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First Line of Title COLLAGEN LIKE PEPTIDE BIOCONJUGATES FOR TARGETED DRUG DELIVERY APPLICATIONS by Tianzhi Luo A dissertation submitted to the Faculty of the University of Delaware in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Materials Science and Engineering Fall 2016 © 2016 Tianzhi Luo All Rights Reserved ProQuest Number:10243851 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. ProQuest 10243851 Published by ProQuest LLC ( 2017). 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, MI 48106 - 1346 COLLAGEN LIKE PEPTIDE BIOCONJUGATES FOR TARGETED DRUG DELIVERY APPLICATIONS by Tianzhi Luo Approved: __________________________________________________________ Darrin J. Pochan, Ph.D. Chair of the Department of Materials Science and Engineering Approved: __________________________________________________________ Babatunde A. Ogunnaike, Ph.D. Dean of the College of Engineering Approved: __________________________________________________________ Ann L. Ardis, Ph.D. Senior Vice Provost for Graduate and Professional Education I certify that I have read this dissertation and that in my opinion it meets the academic and professional standard required by the University as a dissertation for the degree of Doctor of Philosophy. Signed: __________________________________________________________ Kristi L. Kiick, Ph.D. Professor in charge of dissertation I certify that I have read this dissertation and that in my opinion it meets the academic and professional standard required by the University as a dissertation for the degree of Doctor of Philosophy. Signed: __________________________________________________________ Darrin J. Pochan, Ph.D. Member of dissertation committee I certify that I have read this dissertation and that in my opinion it meets the academic and professional standard required by the University as a dissertation for the degree of Doctor of Philosophy. Signed: __________________________________________________________ Xinqiao Jia, Ph.D. Member of dissertation committee I certify that I have read this dissertation and that in my opinion it meets the academic and professional standard required by the University as a dissertation for the degree of Doctor of Philosophy. Signed: __________________________________________________________ Millicent O. Sullivan, Ph.D. Member of dissertation committee ACKNOWLEDGMENTS I am heartily thankful to all the people who supported and encouraged me and kept my spirits high during my years of the PhD. This work would not have been so exciting for me without their help. It is my honor to acknowledge them in this section. I am very grateful to my advisor Professor Kristi L. Kiick for her excellent scientific guidance and critical discussions. I also had a great learning from her fantastic teaching skills as the instructor of several courses. Her enthusiasm and encouragement for new and exciting scientific works kept me motivated towards the commitments of my thesis work. The aptitudes acquired by me while working under her guidance has constantly shaped me in becoming a better scholar. I am deeply grateful to Professor Kiick for all her efforts to promote me as an independent scientist. I am very grateful to my committee members, Professor Xinqiao Jia, Professor Millicent O. Sullivan, and Professor Darrin J. Pochan for their profound scientific advice and providing research facility for carrying out various works described in this thesis. I am deeply grateful to them for their flexible schedule and technical discussions with me that helped me sort out the technical details of my work. I sincerely thank Professor Patrick Theato and Ronghe Li, at the University of Hamburg, Germany, for our excellent collaborative work on diblock collagen peptide polymer conjugate. I sincerely thank all my past lab members (Dr. Shuang Liu, Dr. Aaron Baldwin, Dr. Sarah Grieshaber, Dr. Linqing Li, Dr. Eric Levenson, Dr. Christopher McGann, Dr. Nandita Bhagwat, Ingrid Spielman, Bo Xie, Dr. Prathamesh Kharkar, Dr. Yingkai iv Liang, Dr. Samuel Lahasky, Dr. Kenneth Koehler, Dr. Shivshankar Mane) and present lab members (Dr. Rebecca Scott, Bradford Paik, Morgan Urello, Hang Kuen Lau, Michael Haider, Yu Tian, Haocheng Wu, Danielle Ferguson, Lucas Dunshee, Ming Fan) for technical and scientific discussions. Their company made my life easier on multiple occasions. I am thankful to Rachel Letteri at University of Massachusetts for help on organic phase GPC and Dr. Chaoying Ni, Frank Kriss, Fei Deng and Jennifer Sloppy for help on TEM and cryo-TEM. I am also thankful to the efforts and support of all staffs (especially Robin Buccos, Kathy Forwood, Laura Mohr, Dionne Putney, Christine Williamson, and Charlie Garbini) of the department of Material Science and Engineering. I would like to thank all my friends for their advice and support. They helped me make this thesis work possible and make my life easier here at UD. I especially thank Linqing Li, Bo Xie, Jun Jiang, Fan Xu, Xiaoshan Xu, Ying Hao, Hang Kuen Lau, Shuyu Xu, Eric Fowler, Nandita Bhagwat, Xiaowei Yang, Xinyi Wang, Xiaocao Hu and Bradford Paik for their great company and fun time. I dedicate this work to my mother Xiaoping Yan who brought me to the world, my father Fei Luo who taught me the rules, and my advisor Kristi Kiick who guided me into the world of science. v TABLE OF CONTENTS LIST OF TABLES ......................................................................................................... x LIST OF FIGURES ....................................................................................................... xi ABSTRACT ................................................................................................................. xx Chapter 1 BACKGROUND ................................................................................................ 1 1.1 Introduction ............................................................................................... 1 1.2 Triple Helix Stability ................................................................................. 3 1.2.1 Role of (4R)-hydroxyproline ......................................................... 4 1.2.2 Electrostatic interactions ............................................................... 6 1.2.3 Cystine knots ................................................................................. 8 1.2.4 Template stabilization ................................................................... 9 1.3 Higher Order Assembly ........................................................................... 11 1.3.1 π-π stacking interaction ............................................................... 12 1.3.2 Lateral electrostatic interactions .................................................. 13 1.3.3 Metal-triggered assembly ............................................................ 15 1.4 Triple Helix Hybridization ...................................................................... 18 1.5 Synthetic Polymer – CLP Bioconjugates ................................................ 21 1.5.1 Assembly of polymer–CLP conjugates ....................................... 22 1.5.2 Collagen/CLP containing hydrogels ............................................ 24 1.6 Conclusions ............................................................................................. 27 1.7 Acknowledgements ................................................................................. 28 REFERENCES ................................................................................................. 29 2 THERMORESPONSIVE SELF-ASSEMBLY OF NANOSTRUCTURES FROM A COLLAGEN-LIKE PEPTIDE-CONTAINING DIBLOCK COPOLYMER ................................................................................................. 41 vi 2.1 Introduction ............................................................................................. 41 2.2 Experimental Section ............................................................................... 45 2.2.1 Materials ...................................................................................... 45 2.2.2 Peptide Synthesis ......................................................................... 45 2.2.3 PDEGMEMA-CLP Conjugate Synthesis .................................... 46 2.2.4 Nuclear Magnetic Resonance (NMR) ......................................... 47 2.2.5 Gel Permeation Chromatography (GPC) ..................................... 47 2.2.6 Circular Dichroic Spectroscopy (CD) ......................................... 48 2.2.7 Dynamic Light Scattering (DLS) ................................................ 49 2.2.8 Transmission Electron Microscopy (TEM) ................................. 49 2.3 Results and Discussion ............................................................................ 50 2.3.1 Synthesis of PDEGMEMA-CLP Diblock Polymer .................... 50 2.3.2 Triple Helix Formation ................................................................ 54 2.3.3 Temperature Triggered Self-Assembly into Nanoparticles ......... 59 2.4 Conclusions ............................................................................................
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