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Mechanic Aspects and Parameters for Biological Effect Monitoring Erythrotoxicity of aliphatic hydroxylamines : mechanic aspects and parameters for biological effect monitoring Citation for published version (APA): Spooren, A. A. M. G. (2000). Erythrotoxicity of aliphatic hydroxylamines : mechanic aspects and parameters for biological effect monitoring. UM. https://doi.org/10.26481/dis.20001026as Document status and date: Published: 01/01/2000 DOI: 10.26481/dis.20001026as Document Version: Publisher's PDF, also known as Version of record Please check the document version of this publication: • A submitted manuscript is the version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. 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Link to publication General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal. If the publication is distributed under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license above, please follow below link for the End User Agreement: www.umlib.nl/taverne-license Take down policy If you believe that this document breaches copyright please contact us at: [email protected] providing details and we will investigate your claim. Download date: 09 Oct. 2021 OOOS noofeofef .rwKKjqS ,0 y A.A '. .;:-• • •' .•.•.•j.t';-:-.--:!*-v;snsfflyri\e-- Erythrotoxicity of Aliphatic Hydroxylamines Mechanistic aspects and parameters for biological effect monitoring © A.A.M.G. Spooren, Montfoort 2000 ISBN 90-9014120-0 Subject headings: hydroxylamines / human erythrocytes / toxicology All rights reserved. No part of this thesis may be reproduced in any form or by any means without permission of the holder of the copyright. Financial support by the Saal van Zwanenberg foundation and the dr. ir. J.H. J. van der Laar foundation for the advancement of biochemical research for the publication of this thesis is gratefully acknowledged. tail Erythrotoxicity of Aliphatic Hydroxylamines * Mechanistic aspects and parameters =•3 for biological effect monitoring OtWiH .'i.-l.H ,id PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Universiteit Maastricht, op gezag van de Rector Magnificus, Prof. dr. A.C. Nieuwenhuijzen Kruseman, volgens het besluit van het College van Dekanen, in het openbaar te verdedigen op donderdag 26 oktober 2000 om 14.00 uur door Antonette Allegonda Maria Gerarda Spooren geboren te Vught op 1 april 1968 Promotores: Prof. Dr. H.A.J. Struijker Boudier Prof. Dr. A. Bast Co-promotor: Dr. ir. C.T.A. Evelo Beoordelingscommissie: •„._,,. ,. Prof. Dr. M.P. van Dieijen-Visser (voorzitter) Dr. B.J. Blaauboer (Universiteit Utrecht) Prof. Dr. P.J. van Bladeren (Wageningen Universiteit) Prof. Dr. H.F.P. Hillen De ivaarne/d /s ze/den zu/Ver en noo/f eenvoud/g Oscar Wilde Contents Abbreviations used 9 Chapter 1 General Introduction 11 Chapter 2 Two mechanisms for toxic effects of hydroxylamine in human erythrocytes: Involvement of free radicals and risk of potentiation 41 Chapter 3 In vitro hematotoxic effects of three methylated hydroxylamines 59 Chapter 4 Only the glutathione dependent antioxidant enzymes are inhibited by hematotoxic hydroxylamines 67 Chapter 5 Hydroxylamine treatment increases glutathione-protein and protein-protein binding in human erythrocytes • 75 Chapter 6 A study on the interaction between hydroxylamine analogues and oxyhemoglobin in intact erythrocytes 91 Chapter 7 Occupational handling of O-methyl hydroxylamine: adoption of an integrated strategy for risk prevention 111 Chapter 8 General discussion and conclusions 127 Chapter 9 Summary 139 Chapter 10 Samenvatting 143 Dankwoord 147 Curriculum Vitae 149 List of Publications 151 3 Ins! not Abbreviations used ADP Andenine diphosphate ATP Adenine triphosphate BEM Biological effect monitoring CDNB 1-chloro-2,4-dinitrobenzene CO Carbon monoxide CPD Citrate-phosphate-dextrose DPG Diphosphoglycerate DTT Dithiothreitol DTNB 5,5'-dithio-bis(2-nitrobenzoic acid) EC-SOD Extracellular superoxide dismutase EDTA Ethylenediaminetetraacetic acid FAD Flavin adenine dinucleotide Fe** Ferrous iron Fe^ Ferric iron G6P Glucose 6-phosphate G6PDH Glucose 6-phosphate dehydrogenase GPX Glutathione peroxidase GR Glutathione reductase GRcoeff Glutathione reductase riboflavin activity coefficient GS' Thiyl radical GSH Glutathione (reduced) GSOO' Peroxysulphenyl radical GSSG