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Development of Acetylcholinesterase Biosensors for Harmful Substances Detection in Food and Environment

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Development of Acetylcholinesterase Biosensors for Harmful Substances Detection in Food and Environment Development of Acetylcholinesterase biosensors for neurotoxins detection in foods and the environment Entwicklung von Acetylcholinesterase- Biosensoren zur Neurotoxinedetektion in Lebensmitteln und Umwelt Von der Fakultät Chemie der Universität Stuttgart zur Erlangung der Würde eines Doktors der Naturwissenschaften (Dr. rer. nat.) genehmigte Abhandlung Vorgelegt von Clarisse Brüning Schmitt Roepcke Aus Blumenau (Brasilien) Hauptberichter: Prof. Dr. Bernhard Hauer Mitberichter: PD. Dr. Wolfgang Hilt Vorsitzender: Prof. Dr. Bernd J. Plietker Tag der mündlichen Prüfung: 17. Mai 2011 Institut für Technische Biochemie der Universität Stuttgart 2011 2 For my family „In all, three things remain: The certainty that we are always starting… The certainty that we need to continue… The certainty that we will be stopped before the end… Therefore, we must: Turn the break into a new path… The fall into a dance step… The fear into a ladder… The dream, a bridge… The search, a finding…” Fernando Sabino 3 Acknowledgments First of all, I would like to express my deepest sense of gratitude to my PhD supervisor Prof. Dr. Bernhard Hauer for his patient guidance, encouragement and excellent advice throughout this study. I am grateful to Prof. Dr. Rolf D. Schmid, for providing me the opportunity to develop my PhD thesis at the Institute for Technical Biochemistry, close supervision and financial support. I would like to express my gratitude to my Scholarship sponsor, the “Deutscher Akademischer Austausch Dienst” (DAAD), who allowed the financial support of my study during most of its duration. My sincere thanks to Dr. Holger Schulze for his distance collaboration, advice and encouragement throughout the course of the thesis, and for helping me with the correction of my PhD thesis and articles. I owe my deepest gratitude to Dipl.-Ing. Susanne B. Münch, without whom, this thesis would not have been possible. She teached me the techniques that made possible this work, and gave me always practical tips and support. I am also thankful to M. Sc. Sumire Honda Malca, for the help with the SDS-technique, friendship and confort words, and the remembrance that South America was always near. I am grateful to Dr. Holger Beuttler, Dr. Evelyne Weber, Dr. Bernd Nebel, Dipl.-Biol. Björn Mückschel, Dipl.-Ing. Sven Richter, and Dipl.-Biol. Matthias Gunne, for their generous technical assistance during this time. I also thank my colleagues of the Analytical Biotechnology group for sharing unforgettable moments and knowledge during the time of study: Luam, Victoria, Beate, Sandy, Kristina, Thomas, Johanna, Janina, Barbara Schwarz, Barbara Hörmann, Melanie, Sabrina, and Thorsten. I owe my gratitude to all my ITB colleagues for all the good moments I spent in the University of Stuttgart, laughs during the coffee breaks and teaching about the german culture. I am thankful to Mrs. Angelika Inhoffen for her assistance on editing my thesis writing, and for always giving me a friend advice in the bad times. I acknowledge my gratitude to CVUA for their fruitful collaboration, sending food samples for the biosensor analysis, and valuable assistance in the research. Finally, I take this opportunity to express my profound gratitude to my husband Fabricio, for being always at my side, loving me and encouraging me, and to my beloved parents, for their guidance and moral support during all my life. 4 Table of contents ABBREVIATIONS ............................................................................................................................................... 7 ENGLISH SUMMARY ......................................................................................................................................... 9 ZUSAMMENFASSUNG .................................................................................................................................... 11 1. INTRODUCTION ..................................................................................................................................... 18 1.1. BIOSENSORS........................................................................................................................................... 18 1.2. ACETYLCHOLINESTERASE ........................................................................................................................... 20 1.2.1 Acetylcholinesterase from Nippostrongylus brasiliensis ............................................................... 24 1.3. ACETYLCHOLINESTERASE BIOSENSORS .......................................................................................................... 28 1.3.1 Amperometric acetylcholinesterase biosensors ............................................................................ 32 1.4. TYPES OF INHIBITION ................................................................................................................................ 36 1.5. ORGANOPHOSPHATE AND CARBAMATE INSECTICIDES ..................................................................................... 38 1.5.1 Organophosphate and carbamate insecticides used in Brazil ....................................................... 42 1.5.2 Organophosphorothionate insecticides......................................................................................... 47 1.6. CHLOROPEROXIDASE ................................................................................................................................ 49 1.7. GLYCOALKALOIDS .................................................................................................................................... 54 2. OBJECTIVES ........................................................................................................................................... 58 2.1. GENERAL OBJECTIVE ................................................................................................................................ 58 2.2. SPECIFIC OBJECTIVES ............................................................................................................................... 58 3. MATERIAL AND METHODS .................................................................................................................... 59 3.1. MATERIAL ............................................................................................................................................. 59 3.1.1 Chemicals, biochemicals and equipments ..................................................................................... 59 3.1.2 Cultivation medium ....................................................................................................................... 62 3.1.3 Buffer, solutions and antibiotics .................................................................................................... 63 3.1.3.1 Buffers ................................................................................................................................................. 63 3.1.3.2 Solutions .............................................................................................................................................. 64 3.1.3.3 Antibiotics............................................................................................................................................ 65 3.2. METHODS ............................................................................................................................................. 65 3.2.1 Spectrophotometric enzymatic activity determination ................................................................. 65 3.2.1.1 Optical acetylcholinesterase activity assay ......................................................................................... 65 3.2.1.2 Optical chloroperoxidase activity assay ............................................................................................... 67 3.2.1.3 Bimolecular rate constant (ki) .............................................................................................................. 68 3.2.2 Determination of the protein concentration ................................................................................. 70 3.2.3 Acetylcholinesterase biosensor test for food samples ................................................................... 70 3.2.3.1 Production of biosensors using screen printing method ..................................................................... 70 3.2.3.1.1 Basic acetylcholinesterase biosensor production .......................................................................... 70 3.2.3.1.2 Working electrode (TCNQ-graphite) .............................................................................................. 72 3.2.3.1.3 Acetylcholinesterase printing paste ............................................................................................... 72 3.2.3.2 Samples preparation ........................................................................................................................... 73 3.2.3.2.1 Chemical oxidation of organophosphorothionates in buffer solution ........................................... 73 3.2.3.2.2 Chemical oxidation of organophosphorothionates in food samples.............................................. 73 3.2.3.3 Acetylcholinesterase biosensor measurement.................................................................................... 73 3.2.3.3.1 Acetylcholinesterase biosensors measurement tests for insecticide detection ............................ 73 3.2.3.3.2 Detection limit of the biosensors ..................................................................................................
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