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SYNTHESIS and FUNCTIONALITY STUDY of NOVEL BIOMIMETIC N-GLYCAN POLYMERS KA KEUNG CHAN Bachelor of Science Appalachian State Univ

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SYNTHESIS and FUNCTIONALITY STUDY of NOVEL BIOMIMETIC N-GLYCAN POLYMERS KA KEUNG CHAN Bachelor of Science Appalachian State Univ SYNTHESIS AND FUNCTIONALITY STUDY OF NOVEL BIOMIMETIC N-GLYCAN POLYMERS KA KEUNG CHAN Bachelor of Science Appalachian State University May 2014 submitted in partial fulfillment of requirements for the degree of DOCTOR OF PHILOSOPHY IN CLINICAL AND BIOANALYTICAL CHEMISTRY at the CLEVELAND STATE UNIVERSITY May 2021 We hereby approve this dissertation for KA KEUNG CHAN Candidate for the Doctor of Philosophy in Clinical and Bioanalytical Chemistry degree for the Department of Chemistry and Cleveland State University’s College of Graduate Studies by ______________________________________________________ Xue-Long Sun, Ph.D., Dissertation Committee Chairperson Chemistry, 4/22/2021 Department & Date ____________________________________________________________ Aimin Zhou, Ph.D., Dissertation Committee Member Chemistry, 4/22/2021 Department & Date ____________________________________________________________ Bin Su, Ph.D., Dissertation Committee Member Chemistry, 4/22/2021 Department & Date ____________________________________________________________ David Anderson, Ph.D., Dissertation Committee Member Chemistry, 4/22/2021 Department & Date ____________________________________________________________ Moo-Yeal Lee, Ph.D., Dissertation Committee Member Chemical & Biomedical Engineering, 4/22/2021 Department & Date ____________________________________________________________ Aaron Severson, Ph.D., Dissertation Committee Member Biological, Geological and Environmental Sciences, 4/22/2021 Department & Date Date of Defense: 22 APRIL 2021 DEDICATION I dedicate the entirety of this degree to my family. My mother, Mrs. Yu Hung Cheung, to whom I owe the world and I unreservedly dedicate the entire of my life and achievements – thank you for everything that you have done for me. My fiancée, Ms. Mengni Xu, to whom I dedicate the rest of my life with my undying love – you deserve all of my achievements as much as I do. ACKNOWLEDGEMENT I extend my most sincere gratitude to Dr. Xue-Long Sun, my research advisor and the chairperson of my committee, for having welcomed me into his research lab. Without his perceptions, innovations and meticulosity in science, this dissertation would not have been possible. I am grateful for the plethora of opportunities and encouragements he has provided me, which undoubtably helped set me up for a promising scientific future. I express my deep appreciation to all my committee members. Dr. David Anderson for his advocation of clinical chemistry, which had inspired me to find the area of chemistry to dedicate my career in. Dr. Aimin Zhou for his support and guidance, as well as his expertise in bio-techniques and immune signaling pathways, which had guided me to find answers to many of my questions. Dr. Bin Su and Dr. Aaron Severson for their expertise in molecular biology, which had allowed me to gain a well-rounded awareness of the science behind my studies. Dr. Moo-Yeal Lee for the valuable collaborative opportunities and his expertise in miniaturized immunoassays. Additionally, I extend a sincere special thanks to Dr. Geyou Ao for the collaborative opportunities and projects related to her expertise in carbon-based nanomaterials. I thank all past and current members in Dr. Sun’s lab for their mentorship and companionship throughout my graduate research journey, and I acknowledge all faculty and staff who had provided me with excellent support and assistance in all aspects during my time at Cleveland State University. SYNTHESIS AND FUNCTIONALITY STUDY OF NOVEL BIOMIMETIC N-GLYCAN POLYMERS KA KEUNG CHAN ABSTRACT Cell surface carbohydrates, existing as glycoproteins, glycolipids, and proteoglycans, often serve as receptors to relay critical interactions and trigger crucial signaling events in many biological processes. Glycan recognition is deeply involved in immune surveillance, response and can provide abundant opportunities to discover the molecular mechanism and potential therapeutic or diagnostic approaches for various diseases. Many useful functionalities can be achieved by developing synthetic glycans to mimic natural carbohydrates. Over the recent decade, glycopolymers, polymers with pendant carbohydrates, have continued to prove usefulness in various applications across different scientific disciplines. For example, glycopolymers can be used as biomimetic glycoligands to study protein functions, modify nanomaterials, and target immune cells to yield tailored immune responses toward a desired outcome. In this dissertation, I employed cyanoxyl-mediated free radical polymerization (CMFRP) for a straightforward synthesis of chain-end functionalized