Glutathione (oxidized) GST Glutathione S-transferase GT Glutathione (total) H2O2 Hydrogen peroxide Hb Hemoglobin Hb* Methemoglobin HbSH Free sulfhydryl groups in hemoglobin HbS-SG Hemogobin-hemoglobin mixed disulfides HbS-SHb Hemoglobin-glutathione mixed disulfides HYAM Hydroxylamine LDL Low-density lipoprotein LP Lipid peroxidation MAC Maximum acceptable concentration MDA Malondialdehyde Mem ProtS-SG Membrane protein-hemoglobin mixed disulfides Mem ProtS-SHb Membrane protein-glutathion mixed disulfides MHbR NADPH methemoglobin reductase 10 Abbrew'af/ons used MW Molecular weight j 11ti • \; « j MA NADH P-nicotinamide adenine dinucleotide (reduced) NADH-HbR NADH methemoglobin reductase NADPH P-nicotinamide adenine dinucleotide phosphate (reduced) NADPH-HbR NADPH methemoglobin reductase NF-KB Nuclear factor KB NO Nitric oxide NDMH N-dimethyl hydroxylamine NMH N-methyl hydroxylamine NODMH N,O-dimethyl hydroxylamine Singlet oxygen Superoxide radical OH* Hydroxyl radical OEH O-ethyl hydroxylamine OMH O-methyl hydroxylamine 6PGDH 6-phosphogluconate dehydrogenase PBS Phosphate-buffered saline SD Standard deviation SDS-PAGE Sodium dodecyl sulphate polyacrylamide gel electrophoresis Se Selenium SE Standard error SEMD Standard error of the mean difference SH Sulfhydryl groups SOD Superoxide dismutase STEL Short-term exposure limits TBA Thiobarbituric acid TBARS Thiobarbituric acid reactive substances TCA Trichloroacetic acid TLV Threshold limit values TLV-C Threshold limit value ceiling TT Thioltransferase TWA Time weighted average Chapteri • • ••• • •• •-•• • - - "• ; -^••-' '•";/"" ^ General Introduction I I ^, Toxicology is the study of the adverse effects of chemicals on living organisms. The toxicologist is specially trained to examine the nature of these adverse effects and to assess the probability of their occurrence. The combination of a variety of potential adverse effects and the diversity of chemicals present in our environment makes toxicology a very broad science [77]. Therefore, toxicologists are usually specialised to work in one area of toxicology. As occupational toxicologists we are concerned with the prevention of health impairments in workers who may be exposed to industrial chemicals. The working environment may present the risk of workers' overexposure to various chemicals. It is obvious that the control of these risks cannot wait until epidemiological studies have defined the no-adverse-effect level in man. However, extrapolation from animal data or even from human tissue data also has its limitations. Man is not a big rodent and is more than a jigsaw puzzle of tissue fragments. To overcome this problem, toxicity studies in animals and human tissue can be combined with insights in structure activity relationships. As a next step monitoring techniques can be used to check exposure levels and for early evaluation of effects that occur during actual use of a compound in the industry. Monitoring activities has an important role in occupational and environmental practice. Most obvious are the methods related to the evaluation of the presence of chemical agents either in the contaminated environment or in the exposed organism. In the first case the procedures are indicated as environmental monitoring, and in the latter case the procedures are defined as biological monitoring [41]. Lately the arsenal of monitoring techniques has been extended with test methods directed to the assessment of early, possibly reversible, biological effects (biological effect monitoring). In order to use such effects for monitoring, the relationship to health impairment does not need to be established. The proposal of tests capable of detecting early adverse biological effects of industrial chemicals requires a detailed knowledge of their mechanism of action. Unfortunately, for many chemicals, such information is still missing. In such cases, the available screening tests are frequently too insensitive for detecting health effects at a reversible stage. Further fundamental research on the mechanism of action of industrial chemicals is needed for development of more useful health surveillance procedures for workers [77]. In this thesis the attention is directed to the toxicity of aliphatic hydroxylamines. Several derivatives of the parent compound hydroxylamine
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