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Non-Ionic Surfactant-Based Organogels: Their Structures and Potential As Vaccine Adjuvants

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Non-Ionic Surfactant-Based Organogels: Their Structures and Potential As Vaccine Adjuvants Non-ionic surfactant-based organogels: their structures and potential as vaccine adjuvants A thesis presented by Sudaxshina Murdan, BPharm in partial fulfilment of the requirements for the degree of Doctor of Philosophy of the University of London The School of Pharmacy University of London Brunswick Square December 97 London, UK ProQuest Number: 10104254 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest. ProQuest 10104254 Published by ProQuest LLC(2016). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code. Microform Edition © ProQuest LLC. ProQuest LLC 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106-1346 Abstract The research described in this thesis was undertaken to investigate firstly, the gelation of certain organic solvents by the non-ionic surfactant, sorbitan monostearate, and secondly, to investigate the immunoadjuvanticity of multi-component vesicle-in- water-in-oil (v/w/o) organic gels. Sorbitan monostearate causes the gelation of a number of organic solvents, for example hexadecane and isopropyl myristate, to produce opaque, semi-solid, thermoreversible, physical organic gels (organogels). The organogel’s microstructure is a 3-dimensional network of tubules dispersed in the organic fluid phase. Gelation of organic solvents occurs on cooling a hot (60^C) solution/suspension of the gelator. Cooling results in reduced solvent-surfactant affinities and consequent surfactant self- assembly into tubules which interact and form the 3-dimensional network. Inclusion of a second surfactant, such as the hydrophilic polysorbate 20, in hexadecane gels increases the solubility of sorbitan monostearate in the solvent, enhances gel stability and results in star-shaped cluster arrangements, presumably of the surfactant tubules. An aqueous phase, water itself or a niosome suspension containing entrapped antigens, can be added to the organogel to produce the multi-component systems, water-in-oil (w/o) and vesicle-in-water-in-oil (v/w/o) gels respectively. The aqueous phase is located within the hydrophilic surfactant tubules and consequently, aqueous electroconductive channels are established in the organic gel. A v/w/o gel entrapping antigen was investigated for its immunoadjuvant properties. In vivo clearance studies in mice showed the v/w/o gel acts as an antigenic depot at the site of injection after intramuscular injection and releases the model antigen, bovine serum albumin, over a period of days. Immunogenicity studies using the influenza virus haemagglutinin (HA) subunit as the antigen, showed that w/o and v/w/o organogels significantly enhance the primary and secondary anti-HA antibody titres compared to aqueous and niosome suspensions. However, when a lower antigen dose is used, the v/w/o gel does not show immunoadjuvant abilities. This reflects the need for a minimum antigen load per vesicle for adjuvanticity. To Mama thank you, for letting me be. ^ tefl- 3T# I ^ ’'^TTfl- wrrt I 3ft Tft 3ft ttT 3fr ïït 3ft Tft ...... Ill Why do people always expect authors to answer questions? I am an author because I want to ask questions. If I had answersy F d be a politician. Eugene Ionesco IV Acknowledgements After 3 years, this thesis is nearly ready. Three years of joy, sadness, excitement, frustrations, laughter, tears. I would like to thank a number of people who have shared this experience and made it quite enjoyable overall. My thanks to my two supervisors; to Professor Sandy Florence for his keen interest in the subject, for his enthusiasm for all things weird and wonderful and for his gentle guidance these past three years. Special thanks for taking the thesis manuscripts on his numerous trips and their prompt return. Thanks to Professor Gregory Gregoriadis, my other supervisor, for a number of extremely fruitful discussions, especially during the writing up phase, for the helpful tips and for my training during the past few years. My thanks go to a number of people who have helped with the experimental and technical side; to Professor Roy Jennings for kindly providing the heamagglutinin subunit, to Cristina Lopez-Pascual for the separation of free from entrapped haemagglutinin, to Benedicte van den Bergh for the freeze fracture experiments, to Dr Jeremy Cockcroft for the X-ray diffraction measurements, to Colin James for the molecular modelling of the surfactants, to Donna, Dave and Steve who helped me greatly during the in vivo experiments and to Dr Jee for the kind loan of his Wayne- Kerr bridge. Special thanks go to Dave McCarthy for his invaluable help with the microscopic analysis, friendship and especially the wonderful coffee. For friendship, companionship, laughter and affection, I thank Ijeoma, Ana, Fausto, Kirsten, Jean Christophe, Parinya, Sherry, Victoria, Ibrahim, Sakthi, Marie Sophie, Charlotte, Dejana and Brenda. Thank you guys for making the lab a very lively place. My thanks also go to Barbara, the Italian Bella, to the mulberry pickers, Bruce, Jack and Shahnaz and to Karol for some very enjoyable teas, hikes, shivery autumnal barbecues, and especially the pictionary games. To Juanita and Barathi, thank you for bearing with me all these years, for listening and being there, at the other end of the phone line. To Marcus, thank you Chéri, for everything. To Mama, Yash, Bhay, Ajay, Mounou, thank you Darlings, for your support, prayers and love. Final word to my late Father for his vision, ambition and belief in me. Table of contents Abstract ........................................................................................................ » Abbreviations ...................................................................................... xvm Thesis Aims and Rationale ............................................................1 Aims.................................................................................................................. 1 Background and rationale ..................................................................................2 I) Gelation of organic solvents by sorbitan monostearate......................................................2 II) Vesicle-in-water-in-oil gel: vaccine adjuvant .....................................................................3 Thesis structure.................................................................................................. 6 Chapter 1: Literature review ........................................................ 7 1.1 Organic gels (organogels) .........................................................................7 LI. I Gel formation...................................................................................................................... 10 Preparation .............................................................................................................................. 10 Sol to gel transition and gelation temperature (Tg) ............................................................... 11 1.1.2 Gel network........................................................................................................................15 v i Self-assembly of gelator molecules into aggregates .............................................................. 15 Formation of a 3-dimensional network ..................................................................................18 1.1.3 Role of the liquid medium in the gel................................................................................21 Solubilising power ..................................................................................................................22 Polarity ....................................................................................................................................22 Molecular shape of solvent molecule .................................................................................... 23 Functional group .....................................................................................................................24 1.1.4 Potential applications of organogels ..............................................................................26 Biotransformation using enzymes solubilised in MBGs and lecithin gels...........................27 Other syntheses.......................................................................................................................28 Transdermal drug delivery ..................................................................................................... 28 Other potential applications ................................................................................................... 29 1.1.5 Vesicle-in-water-in-oil (vlwlo) gel as a potential vaccine adjuvant .........................31 1.2 Adjuvants ........................................................................................................................... 32 1.2.1 Effects of adjuvants............................................................................................................33 1.2.2 Mode of action of adjuvants............................................................................................ 34 1.2.3 Considerations in the choice of adjuvants.....................................................................
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