N-glycan polymer-based biomimetic glycoligands with the focus on controlling the chain-end functional group, carbohydrate ligand moiety, linkage and density, then demonstrated their various achievable functionalities. With UV-photoactivatable covalent crosslinking chemistry in mind, novel aryl azide chain-end functionalized N-glycan polymers were synthesized for affinity assisted photo-labeling of proteins that are specific to the carbohydrate moieties expressed on the polymer backbone. The synthestic glycopolymers have demonstrated promising v capabilities for specifically labeling proteins and will be useful multivalent ligands for identifying protein targets and their affinity of interest. Secondly, the glycopolymer’s ability to achieve complexation of single-wall carbon nanotubes (SWCNTs) was demonstrated in aqueous environment. Particularly, it was discovered that disaccharide lactose-containing polymers with dense carbohydrate pendent units and long backbones allowed for the best performance, which revealed the synergistic effects of carbohydrate identity and polymer chain length on introducing water solubility to SWCNTs. It was discovered that that the dispersion of SWCNTs with the novel N-glycan polymers yielded even greater water solubility than that with the well-known and conventional dispersant – DNA-(GT)20. Finally, the immunomodulation effects of the novel synthetic N-glycan polymers were compared with model compound, lipopolysaccharide, upon treatment of mouse macrophages using a series of newly developed high-throughput multiplex assays on micropillar chips and 384-pillar plates platforms, which are validated using conventional 96-well plates. vi TABLE OF CONTENTS Page ABSTRACT .........................................................................................................................v LIST OF TABLES ........................................................................................................... xiii LIST OF FIGURES ......................................................................................................... xiv LIST OF SCHEMES....................................................................................................... xvii ABBREVIATION.......................................................................................................... xviii CHAPTER I. INTRODUCTION .........................................................................................................1 1.1 Glycans ........................................................................................................1 1.1.1 Glycosylation .......................................................................4 1.1.2 Sialic Acids ..........................................................................5 1.1.3 Sialic Acid Recognition and Siglecs ....................................8 1.2 Biomimetic Glycopolymers .......................................................................10 1.3 Synthesis of Sialo-glycopolymers..............................................................12 1.4 Structure of Sialo-glycopolymers ..............................................................12 1.5 Application of Sialo-glycopolymer............................................................24 1.6 Research Rational ......................................................................................24 II. ARYL AZIDE CHAIN-END FUNCTIONALIZED N-LINKED GLYCAN POLYMERS AS PHOTO-ACTIVATABLE PROBES FOR PROTEIN SPECIFICITIES ...........................................................................................................28 2.1 Introduction ................................................................................................28 2.1.1 Cyanoxyl Mediated Free Radical Polymerizations ............30 vii 2.1.2 Aryl Azide Chain-end Functionalization ...........................32 2.2 Experimental ..............................................................................................33 2.2.1 Materials and Methods .......................................................33 2.2.2 Synthesis of Arylamide Glycomonomers ..........................34 2.2.3 Synthesis of Aryl Azide Chain-end Functionalized N- glucosyl Polymer and N-galactosyl Polymer .....................34 2.2.4 Synthesis of Aryl Azide Chain-end Functionalized N- Lactosyl Polymer ...............................................................35 2.2.5 Synthesis of Aryl Azide Chain-end Functionalized Polyacrylamide ..................................................................36 2.2.6 UV-induced Photo-crosslinking Assay ..............................36 2.2.7 SDS-PAGE ........................................................................36 2.3 Results and Discussion ..............................................................................37 2.3.1 Polymer Structure and Saccharide Density Determined by 1H NMR Spectra ................................................................37
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