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Biological Activities of Synthetic Coumarin Derivatives

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Biological Activities of Synthetic Coumarin Derivatives Biological Activities of Synthetic Coumarin Derivatives Submitted in partial fulfillment for the Degree of Master of Applied Sciences in Biotechnology in the Department of Biotechnology and Food Technology, Durban University of Technology, Durban, South Africa Kabange Kasumbwe SUPERVISOR: Professor B. Odhav CO- SUPERVISORS: Dr K.N. Venugopala Dr V. Mohanlall REFERENCE DECLARATION I, Mr. Kabange K– 21032182 and Prof Bharti Odhav do hereby declare that in respect of the following dissertation: Title: Biological Activities of Synthetic Coumarin Derivatives 1. As far as we ascertain: a) no other similar dissertation exists; 2. All references as detailed in the dissertation are complete in terms of all personal Communication engaged in and published works consulted. Signature of student Date Signature of supervisor Date Signature of co-supervisor Date Signature of co-supervisor Date AUTHOR’S DECLARATION This study presents original work by the author. It has not been submitted in any form to another academic institution. Where use was made of the work of others, it has been duly acknowledged in the text. The research described in this dissertation was carried out in the Department of Biotechnology and Food Technology, Faculty of Applied Sciences, Durban University of Technology, South Africa, under the supervision of Prof Bharti Odhav, Dr K.N. Venugopala and Dr Viresh Mohanlall ________________ Student’s signature DEDICATION I would like to dedicate this work to the Ilofo`s family : Salima Kahamba Prudence, Jean- Pierre Ilofo, Olivier Ilofo, Joel Ilofo and Christopher Ilofo, you are truly the inspiration of this work and I thank you for your encouragement, support throughout this study. It meant so much to me during the pursuit of my Masters`s degree and I am grateful for all that you have done for me, to each of you I offer my sincere thanks and deepest gratitude. TABLE OF CONTENTS ACKNOWLEDGEMENTS ........................................................................................................ i ABBREVIATIONS .................................................................................................................... ii PUBLICATIONS ...................................................................................................................... iii INTERNATIONAL CONFERENCE PRESENTATIONS .................................................. iii LIST OF FIGURES ................................................................................................................... iv LIST OF TABLES ..................................................................................................................... vi ABSTRACT .............................................................................................................................. vii 1. INTRODUCTION .................................................................................................................. 1 2. LITERATURE REVIEW ..................................................................................................... 4 2.1 Natural coumarins ........................................................................................................................ 4 2.2 Classification of coumarins .......................................................................................................... 5 2.3 Synthesis of coumarins ................................................................................................................. 8 2.3.1 Synthesis of coumarins by Pechmann reaction ....................................................................... 8 2.3.3 Synthesis of coumarin by Perkin Reaction .............................................................................. 9 2.3.4 Synthesis of coumarin by Witting reaction ............................................................................. 9 2.3.5 Biosynthesis pathway of Coumarin ....................................................................................... 10 2.4 Biological activities of coumarins .............................................................................................. 11 2.4.1 Antibacterial activity ............................................................................................................. 11 2.4.2 Antifungal activity ................................................................................................................ 12 2.4.3 Anti-inflammatory activity .................................................................................................... 13 2.4.4 Anti-mosquito activity ........................................................................................................... 13 2.4.5 Antiviral activity .................................................................................................................... 14 2.4.6 Antiadipogenetic Activity ...................................................................................................... 15 2.4.7 Antioxidant activity ............................................................................................................... 16 2.4.8 Safety of coumarin compounds ............................................................................................. 17 2.4.9 Anticancer activity ................................................................................................................. 17 2.4.9.1 Apoptosis (Programmed cell death) .............................................................................................. 18 2.4.9.2 Biochemical pathways ................................................................................................................... 22 3. METHODOLOGY ............................................................................................................. 24 3.1 Overview of the biological screening ......................................................................................... 24 3.2 Synthesic routes of the coumarins used in this study .............................................................. 25 3.3 Synthesis of coumarins CMRN1 - CMRN7 used in this study ............................................... 25 3.3.1 Synthesis of 3-(2-bromoacetyl)-2H-chromen-2-one (CMRN1) ........................................... 25 3.3.2 Synthesis of 6-bromo-3-(2,2-dibromoacetyl) -2H-chromen-2-one (CMRN2) ..................... 26 3.3.3 Synthesis of 3-acetyl-6-bromo-2H-chromen-2-one (CMRN3) ............................................. 26 3.3.4 Synthesis of 6-bromo-3-(2-bromoacetyl) -2H-chromen-2-one (CMRN4) ........................... 26 3.3.5 Synthesis of 3-(2-bromoacetyl) -6-chloro-2H-chromen-2-one (CMRN5)............................ 26 3.3.6 Synthesis of 3-acetyl-6-chloro-2H-chromen-2-one (CMRN6) ............................................. 27 3.3.7 Synthesis of 3-(2-aminothiazol-4-yl)-6-bromo-2H-chromen-2-one (CMRN7) .................... 27 3.4 Biological screening .................................................................................................................... 28 3.4.1 Anti-mosquito activity ........................................................................................................... 28 3.4.1.2 Larvacidal assay ............................................................................................................................ 28 3.4.1.3 Repellency ..................................................................................................................................... 28 3.4.1.4 Animal preparation ........................................................................................................................ 29 3.4.1.5 Insecticidal assay ........................................................................................................................... 30 3.4.2 Antibacterial activity ............................................................................................................. 31 3.4.3 Antifungal activity ................................................................................................................. 32 3.4.4 Anti-inflammatory activity .................................................................................................... 33 3.4.5 Antioxidant activity ............................................................................................................... 34 3.5 Cytotoxicity of coumarin compound against cancer cells ....................................................... 34 3.5.1 Cell line ................................................................................................................................. 34 3.5.2 Cell maintenance ................................................................................................................... 34 3.5.3 Storage of cells ...................................................................................................................... 36 3.5.4 Cell regeneration.................................................................................................................... 36 3.5.5 Cell Enumeration ................................................................................................................... 36 3.5.6 Isolation of the monocytes from the whole blood (PBMCs) ................................................ 37 3.6 Cytotoxicity assay.................................................................................................................... 38 3.6.1 Quantitative determination of apoptosis using flow cytometry ............................................. 39 3.6.1.1
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