques Vervoort, Marelle G. Boersma & Ivonne M.C.M. Rietjens. (1995) The effect of varying halogen substituent patterns on the cytochrome P450 catalysed dehalogenation of 4-halogenated anilines to 4-aminophenol metabolites. Biochemical Pharmacology 49:9, pages 1235-1248.
Crossref
Ivonne M.C.M. Rietjens, Nicole H.P. Cnubben, Marjon van Haandel, Bozena Tyrakowska, Ans E.M.F. Soffers & Jacques Vervoort. (1995) Different metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene compared to molecular orbital substrate characteristics. Chemico-Biological Interactions 94:1, pages 49-72.
Crossref
Cathaline den Besten, Marjon M.H. Bennik, Marlou van Iersel, Maria A.W. Peters, Cees Teunis & Peter J. van Bladeren. (1994) Comparison of the urinary metabolite profiles of hexachlorobenzene and pentachlorobenzene in the rat. Chemico-Biological Interactions 90:2, pages 121-137.
Crossref
J.T. Gerig. (1994) Fluorine NMR of proteins. Progress in Nuclear Magnetic Resonance Spectroscopy 26, pages 293-370.
Crossref
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.
Crossref
N.H.P. Cnubben, J. Vervoort, C. Veeger & I.M.C.M. Rietjens. (1992) Study on the regioselectivity and mechanism of the aromatic hydroxylation of monofluoroanilines. Chemico-Biological Interactions 85:2-3, pages 151-172.
Crossref
A.R Jacobson, L.A Sylvia, D.L Veenstra & J.T Gerig. (1992) 19F[1H] NOE determinations in surface-coil experiments. Journal of Magnetic Resonance (1969) 96:2, pages 387-392.
Crossref
J. Vervoort, I. M. C. M. Rietjens, C. T. W. Moonen, M. Von Kienlin & D. Despres. (1991) Biotransformation of 2-fluoroaniline in rats studied byIn Vivo19F NMR. NMR in Biomedicine 4:6, pages 255-261.
Crossref
I.M.C.M. Rietjens & J. Vervoort. (1991) Bioactivation of 4-fluorinated anilines to benzoquinoneimines as primary reaction products. Chemico-Biological Interactions 77:3, pages 263-281.
Crossref
I. M. C. M. Rietjens, J. Koerts, S. Boeren & J. Vervoort. (2010) Biosynthesis and chemical determination of polyfluoro-4-hydroxyanilines. Recueil des Travaux Chimiques des Pays-Bas 110:5, pages 216-221.
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