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Solid-Phase Extraction Is Discussed

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Solid-Phase Extraction Is Discussed Sample Preparation and Biopharmaceutical Analysis by Gillian Petra Me Mahon BSc. C.Chem A Thesis submitted to D ublin City UNIVERSITY OUscoil Chathair Bhaile Atha Cliath on research carried out in conjunction with The Royal College of Surgeons in Ireland for the Degree of Doctor of Philosophy April 1998 Supervised by Dr. Mary Kelly and Prof. Richard O’Kennedy DECLARATION I hereby certify that this material, which I now submit for assessment on the programme of study leading to the award of Doctor of Philosophy (PhD) is entirely my own work and has not been taken from the work of others save and to the extent that such work has been cited and acknowledged within the text of my work. Signed: M e Date: ID No. 94970599 Sample Preparation and Biopharmaceutical Analysis Gillian P. Me Mahon ABSTRACT In chapter 1, an overview is given of sample preparation methods and analytical techniques in use today. Each one is discussed, and relevant examples are given. In chapter 2, the development of a method for the HPLC analysis of taurine in human plasma using acetonitrile precipitation and pre-column derivatisation with fluorescamine is presented. This procedure was found to be faster and easier to use than previous taurine assays. In chapter 3, the evaluation of novel aspirin derivatives as prodrugs for transdermal aspirin delivery was made possible by an analytical procedure developed as part of this PhD. Following in vitro application of the derivative to skin, the perfusate samples in PBS could be taken and injected directly onto the HPLC system. In addition to quantifying aspirin (ASA) and its metabolite salicylic acid (SAL), the introduction of a gradient after ASA and SAL had eluted allowed determination of the parent compounds. In chapter 4, the quantitation of ASA and SAL in human plasma using column-switching HPLC with on-line solid-phase extraction is discussed. Following a simple dilution step, the plasma was injected directly onto the system. On switching the 10-port valve, the sample containing the extracted ASA and SAL was sent to the analytical column for quantitation. The protocol was successfully applied to the investigation of levels of these compounds in healthy volunteers following an oral dose of aspirin. In chapter 5, identification and qualitative analysis of a cachectic factor and its albumin- bound complex in the urine of cancer patients with cachexia is presented. This work was carried out using capillary electrophoresis. ACKNOWLEDGEMENTS Firstly, I would like to thank my supervisor in The Royal College of Surgeons, Dr. Mary Kelly, for her support throughout the course of this research and during the preparation of this thesis. I also wish to express my appreciation to Prof. Kevin Nolan for his encouragement of my work. A special word of thanks goes to Terry Murphy for his help in setting up and maintaining the ‘basement lab’, without which this research could never have been done. Thanks to the other postgraduate students who have worked alongside me over the years and become my friends - Eimear, Julie, Karen, Orla, Joe and Tony. They have been through the best and worst times with me and always manage to make me laugh. I would also like to acknowledge the other staff members of the Chemistry and Physics Departments who are a pleasure to work with. I am very grateful to Celine (my ofFice- mate) for her help, advice and patience over the last few hectic weeks of thesis-writing. Thanks to Kevin McGuigan for the use of his computer in the evenings, without which I would have been lost. A special thank-you goes to Bairbre in Media Services for her assistance with my thesis. I am very grateful to Prof. Richard O’Kennedy for being a mentor to me, not only during the past three years of this PhD, but throughout my third level education. He has been a great source of optimism and reassurance. He is someone for whom I have a great deal of admiration and whose abilities continue to inspire me. To some personal friends Dec R, Dec B, Donagh, Aido, Frank, Emo and Dee for the weekends away, holidays (sun and ski) and the many occasions involving alcohol. To the ‘Castleknock Crowd’ - Weezie, Orlaith, Mary and Sheena who are very dear to me and have encouraged me throughout these PhD years. Thank you to Carol who has been there and supported me (in all things) for twenty years and told me it would be worth it in the end. I also want to thank the ‘girlies’ who went through college with me - Sinead, Tess, Joby and Gillian - for all the good times. And finally, to my family without whom I would never have begun this journey. I am indebted to my parents who have given me absolutely everything a daughter could want - I love you both very much. Thank you for educating and encouraging me throughout my life. Thanks for listening to me, for your words of advice, and most of all, for being there for me when I needed you. A special appreciation goes to my sisters and my brother. Jennifer and Hilary, you are the best sisters in the world and 1 cherish you both. Graham, thanks for being a voice of reason and a wonderful brother to me. For Alan I love you very much Thanks for everything “It is a great thing to make scientific discoveries of rare value, but it is even greater to be willing to share these discoveries and to encourage other workers in the same field of scientific research. ” William J. Mayo, 1935 Chapter 1 : Introduction to Sample Preparation and Biopharmaceutical Analysis 1.1 SAMPLE PREPARATION IN BIOPHARMACEUTICAL ANALYSIS .....................2 1.1.1 C O L L E C T IO N O F B IO S A M P L E S .................................................................................2 1.1.2 STORAGE OF BIOSAMPLES .......................................................................................... 4 1.1.3 TRANSPORT OF BIOSAMPLES .................................................................................... 4 1.1.4 PRETREATMENT OF BIOSAMPLES .........................................................................5 1.1.4.1 Protein Precipitation.................................................................................................................6 1.1.4.2 Liquid Extraction Techniques................................................................................................. 7 1.1.4.3 Solid-Phase Extraction Techniques.......................................................................................12 1.1.4.4 Membrane Techniques...........................................................................................................19 1.2 ANALYTICAL TECHNIQUES IN BIOPHARMACEUTICAL ANALYSIS 22 1.2.1 IMMUNOASSAY .................................................................................................................. 22 1.2.1.1 Radioimmunoassay................................................................................................................. 24 1.2.1.2 Enzyme Immunoassay............................................................................................................26 1.2.1.3 Fluorescence Immunoassays................................................................................................. 27 1.2.1.4 Chemiluminescence Immunoassays.....................................................................................28 1.2.1.5 Molecular Imprinting Assays................................................................................................ 28 1.2.2 SPECTROMETRY ...............................................................................................................28 1.2.2.1 UV-Vis and Fluorescence Spectrometry..............................................................................29 1.2.2.2 Infrared Spectrometry.............................................................................................................31 1.2.2.3 Nuclear Magnetic Resonance Spectrometry.........................................................................32 1.2.2.4 Mass Spectrometry.................................................................................... 32 1.2.3 ELECTROCHEMISTRY ...................................................................................................33 1.2.3.1 Potentiometry.......................................................................................................................... 33 1.2.3.2 Voltammetiy/Polarography................................................................................................. 34 1.2.4 CHROMATOGRAPHY ...................................................................................................... 36 1.2.4.1 Principles of Chromatography................................ .......... 36 1.2.4.1.1 History of Chromatography............................................................................................37 1.2.4.1.2 Theory of Chromatography.............................................................................................37 1.2.4.1.3 Retention Mechanisms in Chromatography..................................................................41 1.2.4.1.4 Identification and Quantitation in Chromatography................... 43 1.2.4.2 Thin Layer Chromatography................................................................................................ 44 1.2.4.2.1 Detection in T L C ............ 46 1.2 4.2.2 Identification and Quantitation in T L C ..................... 46 1.2.4.3 Gas Chromatography.............................................................................................................46 1.2.4.3.1 Columns in G C .............................................................................................................
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