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Synthesis and Characterization of Antioxidant Conjugated Poly(Βeta-Amino Ester) Micro/Nanogels for the Suppression of Oxidative Stress

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Synthesis and Characterization of Antioxidant Conjugated Poly(Βeta-Amino Ester) Micro/Nanogels for the Suppression of Oxidative Stress University of Kentucky UKnowledge Theses and Dissertations--Chemical and Materials Engineering Chemical and Materials Engineering 2016 SYNTHESIS AND CHARACTERIZATION OF ANTIOXIDANT CONJUGATED POLY(ΒETA-AMINO ESTER) MICRO/NANOGELS FOR THE SUPPRESSION OF OXIDATIVE STRESS Prachi Gupta University of Kentucky, [email protected] Digital Object Identifier: http://dx.doi.org/10.13023/ETD.2016.035 Right click to open a feedback form in a new tab to let us know how this document benefits ou.y Recommended Citation Gupta, Prachi, "SYNTHESIS AND CHARACTERIZATION OF ANTIOXIDANT CONJUGATED POLY(ΒETA- AMINO ESTER) MICRO/NANOGELS FOR THE SUPPRESSION OF OXIDATIVE STRESS" (2016). Theses and Dissertations--Chemical and Materials Engineering. 58. https://uknowledge.uky.edu/cme_etds/58 This Doctoral Dissertation is brought to you for free and open access by the Chemical and Materials Engineering at UKnowledge. It has been accepted for inclusion in Theses and Dissertations--Chemical and Materials Engineering by an authorized administrator of UKnowledge. For more information, please contact [email protected]. STUDENT AGREEMENT: I represent that my thesis or dissertation and abstract are my original work. Proper attribution has been given to all outside sources. I understand that I am solely responsible for obtaining any needed copyright permissions. I have obtained needed written permission statement(s) from the owner(s) of each third-party copyrighted matter to be included in my work, allowing electronic distribution (if such use is not permitted by the fair use doctrine) which will be submitted to UKnowledge as Additional File. I hereby grant to The University of Kentucky and its agents the irrevocable, non-exclusive, and royalty-free license to archive and make accessible my work in whole or in part in all forms of media, now or hereafter known. I agree that the document mentioned above may be made available immediately for worldwide access unless an embargo applies. I retain all other ownership rights to the copyright of my work. I also retain the right to use in future works (such as articles or books) all or part of my work. I understand that I am free to register the copyright to my work. REVIEW, APPROVAL AND ACCEPTANCE The document mentioned above has been reviewed and accepted by the student’s advisor, on behalf of the advisory committee, and by the Director of Graduate Studies (DGS), on behalf of the program; we verify that this is the final, approved version of the student’s thesis including all changes required by the advisory committee. The undersigned agree to abide by the statements above. Prachi Gupta, Student Dr. Thomas D. Dziubla, Major Professor Dr. Thomas D. Dziubla, Director of Graduate Studies SYNTHESIS AND CHARACTERIZATION OF ANTIOXIDANT CONJUGATED POLY(ΒETA-AMINO ESTER) MICRO/NANOGELS FOR THE SUPPRESSION OF OXIDATIVE STRESS DISSERTATION A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the College of Engineering at the University of Kentucky By Prachi Gupta Lexington, Kentucky Director: Dr. Thomas Dziubla, Associate Professor of Chemical and Materials Engineering Co-director: Dr. J. Zach Hilt, Professor of Chemical and Materials Engineering Lexington, Kentucky Copyright © Prachi Gupta 2016 ABSTRACT FOR DISSERTATION SYNTHESIS AND CHARACTERIZATION OF ANTIOXIDANT CONJUGATED POLY(ΒETA-AMINO ESTER) MICRO/NANOGELS FOR THE SUPPRESSION OF OXIDATIVE STRESS Oxidative stress is a pathophysiological condition defined by an increased production of reactive oxygen species (ROS), which can result in the growth arrest of cells followed by cell disintegration or necrosis. A number of small molecule antioxidants (e.g. curcumin, quercetin and resveratrol) are capable of directly scavenging ROS, thereby short-circuiting the self-propagating oxidative stress state. However, poor solubility and rapid 1st pass metabolism results in overall low bioavailability and acts as a barrier for its use as a drug to suppress oxidative stress efficiently. To overcome this limitation, these small molecule antioxidants were covalently conjugated into poly(β-amino ester) (PβAE) cross-linked networks to formulate prodrug gel microparticles and nanoparticles (nanogels). Being hydrolytically degradable in nature, these PβAE crosslinked systems released antioxidants in their original structural form in a sustained controlled fashion. Both quercetin and curcumin-PβAE nanogels showed prolonged suppression of cellular oxidative stress induced by H2O2. Curcumin PβAE nanogels also demonstrated protection against mitochondrial oxidative stress induced by H2O2 and