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Stony Brook University SSStttooonnnyyy BBBrrrooooookkk UUUnnniiivvveeerrrsssiiitttyyy The official electronic file of this thesis or dissertation is maintained by the University Libraries on behalf of The Graduate School at Stony Brook University. ©©© AAAllllll RRRiiiggghhhtttsss RRReeessseeerrrvvveeeddd bbbyyy AAAuuuttthhhooorrr... Tumor-targeting Drug Delivery System of Anticancer Agent A Dissertation Presented by Shuyi Chen to The Graduate School in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Chemistry Stony Brook University May 2008 Copyright by Shuyi Chen 2008 Stony Brook University The Graduate School Shuyi Chen We, the dissertation committee for the above candidate for the Doctor of Philosophy degree, hereby recommend acceptance of this dissertation. Iwao Ojima – Dissertation Advisor Distinguished Professor, Department of Chemistry Nicole S. Sampson – Chairperson of Defense Professor, Department of Chemistry Robert C. Kerber – Third Member Professor, Department of Chemistry George A. Ellestad – Outside Member Senior Research Scientist, Department of Chemistry Columbia University This dissertation is accepted by the Graduate School Lawrence Martin Dean of the Graduate School ii Abstract of the Dissertation Tumor-targeting Drug Delivery System of Anticancer Agent by Shuyi Chen Doctor of Philosophy in Chemistry Stony Brook University 2008 Cancer has become the leading cause of death in the U.S. for people under the age of 85. Current cancer chemotherapy relies on the premise that tumor cells are more likely to be killed by the cytotoxic agents because of their rapidly proliferating. Unfortunately, many anticancer drugs cannot differentiate normal cells from tumor cells, which would iii cause severe undesirable side effects. Accordingly, tumor-targeting drug delivery systems of anticancer agents have attracted extensive attention in cancer chemotherapy. A novel molecular missile, where biotin was applied as a tumor-targeting ligand for receptor-mediated endocytosis, was explored for the efficient delivery of the anticancer agent, 2nd-generation taxoid SB-T-1214. To further investigate the tumor-targeting process and drug release mechanism, several fluorescence-labeled drug conjugates were designed and synthesized. The cellular uptakes of these conjugates were assayed in a leukemia cancer cell line “L1210FR” by confocal fluorescence microscopy (CFM). The cytotoxicity of the tumor-targeting drug conjugate was also assayed against several different types of cells. Additionally, single-walled carbon nanotube (SWNT) was introduced to this biotin- mediated drug delivery system. Functionalized SWNT can serve as efficient drug delivery platform for potential application to tumor-targeting chemotherapy, taking advantage of enhanced permeability and retention (EPR) effect associated with nanomaterials. We have unambiguously demonstrated the occurrence of the designed cancer-specific receptor-mediated endocytosis of the whole conjugate, followed by efficient drug release and binding of the drug to the target protein by confocal fluorescence microscopy (CFM) in the leukemia cell line “L1210FR”. The cytotoxicity of these functionalized SWNT conjugates were assayed against several different types of cells. The results have unambiguously demonstrated the occurrence of the designed cancer-specific receptor-mediated endocytosis of the whole conjugate, followed by efficient drug release and binding of the drug to the target microtubules. The conjugate shows the specificity to the cells with their surface over-expressed with the biotin iv receptor. The cytotoxicity of the conjugate comes from the released taxoid molecues inside the cells. v Table of Contents List of Figures…………………………………………………….…………………….viii List of Schemes………………………………………………….………………………xii List of Tables…………………………………………………………………………....xiv List of Abbreviations………………………………………………….…………………xv Acknowledgements…………………………………………………………….……….xix Chapter I Anticancer Drug Paclitaxel and β-Lactam Synthon Method §1.1. INTRODUCTION: CANCER AND CANCER CHEMOTHERAPY .......................1 §1.2. ANTICANCER DRUG PACLITAXEL.....................................................................2 §1.2.1. Discovery and Development...........................................................................2 §1.2.2. The Biological Role of Paclitaxel...................................................................2 §1.2.3. The Production of Paclitaxel...........................................................................5 §1.2.4. Structure-Activity Relationship (SAR) Studies..............................................7 §1.3. β-LACTAM SYNTHON METHOD..........................................................................8 §1.3.1. Introduction.....................................................................................................8 §1.3.2. Results and Discussion ...................................................................................9 §1.3.2.1. Asymmetric Synthesis of Enantiopure β-Lactam via Chiral Ester Enolate-Imine Cyclocondensation.......................................................9 §1.3.2.2. Synthesis of Enantiopure β-Lactams via Staudinger Reaction Followed by Enzymatic Kinetic Resolution......................................11 §1.3.2.3. Synthesis of 2nd-Generation of Taxoids by β-LSM ...........................13 §1.4. EXPERIMENTAL SECTION..................................................................................15 Chapter II Synthesis of C3’-Difluorovinyl Taxoid SB-T-12852 §2.1. INTRODUCTION ....................................................................................................25 §2.2. RESULTS AND DISCUSSION...............................................................................28 §2.2.1. Synthesis of 4-Difluorovinyl β-Lactam ........................................................28 §2.2.2. Synthesis of C3’-Difluorovinyl 2nd-Generation Taxoid SB-T-12852 ..........29 §2.2.3. Biological Evaluation of Difluorovinal Taxoid SB-T-12852 .......................29 §2.3. EXPERIMENTAL SECTION..................................................................................30 vi Chapter III Biotin-mediated Endocytosis of Fluorescein-labeled Anticancer Agent §3.1. INTRODUCTION ....................................................................................................34 §3.1.1. Tumor-Targeting Delivery of Cytotoxic Drug .............................................34 §3.1.2. Tumor Recognition Moiety...........................................................................36 §3.1.3. Cytotoxic Agents as Warhead.......................................................................41 §3.1.4. Linker Pool....................................................................................................43 §3.2. RATIONAL DESIGN OF TUMOR-SPECIFIC PRODRUG ..................................48 §3.2.1. Previous Achievements of Disulfide-Containing Prodrugs..........................48 §3.2.2. Novel Disulfide Linkers for Efficient Drug Release ....................................50 §3.2.3. Biotin as Tumor Recognition Moiety ...........................................................52 §3.2.4. Coupling Ready Warhead.............................................................................54 §3.2.5. Fluorescent Probes for Evaluation of Intracellular Drug Release ................55 §3.3. RESULTS AND DISCUSSION...............................................................................59 §3.3.1. A New Class of Disulfide Linkers................................................................59 §3.3.1.1. Synthesis of Disulfide-Containing Linkers .......................................60 §3.3.1.2. Kinetic Study of Model Drug Release Profile...................................57 §3.3.2. Fluorescence-Tagged Molecular Probes.......................................................72 §3.3.2.1. Synthesis of Fluorescence-Tagged Molecular Probes.......................73 §3.3.2.2. In Vitro Evaluation of Fluorescence-Tagged Molecular Probes ......76 §3.4. EXPERIMENTAL SECTION..................................................................................83 Chapter IV Functionalized SWNT (f-SWNT) as Transporter for Tumor-targeting Drug Delivery §4.1. INTRODUCTION ..................................................................................................100 §4.1.1. Nanomedicine .............................................................................................100 §4.1.2. Carbon Nanotubes (CNT)...........................................................................107 §4.1.2.1. Toxicity and Pharmacological Studies of CNT:..............................108 §4.1.2.2. Surface Chemistry of CNT ..............................................................110 §4.1.3. Functionalized CNT as Drug Delivery Platform ........................................112 §4.2. RESULTS AND DISCUSSION.............................................................................116 §4.2.1. Rational Design of f-SWNT as Transporter for Drug Delivery .................116 §4.2.2. Syntheses and Structure Characterization of f-SWNT-based Conjugate....119 §4.2.3. Biological Evaluation of Functionalized f-SWNT-based Conjugate..........125 §4.3. EXPERIMENTAL SECTION................................................................................134 §4.3.1. Syntheses of Functionalized SWNTs..........................................................134 §4.3.2. Confocal Microscopy, Flow Cytometry and Cytotoxicity Analysis...........137 §4.4. PERSPECTIVE: COMBINATION
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