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Surfactants, Polyelectrolytes and Nanoparticles As Building Blocks for Nanocarriers

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Surfactants, Polyelectrolytes and Nanoparticles As Building Blocks for Nanocarriers The Jerzy Haber Institute of Catalysis and Surface Chemistry Polish Academy of Sciences SURFACTANTS, POLYELECTROLYTES AND NANOPARTICLES AS BUILDING BLOCKS FOR NANOCARRIERS Małgorzata Adamczak PhD Thesis Supervised by Professor Piotr Warszyński Kraków, 2013 Acknowledgments First, I would like to thank my supervisor Professor Piotr Warszyński for mentoring me during this project. I am very grateful for giving me room to grow and come up with my own ideas, as well as allowing me to learn on my mistakes, while he was always there with valuable suggestions when needed. I would also like to express my gratitude to Dr. Christian Simon from Sintef Materials and Chemistry, who was our foreign partner in the project. Off and on, I’ve spent twenty months in Oslo, Norway, which eventually became my second home. My special thanks go to Christelle Denonville, Bente Gilbu Tilset, Isabelle Marthinsen, Marit Stange, Juan Yang, Henrik Raeder, Mathieu Grandcolas and Per Martin Rorvik. Tusen takk til alle sammen! I would like to acknowledge two amazing teams, which performed the biological tests of my capsules: Hanna Julie Hoel and Professor Gustav Gaudernack from Institute for Can- cer Research at the Norwegian Radium Hospital in Oslo, Norway, and Dr. hab. Elżbieta Pamuła, Małgorzata Krok and Urszula Posadowska from Faculty of Materials Science and Ceramics, AGH University of Science and Technology in Kraków, Poland. I would like to thank all the members of two groups, Colloids and Nanostructures of Soft Matter, for a friendly atmosphere in the laboratories, support and scientific discus- sions. Special acknowledgments need to be given to Dr. Grażyna Para, Dr. Ewelina Jarek, Dr. Aneta Michna, Dr. Małgorzata Nattich-Rak, Marzena Noworyta, Joanna Piekoszewska and Karolina Podgórna. It is hard to fully express gratitude to my friends, Maria Dąbkowska (Zaucha:), Monika Stefańska, Jakub Barbasz and Krzysztof Szczepanowicz, for what they have done for me during all these years. You made it all worthwhile. Thanks. I also would like to thank my partner, Carlos Grande, for his love and support, together with ability to distinguish when it was better to let me stay home writing and eating ice cream, and when it was a good time to take me for a run. You are the only exception. Most importantly, this thesis would not have been possible without my family. I would especially like to thank my parents and both brothers for their love, understanding, en- couragement and endless support. This work was supported by the “Krakow Interdisciplinary PhD-Project in Nanoscience and Advanced Nanostructures”, which is operated within the Foundation for Polish Sci- ence MPD Programme co-financed by the EU European Regional Development Fund. Contents 1 LITERATURE REVIEW 1 1 Introduction................................... 1 2 Surfactants and micelles . 3 2.1 Surfactants ............................... 3 2.1.1 General properties and classification of surfactants .... 3 2.1.2 Interfacial tension . 9 2.1.3 Adsorption of surfactants at an interface . 11 2.1.4 Thermodynamics of adsorption at interfaces . 12 2.2 Micelles ................................. 15 2.2.1 The critical micelle concentration . 15 2.2.2 Thermodynamics of micellization . 18 2.2.3 Micelle dynamics . 20 2.2.4 Structure of surfactant aggregates . 21 2.2.5 Micellar solubilization . 23 3 Emulsions .................................... 25 3.1 General properties . 25 3.2 Thermodynamics of emulsification . 26 3.3 Classification of emulsions . 27 3.4 Methods of emulsification . 28 3.4.1 High-energy techniques . 29 3.4.2 Low-energy techniques . 30 3.5 Roleofemulsifiers............................ 34 3.5.1 Steric stabilization . 35 3.5.2 Selection of a surfactant . 35 i CONTENTS 3.6 Important aspects of emulsion stability . 38 3.6.1 Van der Waals forces . 41 3.6.2 Electrostatic forces . 44 3.6.3 The Poisson-Boltzmann theory of diffuse double layer . 47 3.6.4 Electrokinetic phenomena and the zeta potential . 50 3.6.5 Total energy of interactions . 52 4 Polyelectrolytes ................................. 54 4.1 General properties . 54 4.2 Polyelectrolytes in solution . 55 4.3 Polyelectrolytes at interfaces . 57 4.4 Multilayer formation . 59 4.5 Polyelectrolyte complexes . 61 4.5.1 Polyelectrolyte complex formation with oppositely charged polyelectrolytes . 61 4.5.2 Polyelectrolyte complex formation with oppositely charged surfactants .......................... 62 4.5.3 Polyelectrolyte complex formation with nanoparticles . 64 4.6 Applications of polyelectrolytes . 65 5 Nanoparticles and nanocarriers for drug delivery . ........ 66 5.1 Drugdelivery .............................. 66 5.2 Advantages of scaling down-nanosize . 