polychlorinated biphenyls. Curcumin-PβAE gel microparticles were also developed as a platform to treat oral mucositis through a local antioxidant delivery route. The same synthesis chemistry was transferred to formulate resveratrol PβAE gel microparticles for topical applications, to treat UV radiation induced oxidative stress. Both formulations showed suppression of induced oxidative stress. An in vivo trial with curcumin-PβAE microparticles further showed relatively reduced the severity of induced oral mucositis (OM) in hamster check pouch as compared to placebo. Keywords: Poly(β amino esters), antioxidants, oxidative stress, nanogels, microparticles Prachi Gupta 3/11/16 SYNTHESIS AND CHARACTERIZATION OF ANTIOXIDANT CONJUGATED POLY(ΒETA-AMINO ESTER) MICRO/NANOGELS FOR THE SUPPRESSION OF OXIDATIVE STRESS By Prachi Gupta Dr. Thomas Dziubla (Director of Dissertation) Dr. J. Zach Hilt (Co-director of Dissertation) Dr. Thomas Dziubla (Director of Graduate Studies) 3/17/16 (Date) ACKNOWLEDGEMENT This dissertation is coming to its existence as a result of positive forces that have always surrounded me; motivating parents, encouraging mentors, supportive friends and continuous blessings from an unseen force we call God. I am sincerely grateful to Dr. Thomas Dziubla, who has been my advisor, a counselor, and a boss, who constantly kept my doctoral journey interesting and challenging. Accompanying him, I would like to thank Dr. J. Zach Hilt, my co-advisor who has taken care of me and my research track with great effort and spirit. I would like to thank both of them for instilling in me the skills of an independent and innovative researcher with a very positive attitude that no result is negative. This theory surely applies in every phase of our day to day life and has transformed me into a better person over the past years. I would like to convey my gratitude to my committee members, Dr. Stephen Rankin and Dr. Bernard Hennig for giving resourceful insights into my research. I would like to further acknowledge Dr. Robert Yokel, my external examiner for taking his time to look into my dissertation and pass on valuable suggestions. I would like to thank all my research companions Paritosh, Dave, Sundar, Andrew, Nihar, Vinod, Mark, Irfan and Carolyn for maintaining a versatile, healthy and supportive work environment with a great team spirit. I also thank my undergraduate researchers, Erin, Manali, Donavyn, Caroline and John whom I got the opportunity to mentor in their research, giving me a wonderful experience throughout. iii I am blessed with great friends, and I would like to acknowledge them for their love, support and memorable time gifted to me. I am grateful to have immense support from Sakshi (Chinki), Abhinav, Rishali, Chetna, Ashwini, Bhakti, Maulik, Mitesh, Prathemesh, Manali and Hersh for countless years. My special acknowledgement goes to people who became my extended family away from home (popularly known as gazette janta) consisting of Shristi, Sonam, Suvid, Rutooj, Saket, Anwesha, Pratik Sogani, Amit, Suraj, Ishan, Ashish,, Abhishek, Priyesh, Shreya Patel, Raghav, Sumesh, Abhijit, Mini, Russel, Ravinder, and Pratik Rane. Thanks for making each and every day full of fun, adventure and innovation in this beautiful town, Lexington. I would like to acknowledge the blessings of my parents (Mrs. Manju Gupta and Prof. T. C. Gupta), and dedicate my dissertation to them. This achievement came to fruition due to their support and never ending patience. Their encouraging attitude to explore with creative freedom meanwhile instilling values into me, kept me inclined towards science from childhood. I am also grateful to my brother (Sudhanshu) and sister-in-law (Liza), who always made sure that I cross all the hurdles with confidence and guided me with practical advice during challenging times. iv TABLE OF CONTENTS ACKNOWLEDGEMENT ........................................................................................... iii LIST OF TABLES ......................................................................................................... x LIST OF FIGURES ...................................................................................................... xi 1. INTRODUCTION ................................................................................................... 1 2 BACKGROUND: A FREE RADICAL PRIMER .................................................. 7 2.1 Free radical biology – importance ................................................................... 7 2.2 RED/Ox Chemistry ....................................................................................... 10 2.2.1 Oxidation/reduction reactions and voltage potentials ............................ 10 2.2.2 Thermodynamic treatment (Ellingham diagram)................................... 15 2.2.3 Combustion sequences and/or metal oxides .........................................
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