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Developing Microcomposite Pharmaceutical Materials Using DEVELOPING MICROCOMPOSITE PHARMACEUTICAL MATERIALS USING DENSE GAS TECHNIQUE by KE WU A Dissertation submitted to the Graduate School-New Brunswick Rutgers, The State University of New Jersey in partial fulfillment of the requirements for the degree of Doctor of Philosophy Graduate Program in Chemistry and Chemical Biology written under the direction of Professor Jing Li and approved by ________________________ ________________________ ________________________ ________________________ New Brunswick, New Jersey October, 2008 ©2008 Ke Wu ALL RIGHTS RESERVED ABSTRACT OF THE DISSERTATION Developing Microcomposite Pharmaceutical Materials Using Dense Gas Technique By KE WU Dissertation Director: Professor Jing Li Micronized particulate pharmaceutical materials prepared using dense gas antisolvent precipitation is of great advantage over traditional micronization techniques in terms of particle size distribution and reproducibility. Our work shows that spherical particles with different degrees of agglomeration can be produced under mild operating conditions. These results stimulate further studies on the structure- property relationship of the precipitates. Preliminarily, we performed dense gas antisolvent precipitation on a number of polymers of pharmaceutical interest, including poly(DTE carbonate) and polyvinylpyrrolidone (PVP) with different molecular weights. We explored the effect of experimental conditions on the particle size and morphology. For poly (desamino tyrosyl-tyrosine alkyl ester carbonate) [poly(DTE carbonate)], its microparticles with controlled size could be applied in the field of tissue engineering, which could facilitate better exertion of the biochemical functions of this biodegradable polymer. On the other hand, PVPs are common excipients widely used in pharmaceutical formulation development. Physicochemical properties of both types of polymers ii provide flexibility of their application. Their precipitation by dense gas as antisolvent provided informative data for subsequent experiment of forming solid dispersions. Solid dispersions were prepared by precipitation of PVP with several pharmaceutical compounds using dense gas carbon dioxide as antisolvent. We focused on the morphology and particle size control of the products for the first two model drugs, prednisolone and its acetate salt, and then we prepared solid dispersions of a nonsteroidal anti-inflammatory drug, piroxicam. Microcrystals or microspheres were formed where the drug was amorphously dispersed in the polymeric matrix, with drug loadings dependent on initial drug-polymer weight ratios. The existence of interaction between the drug and polymer was confirmed through characterization of their physicochemical properties. The dissolution profiles of solid dispersions showed significant improvement in the dissolution rate of piroxicam compared with their corresponding physical mixtures and plain drug. These results manifest the great potential of this dense gas technique in improving bioavailability of water-insoluble pharmaceutical substances. iii ACKNOWLEDGEMENT I would like to express my sincere gratitude to Prof. Jing Li for accepting me as a Ph.D. student in her group, and for her continuous guidance, advice, and support during the course of my research. I am sincerely grateful to my committee members, Dr. Gene Hall, Dr. Ralf Warmuth, and Dr. Wayne Wang for serving on my thesis committee with their expertise of science. I'm also grateful to Dr. Laurence Romsted, who served as a member of my proposal defense committee two years ago. I am grateful to Dr. David Olson for his help during the course of my study. His assistance in building apparatus and in my daily experiments has significantly improved my work skill and I have learned a great deal from him about mechanical and engineering concepts. I would like to thank Dr. Joachim Kohn for providing poly(DTE carbonate) samples for part of this study. Many thanks to Mr. Valentin Starovoytov at the Department of Cell Biology and Neuroscience for his continuous assistance in providing access to the SEM facilities. I am also thankful to the staffs at the machine shop in the Department of Physics and Astronomy, whose expertise was very helpful in facilitating the maintenance of our apparatus. I am very grateful to Dr. Denita Winstead for allowing me to carry out part of my thesis work at the research facilities of Johnson and Johnson Pharm. Res. and Development, L.L.C. at Raritan, NJ. I also want to express my special thanks to the scientists there with whom I had interacted. Many thanks to all former and current group members who made my time at Dr. Li’s group such a great experience. iv I am deeply grateful to Prof. Jiacheng Zhong for his advice during my pursuit of Master's degree at Wuhan University. I will never forget the years I spent in his group with our group members. I would like to thank my parents, especially my mother, Ms. Derong Zhang, who has made my life and education possible throughout these past almost thirty years. Finally, I am grateful to Xiaojie Huang, my endeared wife, for her constant encouragement and support over the past years of our marriage. v TABLE OF CONTENTS ABSTRACT OF THE DISSERTATION ......................................................................ii ACKNOWLEDGEMENT ............................................................................................iv TABLE OF CONTENTS..............................................................................................vi LIST OF TABLES.........................................................................................................x LIST OF ILLUSTRATIONS........................................................................................xi LIST OF ABBREVIATOINS....................................................................................xvii LIST OF SYMBOLS ...................................................................................................xx CHAPTER 1 INTRODUCTION ...................................................................................1 1.1 Background..........................................................................................................1 1.1.1 Micronization (Particle size reduction).........................................................2 1.1.2 Composite particles.......................................................................................4 1.2 Dense Gas Technique ..........................................................................................6 1.2.1 Properties of dense gas carbon dioxide.........................................................9 1.2.2 Dense gas as solvent: Rapid Expansion of Supercritical Solutions (RESS) ..............................................................................................................................12 1.2.3 Dense gas as solute: Particles from Gas-Saturated Solutions (PGSS)........14 1.2.4 Dense gas as antisolvent .............................................................................15 1.3 Particle Design Using Dense Gas Antisolvent Technique.................................18 1.4 Fundamentals of Dense Gas Antisolvent Technique.........................................18 1.4.1 Thermodynamics.........................................................................................19 1.4.2 Mass transfer...............................................................................................20 1.4.3 Hydrodynamics...........................................................................................20 1.5 Motivation and Objective ..................................................................................21 CHAPTER 2 EXPERIMENTALS ..............................................................................24 vi 2.1 Dense Gas Antisolvent Precipitation .................................................................24 2.1.1 Experimental setup......................................................................................24 2.1.2 Experimental procedure of dense gas antisolvent precipitation .................26 2.2 Spray Drying......................................................................................................26 2.3 Preparation of Physical Mixture ........................................................................27 2.4 Morphological and Dimensional Characterization ............................................27 2.4.1 Scanning electron microscope (SEM) experiment .....................................27 2.4.2 Image analysis.............................................................................................27 2.4.3 Laser diffraction particle size analysis........................................................27 2.5 Physicochemical Characterization.....................................................................28 2.5.1 Powder x-ray diffraction (PXRD)...............................................................28 2.5.2 Fourier-transform infrared spectroscopy (FT-IR).......................................29 2.5.3 Differential scanning calorimetry (DSC)....................................................29 2.6 In Vitro Dissolution............................................................................................30 2.6.1 Assay of drug loading .................................................................................30 2.6.2 Dissolution studies......................................................................................30 2.7 Preliminary Experiments on Micronization of Polyvinylpyrrolidone (PVP)
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