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Linker-Based Lecithin Microemulsions As Transdermal Drug Delivery Systems

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Linker-Based Lecithin Microemulsions As Transdermal Drug Delivery Systems LINKER-BASED LECITHIN MICROEMULSIONS AS TRANSDERMAL DRUG DELIVERY SYSTEMS By Jessica Shuhong Yuan A thesis submitted in conformity with the requirements for the degree of Doctor of Philosophy Graduate Department of Chemical Engineering and Applied Chemistry University of Toronto ©Copyright by Jessica Shuhong Yuan 2009 Linker-based lecithin microemulsions as transdermal drug delivery systems Doctor of philosophy, 2009 Jessica Shuhong Yuan Department of Chemical Engineering and Applied Chemistry University of Toronto ABSTRACT The interest in microemulsions as transdermal delivery systems have been motivated by their large surface area for mass transfer, their high solubilization capacity of hydrophobic actives, and their ability to improve skin penetration. Lecithins (mixtures of phospholipids similar to those find in the skin) have been proposed as ideal surfactants in microemulsions due to their skin compatibility. Unfortunately, their incorporation into microemulsions used to require toxic medium-chain alcohols or viscous polymeric co-surfactants. Recently, microemulsion-base “green solvents” were formulated with lecithin and linker molecules. The main objective of this dissertation was to test this concept of linker-based lecithin microemulsions in transdermal delivery. In the first part of this study, linker-based lecithin formulations were developed using soybean lecithin as main surfactant, sorbitol monooleate as lipophilic linker, and caprylic acid/sodium caprylate as hydrophilic linkers. These additives, at the suggested concentration, are safe for cosmetic and pharmaceutical applications. The low toxicity of these formulations was confirmed in cultured human skin tissues. The solubilization and permeation of a common anaesthetic, lidocaine, was evaluated. The concept of “skin” permeability was introduced to account for the differences in solvent-skin partition when comparing different delivery systems. The linker- ii based lecithin microemulsion produced a substantial absorption of lidocaine into the skin, when compared to a conventional pentanol-lecithin microemulsion. The second part of this study takes advantage of the lidocaine adsorbed in the skin with the linker-based lecithin microemulsion as reservoir for in situ skin patches. The in situ patches were able to release 90% of the lidocaine over 24 hours, which is comparable to the release profile obtained from conventional polymer or gel-based patches. In the third part of this work, the role of surfactant droplets on the transport of lidocaine was studied. A mass balance model that accounted for mass transfer and partition coefficients was introduced. The parameters generated from the model confirm that in most cases the transport through the skin limits the overall penetration of lidocaine. Besides the conventional diffusion mechanism, the results suggest that surfactant droplets, carrying lidocaine, also penetrate into the skin and contribute to the accumulation of the lidocaine in the skin. iii ACKNOWLEDGEMENTS I would like to express my sincere gratitude to: • Professor. Edgar J. Acosta, my supervisor, for his intellectual guidance, endless support, and constant encouragement as an incredible driving force throughout the entire course of this project. I have been amazingly fortunate to have an advisor who gave me the freedom to explore on my own, and at the same time the guidance to recover when my steps faltered. • Professor Levente L. Diosady, Professor Ping Lee, Professor Christine Allen and Professor Pu Chen (University of Waterloo), my committee members, for their advice, insightful comments, and constructive criticisms at different stages of the research. I am grateful to them for holding me to a high research standard and enforcing strict validations for each research result. • Professor X. Y. Wen from Department of Medicine, for his guidance in fluorescence microscopy technology and kindness to share the facility. • The Government of Ontario for Ontario Graduate Scholarship (OGS) 2008-2009, the Government of Ontario/DuPont Canada Scholarship in Science and Technology (OGSST) 2007-2008, and the Government of Ontario/McLean Foundation Graduate Scholarship in Science and Technology (OGSST) 2006-2007 for the financial support in pursuing this degree. • The Innovations group at University of Toronto, especially Mr. Ian Stewart, for assisting in the applications of a patent and Ontario Research and Commercialization Program grant from the Canada Foundation for Innovation, which contributes to the economical support of this work. • The Society of Cosmetics Chemists (SCC) Ontario Chapter, especially Dr. Dennis Zuccolin, for providing me the opportunities to discuss this work with people in the cosmeceutical industry. • My fellow researchers in the Laboratory of Colloid and Formulation Engineering (LCFE): Floryunuen Garcia Becerra, Gelareh Bankian-Tabrizi, Sumit Kiran, Arti Bhakta, Nga Phuong Nguyen, Carol Xuan, Jacquelene Phia Chu, Alice Yip, Chong Liang, Micheline Samaan, Maham Ansari, and Suniya Quraishi for their discussion, friendship and smiles. • The staff of Chemical Engineering and Applied Chemistry Department with all administrative of this work. • My husband, Ted Liao, for his support, encouragement, concern and unwavering love within the past four years; my parents, especially my farther Mr. Famao Yuan, for their faith in me and allowing me to be as ambitious as I wanted; My kids, Sonya and Tim, who have taught me to enjoy life outside the lab. iv TABLE OF CONTENTS ABSTRACT................................................................................................................................... ii ACKNOWLEDGEMENTS ........................................................................................................ iv TABLE OF CONTENTS ............................................................................................................. v LIST OF FIGURES ..................................................................................................................... ix LIST OF TABLES .....................................................................................................................xiii CHAPTER 1 OVERVIEW .....................................................................................................- 1 - 1.1 OVERVIEW.......................................................................................................................- 2 - 1.2 HYPOTHESIS ...................................................................................................................- 5 - 1.3 SPECIFIC OBJECTIVES..................................................................................................- 5 - 1.4 THESIS OUTLINE............................................................................................................- 6 - 1.5 INDUSTRIAL SIGNIFICANCE ........................................................................................- 7 - 1.6 REFERENCES ..................................................................................................................- 8 - CHAPTER 2 BACKGROUND.............................................................................................- 10 - 2.1 TRANSDERMAL DRUG DELIVERY .............................................................................- 11 - 2.1.1 The skin barrier........................................................................................................- 12 - 2.1.2 Routes of skin penetration .......................................................................................- 13 - 2.1.3 Drugs........................................................................................................................- 14 - 2.1.4 Formulation approaches...........................................................................................- 15 - 2.2 MICROEMULSIONS ......................................................................................................- 16 - 2.2.1 Structures .................................................................................................................- 17 - 2.2.2 Formation.................................................................................................................- 18 - 2.2.3 Dynamic behaviour..................................................................................................- 19 - 2.2.4 Advantages and disadvantages ................................................................................- 20 - 2.2.5 Formulation constraints ...........................................................................................- 22 - 2.2.6 Lecithin microemulsions..........................................................................................- 24 - 2.3 LINKER MOLECULES IN MICROEMULSIONS ..........................................................- 28 - 2.3.1 Lipophilic linker.......................................................................................................- 28 - 2.3.2 Hydrophilic linker....................................................................................................- 29 - v 2.3.3 Self-assembly between hydrophilic and lipophilic linkers ......................................- 30 - 2.3.4 Difference with other additives................................................................................- 31 - 2.3.5 Linker-based lecithin microemulsions.....................................................................- 33 - 2.4 CONCLUSIONS..............................................................................................................-
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