66 5.3 Application of colloidal properties in drug delivery . ........ 68 5.4 Nanoparticles for imaging applications . 70 5.4.1 Quantum dots . 70 5.4.2 Magnetic nanoparticles . 74 5.5 Nanocapsules prepared by layer-by-layer adsorption of polyelectrolytes 75 5.5.1 Introduction . 75 5.5.2 Polyelectrolyte capsules with solid core . 78 5.5.3 Polyelectrolyte capsules with liquid core . 79 5.5.4 Shell materials . 81 5.6 Nanoparticles: health and environmental risks . ..... 82 ii CONTENTS 2 EXPERIMENTAL PART 83 6 Theaimofthework .............................. 83 7 Experimentalmethods ............................. 84 7.1 Dynamic Light Scattering . 84 7.2 Electrophoretic mobility measurements . 87 7.3 Atomic Force Microscopy . 89 7.4 Fluorescence spectroscopy . 91 7.5 UV-visspectroscopy .......................... 93 7.6 Interfacial tension measurements . 94 7.7 Cytotoxicitytests............................ 95 7.7.1 Proliferation assay and test of unspecific binding . 95 7.7.2 Cell-viability test MTT . 97 7.7.3 Cell morphology observations . 98 8 Materials .................................... 98 8.1 Surfactants ............................... 98 8.2 Polyelectrolytes . 99 8.3 Oils ...................................100 8.4 Active agents for encapsulation . 101 8.5 Others..................................102 9 Experimental results and discussion . 102 9.1 Polyelectrolyte multilayer capsules with hydrophilic quantum dots . 102 9.1.1 Outline ............................102 9.1.2 Preparation of the complexes of quantum dots with poly- cations and formation of capsules by LbL adsorption . 103 9.1.3 AFM topographical images of quantum dots and nanocap- sules..............................111 9.1.4 Fluorescence spectra of encapsulated quantum dots . 112 9.1.5 Cytotoxicity test of encapsulated quantum dots . 113 9.1.6 Test of unspecific binding . 115 9.2 Natural oil cores prepared by spontaneous emulsification technique 117 9.2.1 Outline ............................117 iii CONTENTS 9.2.2 Interfacial tension measurements at vegetable oils/water interface............................117 9.2.3 The dependence of emulsion drop size and zeta potential on type of oil, oil-to-ethanol ratio and preparation technique119 9.2.4 The dependence of the emulsion particle size and zeta po- tential on the type of surfactant and its concentration . 122 9.2.5 Stability of the emulsions . 125 9.2.6 Encapsulation of emulsions within a first layer of polyelec- trolyte.............................127 9.2.7 Fluorescence of encapsulated hydrophobic dye . 129 9.3 Linseed oil based nanocapsules as delivery system for hydrophobic quantumdots ..............................130 9.3.1 Outline ............................130 9.3.2 Encapsulation of CdSe/ZnS quantum dots . 132 9.3.3 AFM measurements of nanocapsules morphology . 134 9.3.4 Fluorescence of encapsulated quantum dots . 135 9.3.5 MTT viability test . 136 9.3.6 Cell morphology observations . 138 9.4 Preparation of the squalene-based nanocapsules on membrane emul- sificationunit ..............................138 9.4.1 Outline ............................138 9.4.2 Formation of the squalene-based nanocapsules . 141 9.4.3 Elastic properties of the squalene-based capsules . 146 9.4.4 Encapsulation of model drugs in squalene based nanocap- sules..............................147 10 Conclusions ...................................149 10.1 Encapsulation of hydrophilic quantum dots within polyelectrolyte multilayers................................150 10.2 Natural oil cores prepared by spontaneous emulsification technique 150 10.3 Linseed oil based nanocapsules as delivery system for hydrophobic quantumdots ..............................151 iv CONTENTS 10.4 Preparation of squalene-based nanocapsules on membrane emulsifi- cationunit................................151 Bibliography 153 List of Symbols 169 v Chapter 1 LITERATURE REVIEW 1 Introduction Once described as “pseudosolutions” or “world of neglected dimensions”, colloids have come a long way from their use in the enhancement of solubility of substances to the minimization of toxicity and degradation of the drugs. A colloidal suspension consists of two separate phases; one phase finely dispersed in the second continuous phase. Size of dispersed particles ranges from a few to a few thousands nanometers, which gives a rise to a large interfacial area, and various phenomena dominated by surface interactions. Colloids have been in use for centuries in different areas, including additives and pigments for inks, paints, food and cosmetics. However, only last few decades have brought the enormous development in colloid science and technology, related with expanding fields of nanotechnology and nanomedicine. Size has a significant importance in drug delivery and imaging applications. Control on the cellular level can be achieved only with structures of size similar to biological
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